The International Observer’s 100 Greatest Songs of All Time


No two people could possibly agree on which songs are the greatest of all time. That didn’t stop us from debating and compiling a list of our choices. Disagree? That’s why the comments section was invented.

#100: “Round Midnight”

Year: 1944

Performer: Thelonius Monk

Writer: Thelonius Monk

Appears on: The Essential Thelonius Monk

It seems likely that Thelonius Monk suffered from mental illness during his life, perhaps bipolar disorder. If so, it’s likely that that enabled his marvelous creativity. This song was astoundingly composed by Monk when he was just 18 years old and it takes the listener inside his inner turmoil, making you feel as though you’re having a conversation in a bar at three in the morning.

Miles Davis made a famed cover version of the song (called ‘Round About Midnight) and made an historic performance of the song at the 1955 Newport Jazz Festival.

#99: “A Day in the Life”

Year: 1967

Performer: The Beatles

Writer: John Lennon and Paul McCartney

Appears on: Seargant Pepper’s Lonely Hearts Club Band

The impetus behind the Beatles’ masterpiece was a Daily Mail article about the death of an heir to the Guinness’ beer fortune in a car accident. He was familiar to all The Beatles before his death.

Image result for tara browne newspaper

The song climaxes one of the great records in rock history – Seargent Pepper’s Lonely Hearts Club Band – and in fitting fashion with a full orchestra and plenty of surprises along the way.

The song was pieced together from different snippets written by both John and Paul. Can it be said to have a specific meaning? Maybe and maybe not. The song passes through a man reading a newspaper, going through the ordinary motions of a morning, and slipping in and out of contemplation and experience. If there is any kind of theme connecting these stories, it’s the kind of detachment that can easily be felt in the modern world where each day’s newspapers bring a fresh round of absurdity.

Regardless of the meaning you attach to it, “A Day in the Life” ushered in the era of the epic rock song.

#98: “Fables of Faubus”

Year: 1959

Performer: Charles Mingus

Writer: Charles Mingus

Appears on: Mingus Ah Um

Many have said that Arkansas Governor Orval Faubus was actually not a segregationist and that his refusal to honor the Supreme Court’s decision in Brown v. Board of Eduction was purely a political stunt. In the end, it really didn’t matter and Charles Mingus took no mercy on the man who tried to prevent children from attending school. A hundred years from now people will probably remember little about his life – but they will probably still listen to Mingus shred him.

#97: “Dancing In The Street”

Year: 1964

Performer: Martha and the Vandellas

Writer: Marvin Gaye, Mickey Stevenson, and Ivy Jo Hunter

Appears on: The Definitive Collection

Intended or not, “Dancing in the Streets” hit the country just as the Civil Rights Movement was maturing and the lyrics to the song would take on deep meaning over the later part of the 1960s. Aside from that, this song is one of the most fun things to listen to and can still drive people to get up and dance to this day.

Regardless of your politics, we could probably all stand to dance just a little more.

#96: “My Favorite Things:

Year: 1961

Performer: John Coltrane

Writer: Richard Rodgers

Appears on: My Favorite Things

Who would have thought that a Rodgers and Hammerstein song from The Sound of Music could become a jazz classic in the hands of John Coltrane? Even more remarkable was Coltrane’s choice to play the soprano saxophone on the record. No jazz saxophonist had contemplated that before. (The saxophone was purchased by Miles Davis while the two were touring Europe together.)

The recording was one of many courageous choices that Coltrane made in his all too short career that changed jazz music and the how the saxophone itself is perceived.

#95: “I Feel Like Going Home”

Year: 1948

Performer: Muddy Waters

Writer: Muddy Waters

Appears on: Essential Original Albums

Born in Mississippi, Muddy Waters would take the Delta Blues north to Chicago and become one of the great blues performers ever. Among his future accomplishments was recording the song that gave both the Rolling Stones band and Rolling Stone magazine their name. This song, about a man who feels like dying since his girl left him, was the song that established Waters’ reputation throughout the many blues clubs in which he performed.

#94: “God Bless the Child”

Year: 1939

Performer: Billie Holiday

Writer: Billie Holiday and Arthur Herzog, Jr.

Appears on: Lady Day: Essential Original Albums

The woman who would have a greater influence on how vocalists approached songs than any other (without her most songs would be much more boring than they actually are) was born in Philadelphia in 1915. A difficult childhood in which her father abandoned her led to her and her mother moving to Harlem where they both were prostitutes. Years later Billie Holiday lent her mother the money she needed to start a restaurant, but when situations were reversed her mother refused to help her by lending her the money she needed.

Holiday turned this experience into the incredibly powerful “God Bless the Child”. The song mourns how those with resources scorn those without, even implying that religion is no cure for selfishness. Seventy-eight years after its recording, we all would probably be better people if we let this song seep into our hearts.

#93: “Giant Steps”

Year: 1960

Performer: John Coltrane

Writer: John Coltrane

Appears on: Giant Steps

If anyone aspires to play the saxophone, the first thing they should do is listen to “Giant Steps”. Your first inclination is to ask yourself, “How can someone play that quickly?” Once you know a little more music you’ll be even more amazed that he’s playing that fast while moving between three keys.

We are likely to agree that A Love Supreme is Coltrane’s magnum opus, but Giant Steps was his first true masterpiece and the entire record sounds unbelievably fresh to this day.

#92: “Abandoned Love”

Year: 1975

Performer: Bob Dylan

Writer: Bob Dylan

Appears on: Nowhere that we know of

Bob Dylan had the strange habit of leaving some of his best work off of commercial releases. This may have begun with the song “Let Me Die In My Footsteps”, an incredibly powerful song in the age of the Cuban Missile Crisis. The problem was that Dylan developed so quickly that by the time he could finish his second album he had already surpassed this small masterpiece with the likes of “Blowin’ in the Wind” and “A Hard Rain’s A-Gonna-Fall”. It’s even more astonishing that a song like “Mama, You’ve Been On My Mind” was left off Another Side of Bob Dylan.

“Abandoned Love” was eventually recorded but in a wildly inferior form to this version recorded at the Bleecker Street club “The Other End.” We can only presume that the song is sung for his wife Sara, whom he divorced in 1977. There are a lot of breakup songs and songs of lost love, but it’s hard to conceive of one more perfect than this, that concludes with the line, “let me feel your love one more time before I abandon it.”

#91: “Where Did You Sleep Last Night?”

Year: 1994

Performer: Nirvana

Writer: Traditional, arr. by Mark Lonegan

Appears on: Unplugged

Kurt Cobain introduced this song by giving Leadbelly his due, but he ends it by leaving the audience giving him his. MTV wanted an encore, but Cobain realized he would never top the performance he had just given. The performance was taped on November 18, 1993, and Cobain was dead less than five months later on April 8, 1994.

#90: “Blue Eyes Crying in the Rain”

Year: 1975

Performer: Willie Nelson

Writer: Fred Rose

Appears on: Red Headed Stranger

Willie Nelson first achieved fame by penning the classic “Crazy” that was recorded by Patsy Cline. But it was not until he signed a contract with Atlantic Records and released the album Shotgun Willie in 1973 that he achieved fame as a performer. Red Headed Stranger was the follow up and included this cover of a Fred Rose song about an old man remembering of a youthful love that was never replicated. All he has left is the hope of soon seeing her in heaven.

It may have helped launch Nelson’s career, but the song also took an emotional toll on Nelson who sang the song night after night, perhaps never thinking that an album of covers of old country songs would have such a lasting impact.

#89: “You Don’t Know Me”

Year: 1962

Performer: Ray Charles

Writer: Cindy Walker

Appears on: Modern Sounds in Country and Western Music

Viewers of the film Ray became aware of the painful life that Ray Charles led and the struggles that led to the beautiful breadth of music he created. In the late Autumn of 1961 Charles was arrested for possession of heroin. The charges were later dropped, but the incident cast a pall over Charles and his announcement that he was planning to cover country and western songs for his next record. The resulting record, though, was an absolute classic that combined Charles’ voice with somber country classics.

This song about a man unable to get out of the “friend zone” has been covered by many artists, but no version has exceeded this one.

#88: “The Night They Drove Old Dixie Down”

Year: 1969

Performer: The Band

Writer: Robbie Robertson

Appears on: The Band

The great Ken Burns documentary The Civil War includes an interview with the late Shelby Foote where he says:

As a Southerner I would say one of the main importances of the war is that Southerners have a sense of defeat which none of the rest of the country has.  You see in the movie Patton, the actor who plays Patton saying, “We Americans have never lost a war.” That’s a rather amazing statement for him to make as Patton because Patton’s grandfather was in Lee’s army of Northern Virginia and he certainly lost a war.

Virgil Kane definitely knows what it’s like to lose a war too. After spending the previous four years believing in a cause, he’s left with nothing when all comes crashing down. Perhaps we would all do well to examine movements more closely before signing ourselves up to them.

#87: “Everlong”

Year: 1997

Performer: Foo Fighters

Writer: Dave Grohl

Appears on: The Colour and the Shape

Dave Grohl wrote this song for Louise Post during the mid-1990s at a time when Foo Fighters had started to drift somewhat. It later became David Letterman’s favorite song and the band came on his show to sing it both when Letterman returned from heart surgery and as the last musical performance of the show.

The lyrics to the song…”breathe out, so I can breathe you in”…are some of the best Grohl has ever written. He once humorously told of his encounter with Bob Dylan, completely dressed in black in a dark room, who said to him of the song, “that’s pretty good.”

#86: “Jolene”

Year: 2004

Performer: Ray LaMontagne

Writer: Ray LaMontagne

Appears on: Trouble

The 2004 release of the album Trouble established Ray LaMontagne as an original songwriter with a strikingly unique and beautiful voice. This song, later covered by the Zac Brown Band, stands out among LaMontagne’s eclectic repertoire. Of course there was another song about a “Jolene” that could also be said to be about a dependent relationship, but to our knowledge LaMontagne has never commented on the song, so any connection is pure supposition on our part.

This “Jolene” seems to be about a man whose made mistakes in his life and a woman is all that keeps him trying to improve through the alcohol and drugs. If you’ve never heard it, listen to it. If it doesn’t move you then you’re dead inside.

#85: “Dark Was the Night, Cold Was the Ground”

Year: 1927

Performer: Blind Willie Johnson

Writer: Blind Willie Johnson

Appears on: The Complete Blind Willie Johnson

Blind Willie Johnson really was blind. When he was young his mother accidentally threw lye into his eyes, permanently blinding him. He became an evangelical preacher and among the greatest slide guitarists of all time. He died shortly after the end of the second world war after he caught pneumonia in Beaumont, Texas.

“Dark Was the Night, Cold Was the Ground” was about the crucifixion, in keeping with Johnson’s spiritual interests. It drew influence from a folk song called “Gesthemane” whose opening lines were borrowed for the title of this song.

#84: “I Hung My Head”

Year: 2002

Performer: Johnny Cash

Writer: Sting

Appears on: American IV: The Man Comes Around

Johnny Cash’s final several albums were extraordinary and signified a remarkable return to relevance for the country legend. You would probably never guess it to listen to the song, but it was authored and originally recorded by Sting and grew out of his love of Westerns.

The story of an accidental shooting and the tragedy that ensues is a reminder of how precarious our own lives can be – constantly one mistake from losing everything and falling upon spirituality to give meaning to the absurdity.

#83: “Nightswimming”

Year: 1992

Performer: R.E.M.

Writer: R.E.M.

Appears on: Automatic for the People

R.E.M. had songs more famous than this one, but “Nightswimming” has a sentimentality that is difficult to remove from yourself after you’ve become acquainted with the song. It may be about skinny dipping, but “Nightswimming” is more generally about those random memories of being a teenager that never leave you and that you return to time and again throughout your life as a benchmark of the progress, or lack thereof, that you’ve made. Or simply a means to relive moments that you know in your brain have died but that your heart has not yet realized.

#82: “Someone Saved My Life Tonight”

Year: 1975

Performer: Elton John

Writer: Elton John and Bernie Taupin

Appears on: Captain Fantastic and the Brown Dirt Cowboy

Before he was Elton John, Reginald Dwight was engaged to be married to a woman, while suffering immense confusion regarding his own sexuality and plans for his life. For a time he considered committing suicide. Instead, a friend convinced him to withdraw from the engagement and focus on his musical career.

Bernie Taupin’s lyrics recall how close Elton John may have been to ending it before he ever really began and is an ode to the power of friendships throughout life.

#81: “Sometimes”

Year: 1991

Performer: My Bloody Valentine

Writer: Kevin Shields

Appears on: Loveless

Everything about the song “Sometimes” feels like a dream. In fact, the same can be said about the entire album Loveless, whose reputation has consistently grown since its 1991 release.

This was effectively used in the 2003 film Lost in Translation, and Kevin Shields contributed new compositions to the soundtrack as well. This is a song you just have to listen to and allow yourself to feel. It is the musical equivalent to the Nietzsche quote, “That which can be said is something already dead in our hearts.”

#80: “Lover, You Should Have Come Over”

Year: 1994

Performer: Jeff Buckley

Writer: Jeff Buckley

Appears on: Grace

Jeff Buckley’s accidental death in 1997 while swimming near Memphis is one of the great tragedies of modern music. He only recorded one album in his lifetime, but that one album, Grace, is better than the entire career output of many other musicians.

His father Tim Buckley was a famous folk singer and Buckley started to gain a following by plaing at New York clubs such as the East Village’s Sin-e.

“Lover You Should Have Come Over” was written after Buckley’s break up with fellow musician Rebecca Moore. It takes a unique perspective to a break-up – rather than spewing anger at the other party, Buckley expresses dissapointment in himself at being affected by the break-up in the way that he is.

#79: “He Stopped Loving Her Today”

Year: 1980

Performer: George Jones

Writer: Bobby Braddock and Curly Putmam

Appears on: I Am What I Am

Some believe “He Stopped Loving Her Today” is the greatest country music song of all time. Those people are wrong. That title should rightly go to Hank Williams’ “I’m So Lonesome I Could Cry.” But, that doesn’t stop this George Jones classic from being one of the most devastating songs ever recorded. It tells the story of a man whose never able to get over a particular woman until he dies, which is the day he stops loving her.

#78: “Crazy In Love”

Year: 2004

Performer: Beyonce and Jay-Z

Writer: Beyonce, Jay-Z, Rich Harrison, and Eugene Record

Appears on: Dangerously in Love

Five years before they married, Beyonce and Jay-Z teamed up to make one of the most infectious and memorable pop songs ever. Funk, pop, soul, and rap all layer on top of each other until a new sound emerges.

This song was Beyonce’s first success after leaving Destiny’s Child.

#77: “One of Us Cannot Be Wrong”

Year: 1967

Performer: Leonard Cohen

Writer: Leonard Cohen

Appears on: Songs of Leonard Cohen

If we had to guess, “One of Us Cannot Be Wrong” could be one amongst a handful of songs on this list that you have never heard before. If it is, you should listen to it right away. The song is confirmation of the beautiful poetical soul that Leonard Cohen possessed.

It is generally agreed upon that the song was written about the intoxicating Nico, who sang with The Velvet Underground and was a fashion model. Despite the graveyard of bodies from failed attempts to conquer her, Cohen presses on in the hopes that one person will be right to do so.

#76: “Christmas Card From a Hooker in Minneapolis”

Year: 1978

Performer: Tom Waits

Writer: Tom Waits

Appears on: Blue Valentine

Is this song a tragedy or a comedy? With Waits you normally don’t know. There are moments that this song makes you want to laugh out loud, but by the punchline no one is laughing anymore.

The inspiration comes from a poem called “Charlie I’m Pregnant” by Charles Bukowski. The writer of the note in the song is a prostitute who tells a former john about how great her life has become before confessing that she’s made the whole thing up and is writing from prison.

#75: “Love Will Tear Us Apart”

Year: 1979

Performer: Joy Division

Writer: Ian Curtis

Appears on: Substance

On May 18, 1980, Ian Curtis, the lead singer of Joy Division committed suicide by hanging himself. He had suffered from epileptic seizures and depression and the medicine he took to control his seizures only made his depression worse.

This was the best song Curtis wrote, an ironic homage to “Love Will Keep Us Together,” it documents the state-of-mind of the singer in his final months and the challenges of his young marriage.

#74: “We Shall Overcome”

Year: 1947

Performer: Pete Seeger

Writer: Traditional

Appears on: Pete Seeger’s Greatest Hits

When Lyndon Johnson introduced the Voting Rights Act to Congress he said:

“Even if we pass this bill, the battle will not be over. What happened in Selma is part of a far larger movement which reaches into every section and state of America. It is the effort of American Negroes to secure for themselves the full blessings of American life. Their cause must be our cause, too. Because it is not just Negroes, but really it is all of us, who must overcome the crippling legacy of bigotry and injustice. And we shall overcome.”

It would have been unthinkable that a President of the United States would have quoted a Civil Rights anthem in an address to Congress only a few years prior, but such is the power of this song and what can be accomplished when people are willing to allow themselves to be changed.

#73: “The City of New Orleans”

Year: 1972

Performer: Arlo Guthrie

Writer: Steve Goodman

Appears on: Hobo’s Lullaby

Steve Goodman wrote this song while riding the Illinois Central with his wife. After the trip, he heard the train was going to be decommissioned and he added the melody and recorded it as a way to encourage the railroad to change its mind. He was eventually able to play the song for Arlo Guthrie who also recorded it and Willie Nelson recorded a popular version in the 1980s.

It is said that the line “Good morning America, how are you?” gave the ABC morning news show its name.

#72: “Dancing Queen”

Year: 1976

Performer: Abba

Writer: Abba

Appears on: Arrival

Whether you want to admit it or not, when you take a look at Abba’s catalog the talent of the band sneaks up on you. “Mamma Mia” spawned a Broadway show and Madonna heavily sampled “Gimme! Gimme! Gimme! (A Man After Midnight)” in her song “Hung Up.” “Dancing Queen” was Abba’s only chart-topping hit in the United States and featured a disco inspired contagious beat, with a gorgeous melody laid over top of it, allowing it to transcend much of the disco music being made at the time and later forgotten.

#71: “No One”

Year: 2007

Performer: Alicia Keys

Writer: Alicia Keys, Kerry Brothers, Jr., and George Harry

Appears on: As I Am

Alicia Keys is one of a small handful of twenty-first-century musicians to be bonafide geniuses. Her voice rivals anything found in classic soul records, her piano playing is as accomplished as any other popular musician, and her songwriting has consistently been a cut-above. It’s always debateable what music from the current environment will be around and listened to several decades from now, but it seems hard to think that people won’t still be listening to Alicia Keys in the 22nd century.

#70: “Mr. Tambourine Man”

Year: 1965

Performer: Bob Dylan

Writer: Bob Dylan

Appears on: Bringing it all Back Home

Hunter S. Thompson loved this song so much that he made the dedication to Fear and Loathing in Las Vegas: “To Bob Geiger, for reasons that need not be explained here – and to Bob Dylan, for Mister Tambourine Man.” The song was played at his funeral. It’s hard not to hear the final verse and compare it to some of the most beautiful poetry that’s ever been written:

“Take me dissapearing through the smoke rings of my mind

Down the foggy ruins of time

Far past the frozen leaves

The hautened, frightened trees

Out to the windy beach

Far from the twisted reach of crazy sorrow

Yes, to dance beneath the diamond sky

With one hand waving free

Silhouetted by the sea

Circled by the circus sands

With all memory and fate

Driven deep beneath the waves

Let me forget about today until tomorrow”

Dylan was certainly influenced by Rimbaud in ways he hadn’t previously been, but the final scene of La Strada on the beach also seems to have provided inspiration.

#69: “Blue in Green”

Year: 1959

Performer: Miles Davis

Writer: Miles Davis

Appears on: Kind of Blue

Kind of Blue is one of the miraculous moments in music. Most music has traditionally been built on chords that provide the harmony underneath the primary melody. This was equally true of jazz, where a soloist would provide a melody with the rest of the band improvising chord changes as accompaniment. A “mode” is nothing more than a musical “scale,” each scale representing a particular key. The songs on Kind of Blue continued the approach Davis and his band had taken previously on Milestones, where the underlying structure of improvisation accompanying the soloist was built on these scales rather than chord changes.

“Blue in Green” is arguably the best track of the record, with a near perfect piano piece from Bill Evans and soft, slow, and subtle playing from both Davis and John Coltrane.

#68: “Helpless”

Year: 1970

Performer: Crosby, Stills, Nash & Young

Writer: Neil Young

Appears on: Deja Vu

Neil Young did not have the easiest childhood. Born in Ontario, Canada, he had polio by the age of six and his parents divorced when he was a teenager. The song “Helpless” remembers these early days of Young’s life and reflects a bittersweet existence in the way only a Neil Young song could.

#67: “Creep”

Year: 1993

Performer: Radiohead

Writer: Thom Yorke

Appears on: Pablo Honey

Radiohead’s breakout success was written before the band was famous and while Thom Yorke was a still a college student. It tells the story of an infatuation in which he finally concedes he does not feel good enough for the object of his desire. While the singer describes himself as a “creep,” it’s a feeling all but the most self-assured of us can relate to at one time or another.

The song was so popular, Radiohead actually grew tired of playing it in concerts.

#66: “Suspicious Minds”

Year: 1969

Performer: Elvis Presley

Writer: Mark James

Appears on: From Elvis in Memphis

In 1962, Elvis Presley’s “Good Luck Charm” reached the top of the pop charts in the United States. There was nothing unusual about that, it was Presley’s 17th chart-topping single since entering the mainstream of American music in 1956. But few would have predicted that it would be seven years before he would reach the top of the charts again. In fact, he would have noticeably few records that would receive large amounts of airplay and only four records would reach the top five (“She’ Not You,” “Return to Sender,” “Devil in Disguise,” and “Crying in the Chapel”) until he mounted a comeback in 1969. After selling out in Hollywood for years, Elvis returned for a classic music special in 1968 and reinvented himself with several successful singles the following year. “Suspicious Minds” was Elvis Presley’s 18th and final number one hit in the United States.

#65: “St. Thomas”

Year: 1956

Performer: Sonny Rollins

Writer: Sonny Rollins

Appears on: Saxaphone Colossus

Sonny Rollins is one of the great saxophonists who ever lived, deserving of inclusion in a conversation with Charlie Parker and John Coltrane. Famously, he grew unsatisfied with his artistic direction and stopped recording to play day after day on the Williamsburg Bridge. “St. Thomas” was recorded several years before that episode and was based on a nursery rhyme Rollins heard when he was young called, “The Lincolnshire Poacher.”

The song is heavily influenced by carribean and calypso music and the title refers to the island of St. Thomas in the Virgin Islands.

#64: “Long, Long, Long”

Year: 1968

Performer: The Beatles

Writer: George Harrison

Appears on: The White Album

The sheer volume of classic songs that the Beatles recorded can make it easy to forget a gem like George Harrison’s “Long, Long, Long.” It is one of Harrison’s most touching compositions, drawn from his quest to reconcile himself to a God he could believe in. Prior to composition, Harrison and the other Beatles traveled with the Mahareshi Mahesh Yogi to study meditation. Harrison seems to have been the only member of the group to continue believing in Eastern religions and meditation following their return to England. The melody of the song was based on Bob Dylan’s “Sad Eyed Lady of the Lowlands.”

#63: “Stones In My Passway”

Year: 1937

Performer: Robert Johnson

Writer: Robert Johnson

Appears on: The Complete Recordings

There is a famous story that the Rolling Stones tell about first discovering Robert Johnson. For some time they assumed that there was more than one guitarist playing because they didn’t think it was possible for one person to play as Johnson did. When Eric Clapton recorded this song, he spoke about his difficulty mastering it throughout his life. In one section in particular the time signature of the singing and guitar playing are not the same and Clapton was never able to sing the song and play it without accompaniment. That’s pretty astonishing considering how gifted Clapton is.

The lyrics to the song are profound as well, detailing a man who no longer has control over himself and feels that he’s long ago lost his soul.

#62: “1979”

Year: 1995

Performer: The Smashing Pumpkins

Writer: Billy Corgan

Appears on: Mellon Collie and the Infinite Sadness

Billy Corgan was 12 years old in 1979 and would later say that the year was transformative for him. It’s hard for anyone not to identify with the lyrics about getting older and feeling exhilarated, confused, and lost all at the same time.

The song nearly didn’t make the cut for Melon Collie and the Infinite Sadness and was only included after being re-worked at the last minute. It may be the most recognizable Smashing Pumpkins song today with a fantastic music video to compliment it as well.

#61: “Stand By Me”

Year: 1961

Performer: Ben E. King

Writer: Ben E. King, Jerry Lieber, and Mike Stoller

Appears on: Stand By Me: The Platinum Collection

Whether you measure the appearances in movie soundtracks, cover versions, or royalties, “Stand by Me” is one of the most enduring songs to have ever been written. Co-writer, singer and Drifters member Ben E. King reflected in later years on the spiritual aspects to the song in addition to its obvious reflections on love and friendship.

The best interpretation of the song based upon the text itself is that it is about friendship with God, as it is obviously influenced by the 46th Psalm:

God is our refuge and strength,
    an ever-present help in trouble.
 Therefore we will not fear, though the earth give way
    and the mountains fall into the heart of the sea,
though its waters roar and foam
    and the mountains quake with their surging.”

Of course, the 1986 movie of the same name would forever link the song to being about close friendships that stay with us for a lifetime.

#60: “Empire State of Mind”

Year: 2007

Performer: Jay-Z and Alicia Keys

Writer: Angela Hunte and Jane’t Sewell-Ulepic

Appears on: The Blueprint 3

At the intersection of the Brooklyn neighborhoods of Borerum Hill, Park Slope, and Fort Greene stands an apartment building that both Jay-Z and Angela Hunte, a co-writer of the song, once lived in.

“Empire State of Mind” is a modern take on the primary reasons why New York City has risen to a powerful city and powerful metaphor even for those who do not live there: it’s primary purpose as a home to communities from all over the world and it’s beacon as a place where anything is possible and anyone can go to reinvent themselves.

#59: “What A Wonderful World”

Year: 1967

Performer: Louis Armstrong

Writer: Bob Thiele and George David Weiss

Appears on: All Time Greatest Hits

Despite this song being offered to Tony Bennett initially, it was written with Louis Armstrong in mind as someone who was able to help heal divides and reach multi-ethnic audiences.

Today, the song is a standard and was eventually recorded by Tony Bennett, although we can only imagine how events would have played out if Bennett did not initially turn down the song.

This is another beautiful song that the late Eva Cassidy put her indelible stamp on.

#58: “Hold On”

Year: 1999

Performer: Tom Waits

Writer: Tom Waits

Appears on: Mule Variations

According to Waits, part of the song “Hold On” was inspired by viewing a transgender dancer, dancing by themselves at a street corner on a cold day. Waits’ daugter, seeing the same scene, commented, “It must be really hard to dance like that when you’re so cold and there’s no music.”

Waits’ exquisite song generalizes this observation. We all hold on to something – some illusion, belief, or even outright lie – to make it through the topsy-turvy lives we are forced to lead.

The album Mule Variations in which “Hold On’ appears resurrected Waits’ career after a six year hiatus.

#57: “Chelsea Hotel #2”

Year: 2006

Performer: Rufus Wainwright

Writer: Leonard Cohen

Appears on: I’m Your Man

Leonard Cohen let slip that this song was written about a fling he had with Janis Joplin in New York’s Chelsea Hotel, and then regretted doing so for the rest of his life. The hotel was once a mecca for important artists including Bob Dylan (whose “Visions of Johanna” and “Sad Eyed Lady of the Lowlands” were written there), Allen Ginsburg, Sid Vicious (where his girlfriend was murdered), Madonna, and Stanley Kubrick. Currently, the hotel is closed for renovations.

#56: “Where the Streets Have No Name”

Year: 1987

Performer: U2

Writer: U2

Appears on: The Joshua Tree

“Where the Streets Have No Name” is among the most enduring in U2’s catalog. The lyrics were written by Bono after reading that a person’s income and religion in Belfast could be determined by simply having their address. The Edge added a classic introduction that produces an echoing arpeggio thanks to extensive use of delay.

The song is a staple of U2’s live performances, including their performance on the Super Bowl following the September 11th attacks and the spectacular version from Boston in the video above.

#55: “Someone to Watch Over Me”

Year: 1950

Performer: Ella Fitzgerald

Writer: George Gershwin and Ira Gershwin

Appears on: The Great American Songbook

This Gershwin classic was composed for the 1926 musical Oh, Kay! The song has been covered by everyone from Frank Sinatra to Barbara Streisand and Amy Winehouse, but nobody does it justice the way Ella Fitzgerald is able to.

#54: “Feeling Good”

Year: 1965

Performer: Nina Simone

Writer: Anthony Newley and Leslie Bricusse

Appears on: I Put a Spell on You

“Feeling Good” was originally written for the 1964 musical The Roar of the Greasepaint, The Smell of the Crowd, a British musical about the co-dependency of economic classes. Covered by many, Simone’s version from one year after the original is the best. The beautiful cry of emancipation is rightly associated with Simone today.

#53: “My Funny Valentine”

Year: 1955

Performer: Chet Baker

Writer: Richard Rodgers and Lorenz Hart

Appears on: Chet Baker Sings

Like “Feeling Good,” “My Funny Valentine” began life in a Broadway musical. The 1937 hit Babes in Arms features the character Billie Smith singing the song to another character named Valentine. Fifteen years after the musical, Chet Baker and Gerry Mulligan teamed up within the Gerry Mulligan Quarter in what would become an enduring musical relationship between the two men, whose interlocking melodies resurrected classical concepts such as counterpoint and helped invent what came to be called “West Coast Jazz.”

#52: “Wild Horses”

Year: 1971

Performer: The Rolling Stones

Writer: Mick Jagger and Keith Richards

Appears on: Sticky Fingers

The Rolling Stones have had a career of highlights, but even for one of Rock’s most important bands “Wild Horses” is stands above. Keith Richards wrote the sad melody with feelings of guilt for leaving his newborn child alone so frequently while he toured the world. Mick Jagger added the lyrics, which many believe to be about his relationship with Marianne Faithful despite Jagger’s denial.

The song captures the conundrum of powerful relationships: all that it is wonderful is intertwined with all that is painful.

#51: “Like A Rolling Stone”

Year: 1965

Performer: Bob Dylan

Writer: Bob Dylan

Appears on: Highway 61 Revisited

The phrase “a rolling stone gathers no moss” is a very old one, dating to Roman writer Publilius Syrius. Gathering moss was once seen as a good thing – those who build a foundation in a community and contribute are rewarded with the growing moss of a family and possessions; those who roam from one place to another never accumulate anything.

Years later, the advent of Rock ‘n Roll inverted the idiom. Muddy Waters’ song “Rollin’ Stone” was the basis for the name of both the band and the magazine and celebrated the freedom of mobility. Modern connotations see a rolling stone as youthful, creative, and in fulfilling the dreams one sets for oneself, not those imposed by a community.

To which meaning does Dylan impart in “Like A Rolling Stone”? Probably, both. It’s true that the phrase was probably implanted into Dylan through Hank Williams’ song “Lost Highway,” which unambiguously uses it in its historical context. It’s not known who, if anyone specifically, Dylan is singing to, but once you get past the seemingly sneering derision he holds “Miss Lonely” in, you realize that Dylan’s question is actually a sincere one. Is freedom and autonomy worth the sacrifices of family and convention? Each person must give their own answer.

#50: “Trying to Get to You”

Year: 1956

Performer: Elvis Presley

Writer: Rose Marie McCoy and Charles Singleton

Appears on: Elvis Presley

After Elvis Presley’s contract was sold by RCA to Sun, the label combined five of Presley’s unreleased Sun recordings with seven new recordings for his first album. “Trying to Get to You” was one of the five Sun recordings to make it on the record.

An argument can be made that the vocal on “Trying to Get to You” is the best Presley ever recorded and it’s combination with the instantly recognizable riffs of Scotty Moore served a prelude of the greatness and legend to come.

#49: “Bridge Over Troubled Water”

Year: 1970

Performer: Simon and Garfunkel

Writer: Paul Simon

Appears on: Bridge Over Troubled Water

“Silver girl” was once a popular name for a Heroin syringe, leading many to speculate that this song was about drug use. The lyrics may fit that interpreation, but Simon has always denied it and stated that “silver girl” was a joke about his wife.

Regardless how you want to interpret the lyrics, the gospel-tinged song was an instant classic and featured Art Garfunkel’s voice at its most angelic.

#48: “I Want You Back”

Year: 1969

Performer: The Jackson 5

Writer: Berry Gordy, Freddie Perren, Alphonso Mizell, and Deke Richards

Appears on: Diana Ross Presents the Jackson 5

Michael Jackson was only eleven when this song was recorded, but it was already clear that he was destined for greatness. “I Want You Back” was the first of fifteen chart-topping hits he recorded by himself or with his brothers over the next  several decades and somehow “I Want You Back” contains a kind of energy that was never repeated.

The chord progression of the chorus has been celebrated since the release of the song and a major reason why modern hip-hop samples it so frequently. But, the real power of the song comes from the ability of an eleven year old kid to sing as though he understood the meaning of every word.

#47: “People Get Ready”

Year: 1965

Performer: The Impressions

Writer: Curtis Mayfield

Appears on: People Get Ready

Before he was “Superfly,” Curtis Mayfield wrote this extraordinary song while a member of The Impressions. The church inspired lyrics tell of the hope of a train to deliver God’s people to Jordan, the afterlife. In the context of black history and culture, the train can most easily be seen as the Unerground Railroad. Released in the midst of the civil rights struggle, the song framed the struggle more eloquently than any other save “A Change is Gonna Come.”

#46: “The Message”

Year: 1982

Performer: Grandmaster Flash and the Furious Five

Writer: Melle Mel, Sylvia Robinson, Duke Bootee, Clifton Chase, and Richard Henderson

Appears on: Message from Beat Street

After rap and hip hop culture was formed in the Bronx throughout the 1970s, “Rapper’s Delight” by the Sugarhill Gang became the first hip hop song to capture mainstream attention. The song was a reflection of the block parties and break dancing that had become popular in various neighborhoods. But, it was 1982’s “The Message” that firmly established hip hop music as a means of social commentary. The song preceded practically all of the major accomplishments to come including N.W.A. and Public Enemy.

#45: “Back to Black”

Year: 2006

Performer: Amy Winehouse

Writer: Amy Winehouse

Appears on: Back to Black

Amy Winehouse’s last album was also her masterpiece. Back to Black shifted somewhat from the jazz-inspired debut Frank to a sound based more on classic girl groups like The Shirelles. The lyrics were heavily influenced by Winehouse’s tumultous relationship with Blake Fielder-Civil.

The black to which she refers is likely a combination of depression, alcohol, and heroin – black is a popular street name for the drug. Sadly, Amy Winehouse was unable to find the better angels of her nature and died of alcohol poisoning in July, 2011.

#44: “The Grass is Blue”

Year: 2003

Performer: Norah Jones

Writer: Dolly Parton

Appears on: Just Because I’m A Woman

“The Grass is Blue” is from Dolly Parton’s thirty-fifth, album, a collection of bluegrass songs with the same title. Parton’s underrated songwriting talents are perfectly harnassed by Norah Jones in her amazing cover. The heartbreaking song reflects the state of mind of a party to a recently ended relationship, where her only survival strategy is to tell herself the opposite of reality. If you’ve never heard this, you’ll be blown away.

#43: “Fake Plastic Trees”

Year: 1995

Performer: Radiohead

Writer: Radiohead

Appears on: The Bends

“Fake Plastic Trees” reflected Radiohead and Thom Yorke’s dissatisfaction with the artificiality of the modern world. The song was inspired by a real plan in a British community to use fake trees rather than real ones because they would be cheaper to maintain. Those fake trees act as a metaphor for the fakeness in our lives and relationships that will never be able to satisfy us.

The band struggled recording the song until finding inspiration after attending a Jeff Buckley concert.

#42: “Inner City Blues”

Year: 1971

Performer: Marvin Gaye

Writer: Marvin Gaye

Appears on: What’s Going On?

From beginning to end, Marvin Gaye’s 1971 album What’s Going On? is a revelation that has never let go of its grip on popular music. “Inner City Blues” reflects the increasingly challenging plight of inner-city African Americans who had become isolated and trapped. Among the songs complaints are that the US can send a man to the moon, but not take care of its own. Sadly, the poignancy of the song continues to be topical.

#41: “All Things Must Pass”

Year: 1970

Performer: George Harrison

Writer: George Harrison

Appears on: All Things Must Pass

If Dolly Parton is not the world’s most underrated songwriter, then perhaps George Harrison is. Despite the fame he achieved as a Beatle, he was never able to escape the shadows of John Lennon and Paul McCartney.

“All Things Must Pass” was written while Harrison was still a Beatle, but the song became the title track to his first solo release in 1970. The lyrics are deeply informed by Timothy Leary’s translation of a Lao Tzu poem. The song perfectly encapsulates what Abraham Lincoln called the wisest expression of all time: “This too shall pass.”

#40: “I Cover the Waterfront”

Year: 1944

Performer: Billie Holiday

Writer: Johnny Green and Edward Heyman

Appears on: Lady Day: The Complete Billie Holiday on Columbia – 1933 to 1944

Billie Holiday’s cover of the beautiful 1933 song “I Cover the Waterfront” is among her most haunting. The song contains such devastating lines as:

“I cover the waterfront
I’m watching the sea
Will the one I love
Be coming back to me?

I cover the waterfront
In search of my love
An I’m covered
By a starlit sky above”

#39: “Hellhound on My Trail”

Year: 1937

Performer: Robert Johnson

Writer: Robert Johnson

Appears on: The Complete Recordings

“Hellhound on my Trail” is a common phrase in blues songs signifying the stalking approach of evil. The image of the hounds of hell coming to take sinners was also prevalent at the time. Perhaps literally, the hounds are society closing in on a black man trying to survive Jim Crow. If so, the song has a shocking depth to it as a description of a man losing a war both internally and externally.

It’s not hard to understand why some view this as the best blues song of all time.

#38: “Peace on Earth”

Year: 2000

Performer: U2

Writer: U2

Appears on: All That You Can’t Leave Behind

Just when it looked like Ireland was on the cusp of putting a century of bloodshed behind it, a bomb went off in the city of Omagh in the busy part of the afternoon. It killed 29 people and injured 220 others. Since the bomb exploded at about 3 pm on a nice day, school children were among those who paid the ulitmate price. A splinter group of the IRA, called the Real IRA, was responsible after being dissatisfied with the IRA’s negotiations with England.

This may be U2’s most powerful song. The lyrics list the names of children who died (“they’re reading names out over the radio, all the folks the rest of us won’t get to know, Sean and Breeda, Gareth, Anne, and Rita, aren’t those lives bigger than some guys big idea?”)

#37: “Bohemian Rhapsody”

Year: 1975

Performer: Queen

Writer: Freddie Mercury

Appears on: A Night at the Opera

Wayne’s World took this classic and made the ultimate car ride sing along. Nothing like “Bohemian Rhapsody” had existed before and from seven years before MTV the music video for the song is still famous. It seems that no one yet has been able to crack the code of the lyrics, should there actually be one, but they do seem to be intensely personal for Freddie Mercury.

#36: “Across the Universe”

Year: 1970

Performer: The Beatles

Writer: John Lennon and Paul McCartney

Appears on: Let It Be

Had John Lennon been able to sleep one evening, we may never had gotten this song which he composed at 3 am on a piano. Lennon rightfully considered this song, partially inspired by his dabblings in transcendental meditation, to be among his best.

#35: “Changes”

Year: 1971

Performer: David Bowie

Writer: David Bowie

Appears on: Hunky Dory

“Pretty soon now you’re going to be older,” may be the most acerbic description of the human condition ever put to paper. It’s also the battle that rock ‘n roll musicians have been waging since their origin – a search for some elixir from keeping them from becoming stale and irrelevant. Bowie astutley sings that the only around this is through constant reinvention.

#34: “American Tune”

Year: 1975

Performer: Paul Simon

Writer: Paul Simon

Appears on: There Goes Rhymin’ Simon

“American Tune” was written by Paul Simon in the age of Vietnam protests and a decline in the confidence of American institutions because of epsisodes such as Watergate. The song describes the experience of immigrants and their failure to achieve the American dream.

Ironically, the tune for “American Tune” is based upon a Bach composition, perhaps intentionally suggesting that the basis for America is the borrowing and amalagating of multitudes of culture and then often letting those down from whom it was borrowed from.

#33: “One For My Baby”

Year: 1958

Performer: Frank Sinatra

Writer: Harold Arlen and Johnny Mercer

Appears on: Frank Sinatra Sings For Only The Lonely

Harold Arlen was a monumental songwriter. He wrote the melody to the songs featured in The Wizard of Oz (including “Over the Rainbow”) and “I’ve Got the World on a String.” Frank Sinatra made the definitive version of this saloon song. It appeared on the album Frank Sinatra Sings For Only the Lonely, a phenomenal concept album about loneliness that will never fail to blow you away at three o’clock in the morning.

#32: “River”

Year: 1971

Performer: Joni Mitchell

Writer: Joni Mitchell

Appears on: Blue

Shortly after breaking up with Graham Nash, Joni Mitchell traveled to Europe and wrote most of the songs that appeared on Blue, one of the most depressingly pleasant records ever made.

“River” has become an unlikely seasonal favorite and one of the most covered songs from Mitchell’s catalog. Little interpretive skills are needed to understand the song: the singer feels fully responsible for a break-up and is desperately searching for a way to escape the pain. It’s likely, as some have suggested, that the scenes she describes in the song are memories of her childhood in Canada where Christmas must have been a very different kind of celebration than in California or Greek islands. Ultimately, the frozen River that doesn’t exist is a path backwards to a simpler time.

#31: “Acknowledgement”

Year: 1965

Performer: John Coltrane

Writer: John Coltrane

Appears on: A Love Supreme

Excepting Kind of Blue, A Love Supreme is probably the most storied jazz record ever recorded. Kind of Blue was a record that John Coltrane played on as part of Miles Davis’ sextet about six years before this record was recorded. But, Coltrane had at one time been fired by Davis because of his heroin addiction. As he matured, Coltrane increasingly turned inward and spiritual and composed his magnum opus at his Long Island home.

Coltrane tragically died at the young age of 40 in 1967 from liver cancer. He was one of many jazz greats to die young from liver ailments, potentially a result of contracting hepatitis from sharing needles before the illness was widely recognized.

#30: “This Land is Your Land”

Year: 1940

Performer: Woody Guthrie

Writer: Woody Guthrie

Appears on: The Best of Woody Guthrie

“This Land is Your Land” shares with “Imagine” the distinction of being a song many love, and yet the clear meaning repeatedly flies over their heads. “This Land is Your Land” is no patriotic anthem and was a direct reaction to Woody Guthrie hearing the genuinely patriotic song “God Bless America.” In Guthrie’s America, this land may be made for you and me, but it inures to the benefit of a tiny elite. As time has passed, many of the songs original, edited lyrics have received the light of day, including verses such as:

“One bright sunny morning in the shadow of the steeple,
by the relief office I saw my people.
As they stood hungry,
I stood there wondering if God blessed America for me.”

The melody to the song was taken from The Carter Family’s “When the World’s On Fire.”

#29: “Vincent”

Year: 1971

Performer: Don McLean

Writer: Don McLean

Appears on: American Pie

For many years the story of Vincent Van Gogh’s suicide has been told, but recently scholars have opened up the possibility that Van Gogh might not have committed suicide after all. Whether he did or not has no impact on the resonance of this Don McLean composition, though. The song explores the line between “crazy” and “genius” and how fine a line it can be. While many continue to think of Van Gogh as the crazy painter that cut off his ear and killed himself, McLean perfectly captures the reality that Van Gogh wasn’t crazy at all, just capable of seeing things everyone else missed.

#28: “Smells Like Teen Spirit”

Year: 1991

Performer: Nirvana

Writer: Kurt Cobain

Appears on: Nevermind

“Smells Like Teen Spirit” is one of those rare songs that really did change everything. The alternating softer versus and hard chorus set the template for the “Nirvana” sound, the wardrobe made thrift stores popular, and grunge music was brought into the mainstream.

The song seems to be about the social structure of high school and the strange things people do to fit in – losing themselves in the process. The title famously was taken from the deodorant that a girlfriend of Cobain’s wore. After spending time together, a friend wrote “Kurt smells like teen spirit” in order to joke about the fact the two had been together.

The line, “oh well, whatever, nevermind…” seemed to sum up the lost Generation X.

#27: “Jolene”

Year: 1975

Performer: Dolly Parton

Writer: Dolly Parton

Appears on: Jolene

When you run through the best songwriters in your head, you may skip over Dolly Parton. You shouldn’t. “I Will Always Love You,” “Coat of Many Colors,” “9 to 5,” “Light of a Clear Blue Morning,” and “The Grass Is Blue” are all evidence of a woman who has mastered the craft. It is likely that “Jolene” will be the song she is most remembered for – a remarkable achievement in which Parton is able to write an empowering song about her own insecurities. Now, that’s tough to do.

#26: “A Whiter Shade of Pale”

Year: 1967

Performer: Procol Harum

Writer: Gary Booker, Keith Reid, and Matthew Fisher

Appears on: Procol Harum

There is probably not much point in trying to define “A Whiter Shade of Pale” in any kind of literal way. Besides, the mystery in the song is perhaps its greatest quality. The organ part inspired by classical music, a vocal to rival soul music, and lyrics that herald from the “summer of love” all combine to produce a record that is quite literally impossible to forget.

#25: “Desolation Row”

Year: 1965

Performer: Bob Dylan

Writer: Bob Dylan

Appears on: Highway 61 Revisited

“Desolation Row” has its origin in a post card made depicting a lynching, in similar fashion to “Strange Fruit.” This lynching happened in 1920 in Dylan’s hometown of Duluth, Minnesota. Black circus workers were accused of raping a 19 year old girl. Based upon the evidence, it’s likely this rape never occurred, but that didn’t matter to the mob and they retrieved the workers from jail, beat and then finally lynched them.

Most think that the title of the song is an amalgamation of the titles of two novels: Desolation Angels by Jack Kerouac and Cannery Row by John Steinbeck. Desolation Angels is a largely true account of the coming of age of the Beat Poets, particularly Kerouac himself, as he realizes the fundamental solitude of his life. “A peaceful sorrow at home is the best I’ll ever be able to offer the world, in the end, and so I told my Desolation Angels goodbye. A new life for me,” is how Kerouac concludes the novel. The “Desolation Angels” were the myriad of fellow poets and authors that Kerouac had once, but no longer, connected to.

Dylan drops the not-so-subtle hint of where the characters in his song come from when he says, “Yes, these people that you mention, I know them they’re quite lame. I had to rearrange their faces and give them all another name.” This is a world where brutal murders happen because of skin color and where compassion and understanding have evaporated. In the end, Dylan gives up his “Desolation Angels” too in order to push his art further into directions no one else had cared to go.


#24: “Unchained Melody”

Year: 1965

Performer: The Righteous Brothers

Writer: Alex North and Hy Zaret

Appears on: Just Once in my Life

Ever since its inclusion in the 1990 film Ghost, “Unchained Melody” has been connected to that movie. But the origins of the song lie in a different movie, Unchained, which is where the title of the song comes from. The movie is a prison movie where an inmate has to decide between escaping and serving out his sentence and being with the woman he misses once again.

This song almost personifies the word “classic” and it’s tailor made for The Righteous Brothers.

#23: “Layla”

Year: 1970

Performer: Derek & the Dominoes

Writer: Eric Clapton and Jim Gordon

Appears on: Layla and Other Assorted Love Songs

There’s no mystery at all who this song is about. Eric Clapton fell madly in love with Patti Boyd, the wife of his friend and Beatles’ guitarist George Harrison. All things being equal, Harrison was pretty cool about it and stayed friends with Clapton. (While being interviewed once, a reporter stumbled about trying to define the relationship between Clapton and Harrison until Harrison interrupted and said simply, “We shared a wife.”)

The song features one of the all time great riffs and lyrics about tormented and unrequited love inspired by blues classics.

#22: “Martha:

Year: 1973

Performer: Tom Waits

Writer: Tom Waits

Appears on: Closing Time

The fact that Tom Waits seems to hate the entire Closing Time album has always seemed odd. Perhaps it is a little like seeing old pictures of yourself and recoiling. The record was not immediately popular, but it became a gold mine for singers looking for material. Waits versions were far superior to any covers, though, with his cool blend of jazz and folk.

“Martha” is a charming song of an allowance to consider what could have been that just may make you cry. It is said the the song was the quasi-inspiration for the Adele song “Hello.”

#21: “Heart Shaped Box”

Year: 1993

Performer: Nirvan

Writer: Kurt Cobain

Appears on: In Utero

“Heart Shaped Box” was the culmination and perfection of the ‘Nirvana sound’ of alternating soft and slower versus with hard, loud, and fast choruses.

The lyrics are some of Cobain’s best, with lines such as “I wish I could eat your cancer when you turn black” and “Hey! Wait! I’ve got a new complaint.” The song seems to be about the ups and downs of Cobain’s marriage with Courtney Love, which had become both an outlet and an unhealthy codependency.

The music video to the song, direct by Anton Corbijn, is one of the best ever.

#20: “Gimme Shelter”

Year: 1969

Performer: The Rolling Stones

Writer: Mick Jagger and Keith Richards

Appears on: Let it Bleed

In many lists “(I Can’t Get No) Satisfaction” is listed as The Rolling Stones greatest song. Don’t be fooled. “Gimme Shelter” is and it’s not even close. It’s also one of those songs that you can hear a million times and never actually understand what the words to the song are unless you sit down and read the lyrics. The song was inspired by the Vietnam War as well as the increasingly vocal reactions to it in the West. It’s a plea, not for peace and understanding, but for just a little sanity amidst the terror. Is that really so much to ask for?

#19: “Thunder Road”

Year: 1975

Performer: Bruce Springsteen

Writer: Bruce Springsteen

Appears on: Born to Run

There is an immediacy, almost a kind of panic, in “Thunder Road” from a kid who knows his life isn’t about to be over, but he’s on the cusp of decisions that will be determinative in how that life evolves. One of the more fascinating aspects of the song is that being written from the perspective of the male narrator, listeners are left to wonder who “Mary” is, what she wants, and what kind of life she is preparing herself. You’re tempted to conclude after hearing this song many times that perhaps the singer is attempting to rescue a woman who has no interest in being rescued. (A common male shortcoming.) But, the song is a lot more fun to listen to if you just imagine two people driving off for adventure at the end of it.

#18: “I Know it’s Over”

Year: 1986

Performer: The Smiths

Writer: Morrissey and Johnny Marr

Appears on: The Queen is Dead

The Queen is Dead is certainly a contender for best album of the 1980s and its’ one of the very few albums that gets better and better as time passes. “I Know It’s Over” is its most devastating and haunting piece, containing the perhaps suicidal laments of a broken heart. Morrissey’s voice communicates the austere images in a perfect forlorn cry.

#17: “Redemption Song”


Performer: Bob Marley

Writer: Bob Marley

Appears on: Legend

“Redemption” literally means to buy back and Marley’s song refers to the efforts required of African descendants throughout the world to buy back their intellectual freedom. The song was inspired by a speech given by pan-Aftican proponent Marcus Garvey about the need to fully develop one’s mental powers if one is not to live as a serf or slave in this world. Speaking in Nova Scotia in 1938, Garvey said, “When God made you He made you the masters of the world, not serfs and slaves, but your mind must be developed intelligently. It is your mind that rules the body.”

No matter your background, it’s hard to not find truth and beauty in Marley’s song.

#16: “Old Friends / Bookends Theme”

Year: 1968

Perfomer: Simon & Garfunkel

Writer: Paul Simon

Appears on: Bookends

Sooner or later we all have to come terms with our eventual deaths. Punning the term “old friends,” this song details the conversation between two long-time friends whose time is coming to an end. It climaxes the very interesting concept album of Bookends, which sought to move through the song cycle like a literary work that captures the important aspects of a human life.

“Bookends Theme” is presumably poetry describing the very end of life. And what poetry it is. Few songs create the immediate pathos from its’ lines:

“A time it was

And what a time it was, it was

A time of innocence

A time of confidences

Long ago it must be

I have a photograph

Preserve your memories

They’re all that’s left you”

#15: “Be My Baby”

Year: 1963

Performer: The Ronettes

Writer: Jeff Barry, Ellie Greenwich, and Phil Spector

Appears on: Be My Baby: The Very Best of the Ronettes

It’s hard to believe that the career of Phil Spector would ultimately end by a murder conviction in 2009. He still has a minimum of eleven more years of his sentence to serve. Forty-six years before the conviction Spector was changing the face of popular music through his lush and dense productions labeled the “wall of sound.”

This was far and away Brian Wilson’s favorite song, causing an obsession within him to duplicate the sound and shift his writing and production talents.

An interesting piece of trivia: Cher performed backing vocals on the record, the first time she was ever recorded.

#14: “Who Knows Where the Time Goes”

Year: 1970

Performer: Nina Simone

Writer: Sandy Denny

Appears on: The Essential Nina Simone

Sandy Denny’s series of rhetorical questions are indicative of a person fascinated, almost to the point of being haunted, by the unexplainable aspects of nature and the universe. How do the birds know its time fly south? How does the sun know how to set? The singer finally settles upon a philosophy of enjoying her whimsy despite not being able to explain it.

Nina Simone records a gorgeous version of this song before a live audience. Within the strength of her voice, it’s a little bit easier (although still hard) to let go of the past.

#13: “All Along the Watchtower”

Year: 1968

Perfomer: Jimi Hendrix

Writer: Bob Dylan

Appears on: Experience Hendrix

The 21st Chapter of Isaiah is filled with denunciatory prophecy regarding the fall of Babylon. The message was given prior to the Jewish nation being led into captivity to Babylon, making the prophecy one of a future deliverance based upon a promise by God. This song seems to dwell particularly on verses 5-9 of that chapter: ”

Prepare the table, watch in the watchtower, eat, drink: arise, ye princes, and anoint the shield.

For thus hath the Lord said unto me, Go, set a watchman, let him declare what he seeth.

And he saw a chariot with a couple of horsemen, a chariot of asses, and a chariot of camels; and he hearkened diligently with much heed:

And he cried, A lion: My lord, I stand continually upon the watchtower in the daytime, and I am set in my ward whole nights:

And, behold, here cometh a chariot of men, with a couple of horsemen. And he answered and said, Babylon is fallen, is fallen; and all the graven images of her gods he hath broken unto the ground.

What modern meaning did Dylan intend? Your guess is as good as ours. But, we think the comparison being drawn is that both in the ancient nation of Israel and the modern world, most people are consumed in the day to day and live devoid of purpose despite larger and more important themes looming in the background.

The apocalyptic overtones were a perfect match for Hendrix’s chaotic beauty on guitar and to this day it is Hendrix’s arrangement that Dylan plays in concert.

#12: “I Think It’s Going to Rain Today”

Year: 1968

Performer: Randy Newman

Writer: Randy Newman

Appears on: Randy Newman

Randy Newman has written a slew of intellectual, sophisticated, deep, and humorous songs. Among them have been “Sail Away,” in which a slave trader tries to convince a slave to come with him to “Charleston bay,” and “God’s Song,” where God looks down in mockery at the loyalty of human beings. He’s also had a successful career contributing to film soundtracks, notably Toy Story.

But, “I Think It’s Going to Rain Today” is the best song he’s ever written. The best interpretation of the song we can come up with is that it’s sung by a man unable to connect to himself and understand his underlying emotions. Despite help being available everywhere he turns, he’s not able to take advantage of it.

Norah Jones does a wonderful cover of this song.

#11: “Mystery Train”

Year: 1955

Performer: Elvis Presley

Writer: Junior Parker

Appears on: The Essential Elvis Presley

Before becoming a sensation with RCA Victor, Presley spent two years with Sam Phillips’ Sun Records enjoying a modicum of regional success. The irony is that the music he made before he ever became famous invariably exceeds in quality anything he made afterward. “Mystery Train” was the last single Presley released at Sun in late 1955. (“Heartbreak Hotel” would be his first RCA release in 1956.) The song was written and originally recorded by Junior Parker, another Sun recording artist. The sound that Elvis had been creating in Memphis along with Scotty Moore and Bill Black had been perfected by the time this song was recorded, with unmistakeable Scotty Moore riffs to accompany an unmistakeable and confident voice.

The song most definitely has its roots in the traditional “Worried Man Blues” performed by The Carter Family, Woody Guthrie, and Cisco Houston among others. That song included the lines, “The train arrived sixteen coaches long.” In that song, the listener feels as though the singer wants to be taken away on that train to escape his life. But, in the Presley rock-n-roll update of the Junior Walker song, the listener feels that the singer wants to be taken on that train if only to escape the boredom of where he is.

#10: “Love in Vain Blues”

Year: 1937

Performer: Robert Johnson

Writer: Robert Johnson

Appears on: The Complete Recordings

The book of Ecclesiastes begins with the words: “Vanity of vanities, all is vanity.” As Johnson makes painfully clear in the song, “all” includes the love he has to give. No matter how strongly he feels it, the train still pulls away from him. Explaining the power of Robert Johnson’s music or the unparalleled influence he has had on rock-n-roll is a very difficult thing to do. His entire life is shrouded in myth and legend, only adding to his appeal and mysteriousness. But, fundamentally Johnson was able to combine innovations in guitar playing (including playing chords in a manner much more similar to the piano) with lyrics that distilled the very essence of the delta blues.

It’s extremely sobering to contemplate the fact that there was every chance in the world that Robert Johnson might never have been recorded before he died. How many others with perhaps comparable talent did we lose before ever realizing that they lived?

#9: “A Change Is Gonna Come”

Year: 1964

Performer: Sam Cooke

Writer: Sam Cooke

Appears on: 30 Greatest Hits: Portrait of a Legend

Sam Cooke may have done more to create soul music than any other artist. He also took an active role in the business side of his career and by 1963 had grown quite wealthy. But, that didn’t prevent a clerk at a Holiday Inn in Louisiana from denying admission to Cooke and his band because the hotel was not integrated. After causing commotion in the hotel, Cooke was arrested for disturbing the peace. The incident was the spark that inspired him to write this gorgeous and hopeful song that became an anthem and was prominently featured at the ending of the Spike Lee film Malcolm X.

Cooke sadly died the following year under suspicious circumstances. The official version of events has Cooke taking a woman back to a hotel who leaves while he’s in the restroom. When Cooke runs out to the hotel clerk she believes she is in danger and shoots in self-defense. While no one can say for certain what really happened, it’s unlikely events unfolded the way either the hotel clerk, Bertha Franklin, or the girl, Elisa Boyer said they did. Most likely Cooke was the victim of a robbery and was killed after he began unraveling the situation. In any event, it was a sad end to a man whose talent was undeniable and who was only 33 years old.

#8: “God Only Knows”

Year: 1966

Perfomer: The Beach Boys

Writer: Brian Wilson and Tony Asher

Appears on: Pet Sounds

Many people were first introduced to this song from its inclusion in the film Love Actually, but years before it was the cornerstone to Pet Sounds, one of the finest albums in rock music history.

“God only knows” is a pretty common English idiom for when something is virtually unknowable. Ironically, it is not proper English and often gives non-native speakers a difficult time with its interpretation. The correct phrase should be “Only God knows” which would mean that an omniscient power was the only entity that knows that information. “God only knows” technically means that “God” can only “know” and cannot experience other qualities.

The song by The Beach Boys loads as much sentiment and experience into the phrase as anyone could possibly imagine. Of course, you could interpret the phrase that titles the song as the singer simply expressing that he doesn’t know what he would be without his love. But the meaning is also clearly literal. He cannot possibly live without her and will love her until he dies, at which point only God knows what plans lie in store for him.

No one had ever combined spiritual thought with love songs before Wilson and Asher. The profound lyrics coalescing with an unbelievable baseline, angelic strings, and Carl Wilson’s voice makes for a song that never gets tiring.

#7: “I’m So Lonesome I Could Cry”

Year: 1949

Performer: Hank Williams

Writer: Hank Williams

Appears on: 20 of Hank Williams’ Greatest Hits

Everyone has heard the jokes about country music (What do you get when you play a country song backward? Your dog, truck, and wife back). But this may have been the song that cemented country’s reputation for being the music of down-on-your-luck men. Elvis Presley called it the saddest song he’s ever heard. Bob Dylan was also captivated by the song and can be seen playing it in the documentary Don’t Look Back.

When the lyrics are read, you sometimes forget that you are not reading John Keats even though the poetry may not be far from his level of writing. Quite simply, the song is the greatest expression of clinical depression that’s ever been made. The stories are of a man who is reminded of sadness by everything he sees. (“The moon just went behind the clouds to hide its face and cry” and “The silence of a falling star lights up a purple sky, and as I wonder where you are I’m so lonesome I could cry.”)

Four years after he wrote “I’m So Lonesome I Could Cry” Hank Williams was dead, a victim of alcoholism and prescription drug addiction.

#6: “Strange Fruit”

Year: 1939

Performer: Billie Holiday

Writer: Abel Meeropol

Appears on: Lady Day: The Complete Billie Holiday on Columbia – 1933 to 1944

Once the Civil Rights movement took hold, it’s strength very well may have been in the respect it showed for the people it tried to persuade. At the heart of the movement was raising awareness for what was really taking place and relying on the innate goodness and morality in most people to not let it continue. The lyrics to “Strange Fruit” seem to have the power to change hearts and minds from a single reading. Decades after its composition it has lost none of its power.

The story of the song began when a Jewish English teacher from the Bronx, Abe Meeropol, saw a picture of a lynching on a postcard and could not forget the image he saw. That lynching was of Thomas Shipp and Abe Smith in Indiana during 1930 (the picture is below). He eventually put music to the song (which included such horrific lines as “The bulging eyes and the twisted mouth”) and played it for a New York City club owner who brought the song to the attention of Billie Holiday. She performed the song for the first time at the only integrated nightclub and New York City in 1939 and it soon became a nightly ritual.

Some years later Abe Meeropol and his wife would adopt the children of Ethel and Julius Rosenberg following their execution.

Image result for lynching

#5: “In My Life”

Year: 1965

Performer: The Beatles

Writer: John Lennon and Paul McCartney

Appears on: Rubber Soul

During the years between 1963 and 1969, the Beatles recorded more than 200 songs and you have probably heard every one of them at one point or another. Which song was their greatest? Ask the question and you’ll get plenty of answers, but we’re happy to nominate “In My Life” for that honor.

A beautiful and sentimental song, “In My Life” was birthed while John Lennon rode on a bus through the neighborhoods he remembered from his youth. In a rare case of authorship dispute between Lennon and McCartney (the only other song in which there was substantial dispute was “Elanor Rigby”) Lennon remembers having the song nearly finished before McCartney heard it while McCartney remembers seeing the song after only the first verse was completed and he claims significant lyrical contributions as well as authorship of the melody. The specifics hardly matter today.

The song as well as the album it appeared on marked a watershed moment for the group. It is hard to listen to this and realize that only about a year before they were the four moptops from Liverpool. On “In My Life” those four moptops showed they had grown up quite a bit.

#4: “Over the Rainbow”

Year: 1939

Performer: Judy Garland

Writer: Harold Arlen and E.Y. Harburg

Appears On: The Judy Garland Collection

The greatest musical moment in film was almost cut – executives at MGM thought that the song did nothing more than slow down the story of Dorothy. The song is now one of the most recognizable musical pieces on earth, perhaps as well known as “Happy Birthday” and “Mary Had a Little Lamb.”

Perhaps understanding the essence of “Over the Rainbow” comes from the relationship that singers have had to the song. It was clearly always the song that Judy Garland was most closely identified with and she regularly performed it in the decades after The Wizard of Oz was made. She never really made it to a place where bluebirds fly during her life and died young from a barbiturate overdose.

Of the many cover versions that would be made, we think Eva Cassidy’s was the best. Her interpretations of jazz songs and standards were never widely known before she died of cancer at 33, but after her death, she enjoyed tremendous popularity in the UK. This performance from the Blues Alley in Georgetown is well worth watching.

#3: “Imagine”

Year: 1971

Performer: John Lennon

Writer: John Lennon

Appears On: Imagine

In retrospect it’s somewhat incredible that John Lennon’s (mostly) Marxist anthem became so easily accepted and well-known. Ironically, the reason it was is probably because this song is what people want it to be rather than what it really is.

What it is is a song that reminds us that many of the things we cling most closely to are also the things that divide us and that rather than waiting for a God to resolve our problems, those problems will be with us until we decide to solve  them ourselves. The song was inspired by the poetry of Yoko Ono as well a present from comedian and civil rights activist Dick Gregory.

Today, “Imagine” remains the closest thing the world has to a secular prayer.

#2: “Visions of Johanna”

Year: 1966

Performer: Bob Dylan

Writer: Bob Dylan

Appears On: Blonde on Blonde


This is the greatest song written by the greatest songwriter of all time. Ostensibly, it tells the story of the singer’s time with Louise, who is a perfectly good companion but not good enough for the singer to overcome his constant visions of his true love Johanna. People have ruined themselves by reading too much into Dylan’s songs, but you would have to be pretty dense to not see parallel meanings in this one. The 24 year old Dylan was beginning to realize that no matter how many perfect songs he wrote he could not achieve immortality through his art as he perhaps once believed, because even if people were still listening to the music in 500 years, he would still be dead. The feeling of being lost at midnight pervades the song and leads up to the greatest line in popular music history, “Inside the museums infinity goes up on trial. Voices echo, ‘this is what salvation must be like after awhile.'”

Louise is a German name meaning “to struggle”, while Johanna is a Hebrew name meaning “God’s grace.”

The clip above is from the fantastic documentary No Direction Home and features a live performance from 1966.

#1: “Hallelujah”

Year: 1995

Performer: Jeff Buckley

Writer: Leonard Cohen

Appears On: Grace

Excepting Bob Dylan, a case can be made that Leonard Cohen was the greatest songwriter of the last half of the twentieth century. A combination of that talent with the unbelievably beautiful voice of Jeff Buckley makes for the greatest song of all time.

Cohen spent years writing the song before recording it for his 1984 album Various Positions. Then the song was almost forgotten until Velvet Underground founder John Cale took an interest and asked Cohen for a copy of the lyrics. Cohen returned the lyrics to the version he recorded as well as several verses that were edited out. Cale rearranged the lyrics to the song and recorded it on a Cohen tribute record in 1991. Jeff Buckley, who was performing at the East Village club Sine, covered Cale’s version and ultimately included it on his haunting debut album Grace. Following Buckley’s definitive performance the song became a classic covered by k.d. lang and performed at the 2010 Winter Olympics as well as a Rufus Wainwright cover included on the Shrek soundtrack.

“Hallel”’s  are Jewish songs of praise taken from Psalm 113-118 that marked the joyful moments of life, while “Jah” is an abbreviated form of the name of God. It is certainly over-covered and performed to death, making its tremendous power harder to spot. But Cohen’s crying recognition that submission to the divine is necessary in both moments of joy and despair has inserted itself into the collective subconscious of the world to such an extent it’s unlikely to ever be dislodged.


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