10 of the Saddest Songs in Music

Music is one of the few things that can instantly bypass traditional divides. Whether it’s the stadium metal style of Guns N’ Roses, the perky pop of Taylor Swift or the evocative art rock of Arcade Fire, music has the uncanny ability to instantly break down the borders that can sometimes seem so rigidly implacable in life.

“There is no feeling, except the extremes of fear and grief, that does not find relief in music”, said George Eliot of its innate power. In and through music, we have the ability to access emotions that otherwise might remain hidden or unknown, and nowhere are those feelings more accessible than with a song that tugs, most particularly, at the heartstrings. While some sad songs have served as a political statement, forcing us into a slow burn with the use of a simple chord, some drums and one really good line, there are also those that have channeled our most complex emotions and given us a passageway again to the part of ourselves that was left behind for the sake of life among the maddening crowd.

While Strange Fruit simmers as Billie Holiday relays the injustices perpetrated in America’s south, Jeff Buckley’s cover of Hallelujah teems with the desperation, and disappointment, of love. There may be no definitive marker for what makes a song truly sad, but the following can’t help but leave the listener a little speechless for the penetrating truth they rankle with or the hope that seems almost entirely lost.

10  10. Creep – Radiohead

A song off Radiohead’s first album, Pablo Honey, that was released long before the band had earned its stripes, Creep is a bit more morose than many Radiohead songs but still has the same eerie, apart feeling of many of their best tunes. Purportedly written about a girl that singer Thom Yorke had known in University, Creep gives the listener an immediate sense of alienation that is further enforced by Yorke’s disheartening assertion of, “I wish I was special/But I’m a creep”. Though the song was not popular upon its initial release, it has been covered by artists as divergent as Prince and The Pretenders since its reissue in 1993.

9 Weeping Willow – The Verve

While the song Weeping Willow certainly wasn't the most well known tune off of The Verve’s 1997 breakthrough album Urban Hymns, it is among the most stunningly poignant on an album that is full of veritable heart-churners. Beginning with a down stroke, the song gives way to a beautiful but morose froth of noise that is punctuated by Ashcroft’s wise, and world-weary, lyrics. It’s unlikely that a tune called Weeping Willow is readied to be a dance club hit, but when Ashcroft sings, “Weeping willow/The pills under my pillow”, it’s hard to quell the internal ache.

8 Imagine – John Lennon

One of the classic ballads in the history of music and John Lennon’s most famous song, Imagine was released in 1971 and inspired by a poem in wife Yoko Ono’s 1964 book Grapefruit. Ranked as number 3 on Rolling Stone magazine’s “The 500 Greatest Songs of All Time”, the song elegantly broached the idea of attaining world peace through the purposeful breakdown of the economic, religious and ethnic barriers that separated people.  While the lilt of the piano and Lennon’s unassuming voice sound hopeful enough, the song incenses with a vision that is still far from realization.

7 Hallelujah – Jeff Buckley

A Leonard Cohen cover off of Buckley’s 1994 album Grace, Hallelujah dramatically fueled Buckley’s popularity and ensured that his father Tim Buckley was not the only member of the family to enter the annals of music. Starting with a flustered breath and sparse guitar before his four-octave voice appears sounding half hushed and partially hopeful, it all breaks apart beautifully when he sings, “Love is not a victory march/It’s a cold and it’s a broken Hallelujah.” While Buckley passed away in 1997 at the age of 30, the musical legacy he left behind has far surpassed his modest output.

6 The Eternal – Joy Division

A song off the Manchester band’s final album Closer, the intense, almost apocalyptic sound that inspired a host of post-punk bands and characterizes many of the Joy Division’s songs is partially lost here, slowed down and beat out.  The Eternal features the cold, slow lilt of a synthesizer that warbles in the background, the music falling downward as lead singer Ian Curtis emotes most soberly, “Try to cry out in the heat of the moment/Possessed by a fury that burns from inside.” While the band was known for the seeming claustrophobia of its music and Curtis’s stately but solemn lyrics, The Eternal seems like an ode to a life that is over, as the narrator stands hovering above the wreck.

5 One – U2

Though a song called One might seem to allude to the unity of all things, the third single off U2’s 1991 Achtung Baby was written at a pivotal time in the band’s career. As they disputed their sound and their future together while recording in Berlin, Germany, guitarist The Edge happened upon a chord progression that would become the song One. With lyrics written by Bono that talked about the band’s frayed relationships and the recent fall of the Berlin Wall, the song served as an emotional tribute to the healing power of love and worked to re-unify U2. Considered among the band’s best songs, One has also inspired the name of the charitable organization ONE Campaign for which Bono is a spokesperson.

4 Tears In Heaven – Eric Clapton

Written by Eric Clapton and Will Jennings and released in 1992, Tears In Heaven was a tragic tribute to Clapton’s late son in the form of a heartfelt ballad. After experiencing the death of his manager, two of his roadies and his 4-year-old son Conor, who had accidentally fallen from an open apartment window, Tears in Heaven served as a therapeutic means for Clapton to deal with the seemingly insurmountable losses. Though Clapton’s capacity for turning his grief into music made the song one of his most popular, it also served as a poignant memoir of grief and highlighted the necessity to transcend.

3 Twilight – Elliott Smith

A song off Smith’s unfinished and final album From a Basement on a Hill that was released on October 19, 2004, Twilight is a spare and intensely moving song, particularly so in light of Smith’s suicide in 2003 at the age of 34. Utilizing a simple chord progression and featuring his earnest, melancholy voice, the beauty and nostalgia of the song comes through with the strings, as if to alert the listener to a twilight that may not come. Though Smith wasn't around to make the final decisions on the album, From a Basement on a Hill contained some of his most touching songs and peaked higher than any of his previous albums at 19 on the US Billboard 200.

2 All Apologies – Nirvana

Released as a single off of Nirvana’s third album In Utero, All Apologies is one of the more compellingly understated songs in the recent catalog of rock music and one of Nirvana’s finest moments. Initially recorded in 1991, singer Kurt Cobain wrote the song as a peaceful tribute to his wife Courtney Love and their daughter Frances Bean. While the song is stunning on the surface, there’s a dreadful potency to the idea of apology when Cobain sings, “What else should I be/All apologies”, given his early suicide in 1994 at 27 years of age.

1 Strange Fruit – Billie Holiday

Though Strange Fruit initially started out as a song Billie Holiday sang during her live performances, it was after it was recorded in 1939 that it found an audience and received wide acclaim. Written by songwriter Abel Meeropol, Strange Fruit sounds tempting enough but refers quite darkly to the lynching of black people that was a familiar sight in the Southern United States.  Though Holiday’s version is striking and rendered with subtlety, you can feel the true horror of the subject when she unmercifully sings, “Black bodies swinging in the Southern breeze/Strange fruit hanging from the Poplar trees.”

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