EW's 50 Most Heartbreaking Songs of All Time

Last month, EW's Jason Adams put up a post on the Music Mix asking "What's the most heartbreaking song of all time?" and naming Smog's "Cold Blooded Old Times" as his top pick. Nearly 2,000 comments later, we realized we'd touched a (really depressed) nerve. So we sat down to create a list of our own favorites, available below in reverse order, No. 50 to No.

50. Wham!, "Careless Whisper" (1984)
49. Sufjan Stevens, "John Wayne Gacy Jr" (2005)
48. Meshell Ndegeocello, "Bitter" (1999)
47. Skeeter Davis, "The End of the World" (1962)
46. Lauryn Hill, "Ex-Factor" (1998)
45. Fairport Convention, "Who Knows Where the Time Goes" (1969)
44. Jackson Browne, "Late for the Sky" (1974)
43. John Cale, "If You Were Still Around" (1982)
42. Ryan Adams, "Come Pick Me Up" (2000)
41. Throwing Muses, "Hate My Way" (1986)
40. Sinead O’Connor, "Thank You for Hearing Me" (1994)
39. The Go-Betweens, "Dusty in Here" (1983)
38. Simon & Garfunkel, "The Sound of Silence" (1965)
37. Sugarland, "Very Last Country Song" (2008)
36. Phil Ochs, "Rehearsals for Retirement" (1969)
35. Lorraine Ellison, "Stay With Me" (1966)
34. The Velvet Underground, "Candy Says" (1969)
33. Fiona Apple, "Never Is a Promise" (1996)
32. 10CC, "I’m Not in Love" (1975)
31. Judy Garland, "Over the Rainbow" (1939)
30. Big Star, "Holocaust" (1978)
29. Frank Sinatra, "One for My Baby (And One More for the Road)" (1958)
28. The Cure, "Pictures of You" (1989)
27. Annie Lennox, "Why" (1992)
26. Aretha Franklin, "Ain't No Way" (1968)
25. Dolly Parton, "Jolene" (1973)
24. The Carpenters, "Superstar" (1971)
23. Elvis Costello/Burt Bachrach, "God Give Me Strength" (1998)
22. John Lennon, "Mother" (1970)
21. U2, "One" (1992)

Top 20:

20. The Band, "Tears of Rage" (1968)
Co-written by Bob Dylan and Band pianist Richard Manuel, this slow-burn ballad gets much of its emotional punch from Manuel's anguished wail. It's one of rock's most haunting vocal performances.

19. George Jones, "He Stopped Loving Her Today" (1980)
How did the hopelessly devoted subject of Jones' poignant country classic finally quit his long-gone but still pined-for love? He died. Seriously: "They placed a wreath upon his door / And soon they'll carry him away / He stopped loving her today."

18. Bill Withers, "Ain’t No Sunshine" (1971)
Withers was working in a factory making airplane toilet seats when he wrote this remarkably bleak but beautiful R&B ode to longing for someone when she's gone.

17. Yeah Yeah Yeahs, "Maps" (2003)
The stunning desperation Karen O displays on this impassioned plea to a lover about to leave proves her pain is real. It's as if she knows there's nothing she can say to keep him at home, but can't help putting up a good fight anyway.

16. Neil Young, "The Needle and the Damage Done" (1972)
Young's heartfelt but unflinching song about Crazy Horse member Darren Whitten's heroin addiction was rendered even more tragic when Whitten died of an overdose at the end of 1972.

15. Beck, "Lost Cause" (2002)
On the saddest track of Beck's saddest album, love hasn't just slipped away -- it's no longer worth fighting for, replaced by apathy and pretty, pretty exhaustion.

14. Bonnie Raitt, "I Can't Make You Love Me" (1991)
Is there anything more heart-wrenching than begging someone to make love to you one last time -- knowing they don't want you anymore? Can't think of it.

13. Roy Orbison, "Crying" (1961)
The flip side of his fame would always remain the jaunty, Julia Roberts-friendly "Pretty Woman," but the orchestral sweep and chest-squeezing sorrow of the rock pioneer's ululating ballad remains an unforgettable musical marker of "I'm not over you" despair.

12. Joy Division, "Love Will Tear Us Apart" (1980)
Song as suicide note? Doesn't get much sadder than that. Released just before frontman Ian Curtis took his own life, the beautifully morbid tune is believed to spell out the joyless division the singer and his wife, Deborah, were experiencing in real life. As an apparent statement of fact, she had "Love Will Tear Us Apart" inscribed on Curtis' headstone.

11. Elliott Smith, "Between the Bars" (1997)
Smith's ode to drinking away his depression poignantly encapsulates the work of an artist whose gifts were both a blessing and a burden.

Top 10:

10. Billie Holiday, "Good Morning, Heartache" (1946)
"I've got those Monday blues / Straight through Sunday blues": Have the weekly blahs ever been conveyed more eloquently than in Lady Day's jazz standard?

9. Prince, "Purple Rain" (1984)
U never meant 2 cause us any sorrow? U never meant 2 cause us any pain? Well, we never wanted 2 be your weekend lover. We only wanted to 2 be some kind of friend. Think on it, Prince. Think on it.

8. The Beatles, "Yesterday" (1965)
There have been scads of songs about the urge to turn back time and right old wrongs, but no tune captures that feeling quite as beautifully as "Yesterday."

7. Fleetwood Mac, "Landslide” (1975)
Written by a young Stevie Nicks, this ethereal, melancholic tune about change and growing older becomes even more poignant with the maturing of its author.

6. Eric Clapton, "Tears In Heaven" (1992)
The guitarist responded to the accidental death of his four-year-old son with this devastating lament that makes horribly clear the chasm that now lies between Clapton and the loved one he has lost.

5. Al Green, "How Can You Mend A Broken Heart?" (1972)
Reverend Green asks a reasonable question in his cover of the Bee Gees' lament. But if heartbreak causes him to raise the query in such a silkily soulful fashion, we're not going to get too upset that he doesn't find the answer.

4. R.E.M., "Everybody Hurts" (1993)
Michael Stipe sounds like a bleating lamb who lost his mother on this overplayed but still devastating song, which keenly summarizes a universal truth atop a swooning string section.

3. Johnny Cash, "Hurt" (2002)
The Nine Inch Nails original conjures a sad-if-sadomasochistic glee. Johnny's tear-inducing cover reinterpreted those mixed feelings into ones of genuine loss and heartache.

2. Otis Redding, "I've Been Loving You Too Long" (1965)
The most soulful song ever? Redding's rasp sounds like he'd been crying for a week before laying down the track, and the blaring horn build-up hits like a punch in the stomach. Almost physically painful to listen to.

1. Hank Williams, "I'm So Lonesome I Could Cry" (1949)
Williams is so down, even the birds seem like they've lost their will to live. Throw in a mournful, clip-cloppy beat and a sobbing fiddle, and you might as well just lie down on the railroad tracks right now. Which is exactly what we feel like doing after compiling this list. We're going to go listen to "Shiny Happy People" a few hundred times now…

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