Crybabies

Entertainment Weekly lists the Top 50 heartbreaker songs:

50. Wham!, "Careless Whisper" (1984)
49. Sufjan Stevens, "John Wayne Gacy Jr" (2005)

48. Meshell Ndegeocello, "Bitter" (1999)
Ndegeocello's songs have ranged over all sorts of unexpected genres throughout her career. Her third album's title track, a stripped-down lament for a failed relationship, may pack more emotional punch than any of them.
47. Skeeter Davis, "The End of the World" (1962)
46. Lauryn Hill, "Ex-Factor" (1998)
Forget screaming fights. Nothing sums up the final impact of a break-up like Hill's melodic sigh of resignation in this tune.
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)
Cale sounds like he's singing while curled up in the fetal position on the bathroom floor. And Sam Shepherd's lyrics are positively chilling: "If you were still around / I'd tear into your fear / leaving it hanging off you in long streamers / shreds of dread."
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)
It's not the obvious gut-wrencher from the Irish pixie, but it sure is the right one. Where "Nothing Compares 2 U" comes at you straight up the middle, "Thank You for Hearing Me" (off of 1994's Universal Mother) lulls you into a false sense of security with reassuring verses like "Thank you for loving me," only to wallop you over the head with this doozy: "Thank you for breaking my heart / Thank you for tearing me apart / Now I've a strong, strong heart / Thank you for breaking my heart." Yeah.
39. The Go-Betweens, "Dusty in Here" (1983)
Grant McLennan's father died when he was four. Twenty years later, he wrote this bleak tribute, and its echoing empty spaces beautifully capture muted anguish for a loved one long-gone. When McLennan himself died three years ago, it took on even greater resonance.
38. Simon & Garfunkel, "The Sound of Silence" (1965)
37. Sugarland, "Very Last Country Song" (2008)
It's nice to think about a world without loss, pain, or regret, a world in which we wouldn't require forlorn ballads like this one. And then you realize that world will never exist, and we're all gonna die alone, and it's not so nice anymore.
36. Phil Ochs, "Rehearsals for Retirement" (1969)
35. Lorraine Ellison, "Stay With Me" (1966)
34. The Velvet Underground, "Candy Says" (1969)
"I've come to hate my body / And all that it requires," late-period bassist Doug Yule sings over hushed guitar chords in this song, reportedly written in honor of transgender Andy Warhol associate Candy Darling. It's one of Lou Reed's simplest compositions, and one of his most powerful.
33. Fiona Apple, "Never Is a Promise" (1996)
The crown princess of '90s piano angst dug deep on this fierce, fragil ode to supreme isolation, singing desperately of a fever that "burns me deeper than I’ve ever shown."
32. 10CC, "I’m Not in Love" (1975)
31. Judy Garland, "Over the Rainbow" (1939)
The poignant plea at the heart of The Wizard of Oz speaks to our fantasies of flying away to a pain-free (and, sadly, impossible) paradise "where troubles melt like lemondrops."
30. Big Star, "Holocaust" (1978)
29. Frank Sinatra, "One for My Baby (And One More for the Road)" (1958)
In the aftermath of his painful divorce from Ava Gardner, Sinatra recorded Only the Lonely, one of the ultimate heartbreak albums. On this oft-covered track, he implores a bartender to help him drink away the pain and memories.
28. The Cure, "Pictures of You" (1989)
No amount of twinkly chime-shimmering can mask this song's tragic truth: When you've been staring at pictures of your ex for so long you actually start to have tangible hallucinations about said ex, that's bad.
27. Annie Lennox, "Why" (1992)
When Annie Lennox desperately cries to her lover, "Why can't you see this boat is sinking?" it's instantly familiar to anyone who has fought to the end in a deteriorating relationship. Her haunting voice makes this plea for forgiveness all the more despairing.
26. Aretha Franklin, "Ain't No Way" (1968)
Technically a b-side to another single, this cri de coeur turned out to be one of the Queen of Soul's crowning jewels.
25. Dolly Parton, "Jolene" (1973)
It's a simple request: You can have any man you want, Jolene; please don’t take mine. That brittle tremble in Parton's voice is desperation defined.
24. The Carpenters, "Superstar" (1971)
23. Elvis Costello/Burt Bachrach, "God Give Me Strength" (1998)
Originally written for the film Grace of My Heart, this desperate prayer to survive love lost hits a crescendo when it speaks to the naked truth of being dumped -- "See, I'm only human, I want him to hurt."
22. John Lennon, "Mother" (1970) Over sparse piano chords, drums, and bass, Lennon laments his long-departed mum (and the father who abandoned them), and then shows what he's learned in primal-scream therapy.
21. U2, "One" (1992)
The third single from the Irish superstars' 1991 album Achtung Baby remains one of the band's most beloved touchstones (and, somewhat counter-intuitively, a wedding favorite).
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)
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)
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.
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