By Rob Brunner
Updated April 16, 2009 at 12:00 PM EDT

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. 1.

The list begins with the lamentations of one George Michael, and travels through to… well, we won’t spoil it. But be sure to keep reading after the jump to learn the full extent of our pain. And, of course, the comment section is open so you can let us know where we got it right, where we went wrong, and what we left off. But be gentle. We’re sort of in a fragile place right now. (Entries written by Jason Adams, Rob Brunner, Clark Collis, Leah Greenblatt, Sean Howe, Beth Johnson, Jeremy Medina, Whitney Pastorek, Michele Romero, Aly Semigran, and Simon Vozick-Levinson.)

50. Wham!, “Careless Whisper” (1984)

A cheesy yet expressive sax riff and some choice thoughts on the rhythmic deficiencies of guilty feet make George Michael and Andrew Ridgeley’s ode to cheater’s remorse a classic.

49. Sufjan Stevens, “John Wayne Gacy Jr” (2005)

The only song about a real-life serial murderer on our list, Stevens’ intimate, piano-strewn portrait of a killer is truly a masterwork of creeping devastation: “He dressed up like a clown for them / With his face paint white and red / And on his best behavior / In a dark room on the bed he kissed them all.”

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)

A heart-wrecking symphony of slow-waltzing piano, keening violins, and utterly woebegone vocals, Davis’ country crossover hit paints an indelible picture of post-breakup misery: “Why does the sun go on shining? / Why does the sea rush to shore? / Don’t they know it’s the end of the world / ‘Cause you don’t love me any more?”

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)

If you just read the words on a page, this isn’t particularly heartbreaking (“I am not alone while my love is near me” is hardly the stuff of tragedy). But Sandy Denny’s aching voice and a nostalgia-attack chorus make this a sad classic anyway.

44. Jackson Browne, “Late for the Sky” (1974)

“Looking hard into your eyes, there was nobody I’d ever known,” Browne sings on this intimate peek at a crumbling relationship. “Such an empty surprise to feel so alone.” Bedroom navel-gazing at its best.

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)

This song from Adams’ appropriately named album Heartbreaker implores a lover to humiliate him all she wants, if she’ll only come back to him.

41. Throwing Muses, “Hate My Way” (1986)

The lyrics might seem a little too teenage-diary (“So I sit up late in the morning / And ask myself again / How do they kill children? / And why do I want to die?”), but Kristin Hersh backs it up with a coo-and-growl performance that’s totally unhinged.

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)

“Hello darkness, my old friend.” The delicate harmonies of the then-nascent NYC folk duo spoke to a singular kind of loneliness — one that seeps in despite the constant noise and crowd of city life.

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)

The underrated folk singer’s reluctant goodbye to the world must have been painful enough to hear when it first came out and his career was still active. Listening to the same words now with the knowledge that Ochs would take his own life seven years later is almost unbearably tragic.

35. Lorraine Ellison, “Stay With Me” (1966)

As the story goes, Ellison only recorded this with a full orchestra because Frank Sinatra cancelled on a session after they’d assembled. Her voice could have overpowered five symphonies.

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)

A choir of processed vocals — beautiful but weirdly chilly, like Stepford wives — provide the perfect backdrop for this anthem of blocked emotions.

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)

No, the lyrics (“You’re a wasted face / You’re a sad-eyed lie / You’re a holocaust”) are not perky, and the weeping guitar and cello aren’t cheery either. But the real knife-twister is Alex Chilton’s voice, which slips and slides around the proper key and never sounds like a put-on.

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)

Originally recorded by Delaney and Bonnie as “Groupie (Superstar),” it’s written from the point of view of a woman waiting for her musician lover to return to her. Karen Carpenter’s yearning, hopeful performance makes you feel utterly devastated at the thought that said musician is probably now several more sexual conquests down the road.

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)

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 Danny 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.

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…

UPDATE: Click here for the ten heartbreaking songs we wish we’d included on this original list.

Photo credit: Dumbo: Everett Collection