Johnny Cash, "Hurt"
Entertainment Weekly created a list of the 50 most heart-breaking songs of all time. It's a pretty good list, and below are some highlights (all commentary written by the EW staff). I was going to include some of the suggestions from the commenters, but so many of them picked Adult Top 40 songs (The Fray's "How to Save a Life," really?) that I think a lot of them missed the point of the list.
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."
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.
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.
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.
[Side note: It's hard for me to hear this song without immediately thinking of Notting Hill.]
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.
[Side note: Remember when Carrie Underwood auditioned with this piece?]
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.
[Side note: How is this song not #1? In my very limited opinion, this is the best song ever written.]
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.
And then, EW realized they had some glaring omissions and wrote another list of ten, including Jeff Buckley's "Hallelujah," Joni Mitchell's "River," Radiohead's "Fake Plastic Trees," and Tom Waits' "Ruby's Heart."