We made a list of heartbreaking songs. You read it, and let us know what we left out. Many, many things we left out. After reading all of your excellent suggestions, we realized that we’d forgotten some pretty key stuff. So consider these ten additions (one just below, plus nine more after the jump) to be part of our original list — a new, improved list of the 60 most heartbreaking songs of all time. Thanks for all of your ideas! If we’d done a list of 1,000, all of them would have been on there. (Entries written by Rob Brunner, Clark Collis, Leah Greenblatt, Whitney Pastorek, and Simon Vozick-Levinson.)
Jeff Buckley, “Hallelujah” (1994)
Even without Buckley’s tragically premature death, the plaintive wail of his tenor covering Leonard Cohen’s breakup hymn would still move us to tears every goddamn time. So heartbreaking, even overkill on The O.C. couldn’t diminish its power.
Patsy Cline, “I Fall To Pieces” (1961)
The Queen of Country’ssimple version of the Hank Cochran and HarlanHoward-penned tune perfectly encapsulates the weak-kneed,room-swimming-before-the-eyes, going-to-hurl-lunch feeling you get whenseeing a former lover who still owns your heart. Though let’s be clearthat lunch-hurling is not explicitly mentioned.
Joni Mitchell, “River” (1971)
In Mitchell’s ruminative classic it’s Christmastime, and what’s under the tree? Tears. Her lonesome desire for “a river to skate away on” has since been echoed by artists from k.d. lang to Corinne Bailey Rae, but nothing unfurls holiday heartbreak quite like Joni’s original.
Harry Nilsson, “Without You” (1971)
“Without You” was written and originallyrecorded by Welsh rockers Badfinger. But it was the troubled,velvet-voiced Nilsson who topped the charts with a version that framedthe story of faux resignation and utter desperation in abeautiful Beatles-esque arrangement. In 1994 Mariah Carey also scoredbig with a far more vocally gymnastic version of the track that wasreleased shortly after Nilsson’s alcohol-hastened early demise.
Radiohead, “Fake Plastic Trees” (1995)
How many bands have gottenrich by carbon-copying the blueprint set down on this exquisite bit offalsetto mopecore? At least a dozen, surely, but not one has outdonethe original model’s perfectly pitched gloom.
The Smiths, “Please Please Please Let Me Get What I Want” (1984)
Sung by a man whose entire musical oeuvre seemed built on thwarted desires and self-denial, Morrissey’s mournful acoustic plea — “Lord knows it would be the first time” — seems doomed to inevitable, crushing failure.
Bruce Springsteen, “The River” (1980)
Boy meets girl. Boy gets girlpregnant. Boy and girl settle into a lifetime of blue-collardisappointments, dreaming of a redemption that they know will probablynever come. “The River” boils all the big Springsteen themes down totheir rawest essence, delivering an emotional wallop that’s unmatchedin the Boss’s catalog.
The Verve, “The Drugs Don’t Work” (1997)
Verve frontman Richard Ashcroft’sstring-soaked ballad apparently shares a subject with the Go-Betweens’ “Dusty in Here” (No. 39 on our original list)– and it’s similarly devastating. The beautifully crafted,passionately sung track reportedly deals with Ashcroft’s father dyingfrom cancer.
Tom Waits, “Ruby’s Arms” (1980)
Nobody does weepy piano ballads like Waits, and this tale of hipster-hobo love lost is one of his saddest. By the time he drags himself to the climactic wail “I’ll never kiss your lips again,” he sounds like he’s been up for a week, chain-smoking Chesterfields and downing bottle after bottle of bourbon. He probably had been.
Warren Zevon, “Keep Me In Your Heart” (2003)
Half a decade after his death, it is still difficult to hear any song by Zevon without feeling a little sad (okay, maybe not “Werewolves of London”). But “Keep Me In Your Heart” is the musical equivalent of a three-hanky movie — a poignant, desperate plea to be remembered, at least “for a while,” sung by someone who was all too aware that he soon really would be just a memory.
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