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9. The Smiths, "I Know It's Over" (1986)
"I Know It's Over" finds the normally self-obsessed Morrissey stunned into a place of universal compassion. A breakup has rendered him vulnerable to the point of fetal ("The sea wants to take me/ The knife wants to slit me"), but he finds a way to a profound insight: "It's so easy to laugh, it's so easy to hate/ It takes strength to be gentle and kind." Over nearly six minutes, he touches on nearly every aspect of breakup psychology. The song is vast, chilling, and completely devoid of The Smiths' usual winking. — P.S.
8. Bill Withers, "Ain't No Sunshine (When She's Gone)" (1971)
"Ain't No Sunshine" is in an unusual key — "pure minor," which is rare in pop music. Maybe it's that, or Withers' devotional repetition of "I know" in the third verse, but the song comes across less as vintage '70s R&B and more as something older; something sacred, even. — A.H.
7. Etta James, "I'd Rather Go Blind"
Over a hypnotic, two-chord vamp, Etta James bares her soul to the point of bloodletting. Her performance starts off relatively low-key and mournful, but by 1:30 ("I was just, I was just, I was just sitting here thinking of your kiss, and your warm embrace"), she's fully in the over-the-top truth of the song: sometimes, it'd be easier to never see again than see someone you love walk away. — A.H.
6. Smokey Robinson & The Miracles, "The Tracks of My Tears"
Smokey Robinson's gossamer vocals are downright angelic on this song: his voice is so pure, and his pain so impossibly transparent, it's like looking through a beautiful window into a house destroyed by fire. The song's dynamic shifts have a lot to do with its success as well: as the restrained verse accelerates into that skyrocketing chorus, the strings swell, the drums crash, and Smokey's voice wavers above it all, sounding, well, like an angel. — A.H.
5. Harry Nilsson, "Without You" (1971)
When he first heard Harry Nilsson sing, Little Richard was supposed to have said, "My! You sing good for a white boy!" That is a dramatic understatement. "Without You" is such a commanding performance carried off with such tenderness that when Nilsson's voice cracks on that heroically high note at 2:09, you're a little unsure as to whether it was too tough on him physically or emotionally. Either way, wow. — A.H.
4. Prince, "When You Were Mine" (1980)
The perfect craft of "When You Were Mine" might conceal the hurt at its core. No one would blame you for getting distracted by the huge guitar, vocal, and keyboard hooks — or by the revolutionary-for-its-time gender ambiguity of the narrative. But under all that is a simple, biting observation about human nature: "I love you more than I did when you were mine." — P.S.
3. Outkast, "Ms. Jackson"
This is probably the only breakup song ever addressed to the singer's mother-in-law, but the gambit pays off. By directing his imploring lines to Erykah Badu's mom instead of Badu herself, Andre 3000 makes an implicit statement about how the idealism of young love ("that crib with the Goodyear swing") gives way to the complexities of adulthood: private schools, day care, lawyers. Mothers-in-law. It's rueful, but it's loving too. — P.S.
2. The Beatles, "For No One"
Among Paul McCartney breakup songs, conventional wisdom would give the edge to "Yesterday." But while "Yesterday" is certainly beautiful, with its sweeping strings and simple lyrics, it's more adolescent in its mood than the brutally adult "For No One." Here, McCartney strips out all sentiment in favor of a crisp, hard-headed look at the end of a relationship. It's devastating (and very English). "Yesterday" feels speculative, and McCartney wrote it when he and Jane Asher were still happily together; "For No One," written while they were breaking up, could only have been written by someone who'd been there. — P.S.
1. Bob Dylan, "Don't Think Twice, It's All Right"
Dylan wrote this classic after his girlfriend, Suze Rotolo (who appears on the cover of The Freewheelin' Bob Dylan), told him she was extending her trip to Italy... indefinitely. In a perfect expression of rejection and bitterness, Dylan fills this song with slow burns like "I once loved a woman, a child I'm told/ I give her my heart but she wanted my soul," and of course, that final punch to the stomach, "You could have done better but I don't mind/ You just kinda wasted my precious time/ But don't think twice, it's all right." There's really no better song to listen to when you're hurt but don't want to hurt your pride. — R.K.
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