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19. Sam Cooke "Bring It On Home To Me"
Lou Rawls' uncredited backing vocals on this song lend it a commiserating, drinking-buddies-on-a-breakup-bender feel. Cooke and Rawls' voices dip, swell, and surge together, and for all the sadness here, there's a comforting blanket of friendship over the whole song. It's one man with his arm around his friend at the back of the bar, letting him know that he's better off, even if they both know he doesn't really mean it. — A.H.
18. Joni Mitchell, "A Case Of You" (1971)
You really can't talk about breakup songs without talking about Joni. There are lots of strong contenders on Blue, but "A Case Of You" is the one track we don't want to get over. This song could be about a lot of situations — an already broken relationship, a relationship in the process of breaking, or the anticipation of doomed love. So "A Case Of You" will be what you need it to be. — R.K.
17. Elliott Smith, "Oh Well, Okay" (1998)
In a discography full of gorgeous, devastating breakup songs, it's hard to pick just one. (Also nominated: "Say Yes," "Waltz #2," "Miss Misery," "Between the Bars," "The Biggest Lie," "Condor Ave.," etc.) But "Oh Well, Okay" might be the best of the bunch, a sigh of resignation wedded to one of the most beautiful melodies poor Elliott Smith ever wrote. — P.S.
16. Marvin Gaye, "I Heard It Through the Grapevine" (1968)
It was Motown producer Norman Whitfield's idea to have Marvin Gaye sing this song in a register close to the top of his range, so the desperation in his voice is equal parts physical and emotional. But the rest of the song's genius is in the arrangement: sinister electric piano, and pounding tribal drums, a perfect sonic approximation of infidelity-related paranoia. — A.H.
15. Joy Division, "Love Will Tear Us Apart" (1980)
This must be the most sepulchral song ever to have become a massively influential international hit. Maybe it's only in retrospect, but it's almost impossible to hear "Love Will Tear Us Apart" without thinking that someone's about to kill himself. — P.S.
14. Willie Nelson, "Always On My Mind" (1982)
The apology song is a difficult one to pull off — if the song is too self-flagellating, it becomes more about the singer than the person they've wronged. But Willie Nelson gives "Always On My Mind" a perfect balance of regret and resolve. His sandpapery rasp and restrained delivery are the real reason this song — covered by so many others — belongs to him. — A.H.
13. Rod Stewart, "Maggie May" (1971)
The deceptively nuanced lyrics, Stewart's wistful vocal, and the band's rustic, ramshackle feel make "Maggie May" one of the most heartfelt portraits of a disintegrating relationship ever recorded. That it's a May-December relationship doesn't make any difference — this relationship wasn't a novelty to the people in it, and it shouldn't be to the listener, either.— A.H.
12. Fleetwood Mac, "Landslide" (1975)
Unlike most breakup songs, "Landslide" speaks from the moment right before things actually fall apart. Stevie Nicks wrote it while stranded on a mountain in Colorado, contemplating the coming end of her relationship with Lindsay Buckingham; it's melancholic and uncertain, but like many of Nicks' songs, it also has an appealing toughness. Time makes you bolder, after all. I thought this song was sad and pretty when I was half the age I am now; today, I see more in it than that. — P.S.
11. Sinead O'Connor, "Nothing Compares 2 U" (1990)
In my opinion, this is one of the few covers that blows the original out of the water. (My apologies to all the Prince fans out there.) With devastating honesty, Sinead O'Connor mourns a straying lover, while celebrating the freedom of being alone again. Life's great buffet is hers for the taking, but it's all lost its taste. — J.G.
10. Jackson 5, "I Want You Back"
Written about a relationship that ended prematurely, and a lover hastily backpedaling to save it, "I Want You Back" evokes all the mistakes of young lovers in the heat of passion. Regardless of the upbeat tone (and the fact that it was sung by an unusually soulful eleven-year old), this song is a glum reminder that once a relationship is over, something will be lost forever and ever. — J.G.