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39. New Order, "Age of Consent" (1983)
In an angsty moment, count on a great keyboard riff to make you feel like it's going to be okay. See "Age of Consent." At once calming, classy, and catchy, this is a requiem for a mostly-adult relationship. Maybe the Brits are just more composed than us, but, while cutting, "Age of Consent" also sounds almost polite. — Rachel Krantz
38. No Doubt, "Don't Speak" (1996)
Originally a celebration of love between Gwen Stefani and Tony Kanal, "Don't Speak" was later rewritten to reflect their breakup. Through Stefani's remorse-laden voice, it reminds of us the times we want to shrink away from the harsh truth, and choose silence over angry words. — J.G.
37. Jeff Buckley, "Lover, You Should've Come Over" (1994)
Jeff Buckley's more known for his epochal cover of "Hallelujah," but "Lover, You Should've Come Over" showcases the sophistication of his own songwriting. With chords more inspired by jazz than rock and a voice that sounds decades wearier than it has any right to, "Lover" is an elegiac ode to lost love from someone who seemed to know more about losing love than any of us. — A.H.
36. Notorious B.I.G., "Friend of Mine" (1994)
This is an ode to those relationships in which both parties screw everything up royally. Biggie gives us the backstory of himself and his lady, which is rife with lies, infidelity, and smack-talkin'. Sometimes the only direction you can point your finger is at yourself. — J.G.
35. Liz Phair, "Fuck and Run" (1993)
The musical, lyrical, and spiritual opposite of "November Rain," "Fuck and Run" is wistful and blunt. A not-very-passionate relationship is dropping off, and it sounds like it's only the most recent of many. This is the lament of someone who wants something more, but is too paralyzed to reach for it. — P.S.
34. Bon Iver, "Skinny Love"
If you're trying to make haunting breakup music, heading into exile in the woods of Wisconsin is almost cheating. But the results speak for themselves. This is heartache on a different level; sadness for the one who left and remorse for the person you've become. — J.G.
33. The Walkmen, "The Rat" (2004)
To really understand this song, you need to watch a live version and see how furiously guitarist Paul Maroon strums the intro. Then Matt Barrick starts beating his drums like they killed his dad, and one of the most righteously pissed-off breakup songs of the decade is off to the races. It's a gloriously spiteful kiss-off, and one perfect for pounding the pavement after a breakup. — A.H.
32. Roy Orbison, "In Dreams"
Roy Orbison's best songs are operatic, in the best sense of that word. Not just because of his preternaturally athletic voice, but because of their narrative momentum. "In Dreams" is a perfect example: in contrast to the rigid structure of most pop music, the song moves forward, unfolding new sections rather than returning to old ones. When Orbison hits that spine-tingling high note at 2:28, it's like every third-reel climax rolled into one beautiful moment. — A.H.
31. Led Zeppelin, "Tangerine" (1970)
"Tangerine" should probably appear in the dictionary next to the word "wistful." With its sweet vocal harmonies and beautiful slide guitar, it's a perfect picture of a past relationship that hasn't quite lost its ache in the recollection. — P.S.
30. The Jesus and Mary Chain, "Just Like Honey" (1985)
With brutal honesty, "Just Like Honey" describes what runs through your brain when you find yourself back with the person who can only be described as a total life ruiner: "I'll be your plastic toy." It'll give you that desperate moment of clarity you need if you find yourself making all the wrong choices. — J.G.