Ever since the first caveman bellowed grunts of recrimination or reconciliation through a conch shell, music has served as both the messenger of bad romantic tidings and a broker of renewed peace. Whether you're in need of an iPod attached to a nosegay of forget-me-nots, or a cheap-ass CD-R duct-taped to a brick hurled through a window, use the lists below to ensure your message of love (or hate) comes through loud and clear.
• "Goodbye to You," Screeching Weasel Not only does this whiny, Ramones-y piece of punk-rock trash hail from an album called You Broke My Fucking Heart (aka the greatest album title ever), therefore making it a doubly perfect breakup song, it's also really repetitive and irritating —kind of like living with a broken heart!
• "Like a Fool," Superchunk Who is really at fault — the one who trusts, or the one who is untrustworthy? This song addresses that issue, sort of, and is about six different kinds of awesome in the first two minutes alone. Oh, and the answer is that betraying someone's trust is a really fucked-up thing to do and basically unforgivable.
• "One of Us Cannot Be Wrong," Leonard Cohen Because every breakup mixtape needs a little crazy. As soon as the heartbreaker who receives this mix hears Cohen's signature mournful croon, they'll probably expect some "Hallelujah"-type balladry to follow. But unless they really know their Cohen deep cuts — and if they don't, there's another reason you're better off on your own — they won't know what hit 'em once the howling starts!
• "All My Little Words," Magnetic Fields Only a really, really horrible person could not be moved by this song. "I could make you rue the day / But I could never make you stay," it goes. Let's focus on the "make you rue the day" part.
• "You're Gonna Miss Me," Ann Sexton Because sometimes you've just got to try to funk away the pain. Hey, these can't all be weepers. What are you, pathetic or something?
• "The Last Day of Our Acquaintance," Sinead O'Connor Q: Can we still be friends? A: No. Also, I anticipate the utter detachment with which you will regard me, still, long after this pain has dulled, and want you to know that on top of being a stupid jerk, you are something even worse: utterly predictable.
• "If I Had a Heart," Fever Ray And you know why I don't have a heart anymore, don't you? (Also, this song is really creepy.)
• "4'33"," John Cage This one might require a little annotation. For instance, "Dear Person Who Broke My Heart: I shall never taste your sweet lips again, but please be sure to listen to this last song all the way through. It totally expresses everything I have to say to you right now."
• "I Want You Back"/"I'll Be There," The Jackson 5ive So which one are you: the idiot who breaks off a great thing and realizes almost instantly he's Super-Glued clown shoes to his feet, or the dumped guy who believes if he just plays it a little cool, love and sweet patience will win out? Either way, the romantic wisdom of 12-year-old Michael Jackson has you covered.
• "When You Were My Baby," Magnetic Fields OK, you might have to explain lines like, "Everybody began to hate you / When you were my baby." But if you want to remind him/her of the good times while appealing to any nostalgia they have for the two of you as a unit, this staggeringly lovely Phil Spector knock-off should do the trick.
• "Where or When," Frank Sinatra Use the gloriously melodramatic version on the CD reissue of Sinatra Sings for Only the Lonely — a record you should be well-acquainted with by now, you loser, you. Sinatra delivers this Rodgers & Hart jewel about a chance encounter between former lovers like an amnesiac getting back a lifetime of beautiful memories in an instant.
• "The Beautiful Ones," Prince In Purple Rain, Prince somehow sings this histrionic space ballad with enough passion to cloak the fact that he's the one being a total dick. Don't try this at home, unless your loved one is as gullible as Apollonia.
• "Nothing Compares 2 U," Sinead O'Connor If you want to tell someone your life has been shipwrecked on Crap Island ever since they handed back the apartment key, there's never been a line more eloquent than, "It's been seven hours and 15 days / since you took your love away." If it doesn't work, say hello to a weepy all-nighter with Ben & Jerry's and the Criterion Chungking Express.
• "I'm in Love With a Girl," Big Star A basic truth of human existence is that everyone, at some point, craves the kind of full-hearted, unguarded, helpless longing Alex Chilton owns up to in this barely two-minute heartbreaker. Sex reversal: Suzanne Vega's disarming "Gypsy."
• "Ooh Child," The Five Stairsteps The Stairsteps' majestic 1970 single extends the promise of better times like a hand up from a fall. If parting has been equally rough on both of you, we predict a tearful reconciliation in 3:18.
• "Down So Low," Tracy Nelson If Miss Tracy's devastating kiss-off to a damnably enticing ex doesn't lead to the hottest makeup sex you've ever had without rocking an elevator off its cables, consult a physician.
• "God Only Knows," The Beach Boys The sound of adoration undying. I may not always love you, Brian Wilson says, splitting hairs in a manner more Byronic than Clintonian — but as long as there's sky over your head, you're safe. Bonus points: If it works, your loved one will get choked up every Christmas when TBS reruns Love Actually.
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