Staff Top 10
Top 10 Breakup Songs That Instill An Ironic Sense of Hope

like ivy, spreading itself across every manner of genre and psyche, the love song veils itself as freaky synecdoche (Newsom), sad, solitary bedroom dance parties (Maricich), or old-fashioned death marches (Nilsson.) But there exists a sub-phenomenon known as the I’m Really Happy We Broke Up Breakup Song, not to be confused with the I’m Pretending I’m Happy But Really I’m Furious And Jealous Breakup Song (Clarkson) or the I’m Really Glad We Were Together Because I Learned A Lot From You Breakup Song (Houston).

This is different. It’s a subcategory in which the nefarious, the ambiguous, the nonchalant, and—most importantly—the major key coincide, collaborate, and make of a sad fact of life some of the most pleasurable creations in popular musical history. You’ll recognize every single song here, but it’s a tiny nuance of, “No way does love lasts forever and it’s kind of more entertaining that it doesn’t” that we’re after.

That said, the taxonomy of breakup is very complex, and there are numerous subcategories beneath the weird one I’ve chosen. Kinda like Grief, but much more arrayed.

01. I Wish We Were Broken Up
Dr. Dre – Housewife
2001, as with most Dre material, was laden with money-grub baby-mama misogyny, but it was “Housewife” that exalted this filthy genre to the category of “breakup,” in spite of the fact that the “housewife” in question stands as more of a symbol of a figment of a pain in the ass in the general gestalt of the rich rapper. “Housewife”’s seasoned coke habit, fake pregnancies, and other “broad turned fraud” antics leads Dre to preach to the choir about how “the homies not doing it right…you can’t make a hoe a housewife,” though by god, many will try, he knows. It’s the self-awareness, the willingness to learn from one’s mistakes, the bitterness, and the relatable nature of the phenomenon, as endorsed by pithy contributions from Hittman, Kurupt, and D.O.C., that makes “Housewife” an ironically hopeful breakup song through and through.

Rival Taxonomy: I Digs You, But I’m Not Going To Act Like It Around My Friends…Or On The Radio.

02. I’m Too Young For This
Billy Bragg – A New England
It’s hard to tell whether the loner of punk actually did the breaking up here, or whether it has even been done yet. The 22-year-old specimen harps not only on his girlfriend’s apparent disinterest, but the impending doom he feels for having to tell her he doesn’t want to hang out with her anymore. Youthfulness and sagacity have rarely been as well aligned on a breakup song as when Bragg says, “I don’t feel bad for letting you go, I just feel sad about letting you know.” It’s the happy guitar and lyrical simplicity that seal the deal, compounding meaning in a cliché as old as time.

See Also: You Actually Mean A Lot To Me, But I Can’t Take All Your Drama.

03. The Label Wanted Us To Write A Hit
Radiohead – High and Dry
Thom Yorke has often expressed his willingness to erase “High and Dry” from his band’s grand oeuvre, but there’s no sense in speculating that the song lacks lyrical integrity in spite of its proto-Coldplay qualities. Perhaps, still, it’s a momentary breakup of the band with its vision. “H&D;” is not actually about a woman, or a breakup, but it rivals “Thinking About You” as a yearning exposé of a person over which the singer has little control, and fears losing. Judgments creep in (“You'd kill yourself for recognition / Kill yourself to never ever stop / You broke another mirror / You're turning into something you are not,” but that simple, aching chorus is, enfin, Yorke declaring how much he misses “the real you” of the song’s subject.

See Also: I Feel Like I’ve Already Lost You.

04. Nightclub as Closure
Cher – Believe
When the plastic surgery victim / potential model for weird-looking Sims characters Cher came out with one of the longest-standing number one hits in the history of British music, it was hard not to wiggle to it just a little. Identity crisis #36 saw a handful-of-hits wonder reinventing herself as a one-hit dance floor wonder, complete with a video that took place in a club, in which Cher herself was in some sort of glass cage, watching young people stare at each other through strobe lights. The message, “Do you believe in life after love?” was admittedly poignant (and prescient), especially when paired with the melody’s successful bastardizing of a genre that had already learned to dilute itself enough to be swallowed by FM.

See Also: My Overplayed Anthemic Teen Remedy Gave Me Life After Career Death.

05. See You After Rehab, When Our Relationship Will Be Dramatically Different, Possibly Boring
Verve – Drugs Don't Work
No one knows entirely what this song is about, but the collective public understanding of the Verve’s gut-wrenching masterpiece for all intents and purposes involves a relationship marred by substance abuse that results in, if not separation physically, at the very least a marked distancing from the signs and symbols of the couple’s early whirlwind days, such as “my old street” and “your ear,” which Ashcroft promises he will “sing in” “again” if the lady in question so desires. Their separation is at the heart of the song, and a willingness to admit it’s all for the best is communicated through major-to-minor shifts and a darn triumphant (fine, bittersweet) chorus. “But I know I’ll see your face again” is laden with the sense that while things will never be the same again, at least they’ll be again.

Other Possible Reading: The Antidepressants Don’t Work.

06. You’re A Wild Bird And I Can’t Tame You
Doves – There Goes the Fear
Pre-“O.C.,” the voices on campuses everywhere heralded the British group Doves as one of the big indie bands of the future, possibly sealing their fate as a mostly neglected, kinda slumping indie band of the present. “There Goes the Fear,” a six-plus-minute farewell ode, used cheerful, sped-up, manipulated guitar loops and a romantic hook, “Close your brown eyes / And lay down next to me / Close your eyes, lay down / 'Cos there goes the fear / Let it go,” in which Jimi Goodwin became the most trustworthy fantasy boyfriend in indie rock. It is unclear whether the “fear” in question is actually “coming” or “going,” but the girl in question is most definitely going, which Jimi is OK with in the end: “Think of me when you close your eyes / But don't look back when you break all ties.” Strong man.

See Also: My Sensitivity Will Bring You Back, Dammit.

07. I’m A Rolling Stone; You Don’t Care About Me Anyway
Bob Dylan – Don’t Think Twice, It’s All Right
The king of caring wrote one of his sweetest guitar ditties about a woman who suffered from, well, not liking him very much. The complex, winding guitar riff looped ad infinitum serves as the backdrop to Dylan’s rant, which can essentially be summarized by the words, “It’s too late,” but an awful lot more poetical: not only is there a fundamental rift between the two people, but, he fatefully supposes, there always will be: “And it ain't no use in turnin' on your light, babe / That light I never knowed / An' it ain't no use in turnin' on your light, babe / I'm on the dark side of the road.” The roaming transience of this young man is emphasized for probably the thousandth time in his musical career, serving up one more episode in the singer’s ambulation through geographies and romances.

Take Note: The Antidote To Heartbreak Is, Natch, Skipping Town.

08. I Couldn’t Be Myself Around You
Tori Amos – Tear in Your Hand
Young Tori, on her breakthrough second album, wrote “everyone’s favorite” in reference to what I can only assume was a foolish young man who enjoyed scoffing at her youthful, breezily destructive tastes. With the line, “I can’t believe you’re leaving because me and Charles Manson like the same ice-cream,” we can only speculate that irrelevant and weird (metaphorical) quibbles destroyed this nebulous relationship, causing Tori to speculate that it was not the ice-cream, but “that girl” that ended the romance, and that “there’s pieces of me you’ve never seen, I think [that girl]’s just pieces of me you’ve never seen.” There’s a gleefulness behind this song’s sad state of affairs—a lovely major key that instills optimism in spite of the line “You don’t know how much power you have with that tear in your hand.”

See Also: I Let Down My Guard And I’m Ashamed of It.

09. You’re Gonna End Up With the Backup Dancer
Justin Timberlake – Cry Me a River
The fruits of early Timberlake/land labor produced this infamous Spears reference, complete with a video featuring a Britney look-alike in a now unfashionable newsboy hat. Timbaland’s trademark organic sound effects, synths, and slaps catapulted Timberlake’s music in spite of the feather-hearted libretto of this song: “You don’t know all the ways that I loved you.” The song does not succeed as a closure only because Timberlake still, four years later, writes songs about Britney Spears that say pretty much exactly the same thing. But at the time, this addictive pop sianara was a revolutionary, self-referential, premonitory piece of candy with a flavor lasted months (nay, years).

Works Well With: You’ll Get What’s Coming To You, And He’ll Leave Too, AKA “What Goes Around…Comes Around.” Now Playing.

10. It’s Not Over Yet
D'Angelo - One Mo' Gin
The irony is in the fact that they’ll probably hook up again; the hope is in Angelo’s assumption that they will hook up again, and the breakup factor is downright negligible, because this is one of the sexiest sex songs ever written. The king of groin overexposure here laments about “the precious times we had” to the happy harmonies of a bump-and-grind bass and bubbling keyboard, disclaims “I know you got someone, I got somebody too,” but emphasizes that “you could call me girl when things change.” He suggests that in the meantime he will, in light of the sensual music herein—forget the lyrics—probably fantasize about this peerless ex while in bed with his “somebody too.” Classique.

See Also: This Girl’s Got Nothing On You, Girl.

By: Liz Colville
Published on: 2007-02-02
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