The 50 Worst Songs Ever! Watch, Listen and Cringe!

10. PAUL McCARTNEY AND STEVIE WONDER “Ebony and Ivory” 1982
Racial-harmony dreck



See, it’s a metaphor: “Side by side on my piano/Keyboard/Oh, Lord/Why don’t we?” McCartney and Wonder want the races to get along as peacefully as the white and black keys on a piano — which seems unlikely, since the white keys didn’t enslave the black keys for hundreds of years. The anguished idealism inspired a Saturday Night Live duet between Eddie Murphy and Joe Piscopo: “I am dark and you are light/You are blind as a bat and I have sight.”
Worst Moment The repeated chorus at the end — where the song gets even chirpier.


9. MADONNA “American Life” 2003
Desperately seeking…contemporary relevance



On which Madonna updates the “Material Girl”–era satire of commercialism and spiritual emptiness — but this time, she does it with what is hands-down the most embarrassing rap ever recorded. Nervous and choppy, she makes Debbie Harry sound as smooth as Jay-Z. The only thing worse than shouting “soy latte”? Rhyming it with “double shot-ay.” The rhymes don’t kick in for a full three minutes, but the song — propelled by a constipated digital beat and some bungled musings on celebrity culture — stinks the whole way through.
Worst Moment After rapping, Madonna sings, “Nothing is what it seeeems” in a manner drained of all profundity.


8. EDDIE MURPHY “Party All the Time” 1985
Beverly Hills Cop commits felony pop



Now, it might seem like a cruel satire: Leather-suited comedian teams up with Jheri-curled Superfreak to craft hit record. But no — in 1985, Eddie Murphy and Rick James really did get to number 2 with this catatonic checklist of funk clichés: the witlessly parping synthesizers, electro-totalitarian drums that are practically ready to invade Poland on their own, production mimicking karaoke night in an abandoned pet-food factory and…falsetto singing!
Worst Moment James oozes, “She-likes-to-paaarty — all — the — tiiiime,” leaving us in no doubt about what kind of “party” he has in mind. Relax, ladies: He was on crack.


7. BOBBY McFERRIN “Don’t Worry Be Happy” 1988
Oh, great — a bumper sticker set to music



Just as there are few things more depressing than being told to cheer up, it’s difficult to think of a song more likely to plunge you into suicidal despondency than this. The finger-clicking rhythm, the Sesame Street backing and McFerrin’s various accents — all different, all patronizing — are an object lesson in trying too hard. The lyrics are appalling, too: If your landlord is indeed threatening you with legal action, you should not under any circumstances follow McFerrin’s advice, which seems to involve chuckling at him and saying “Look at me, I’m ’appy” in a comical Jamaican voice.
Worst Moment The whole wretched thing.


6. HUEY LEWIS AND THE NEWS “The Heart Of Rock & Roll” 1984
A celebration of rock music… by a band seemingly intent on destroying it



Less a song than a craven attempt to curry favor from drunken arena crowds trained to roar on cue when they hear their city’s name mentioned. Coming off more like one of your dad’s golf buddies than a rock star, Lewis rattles off a list of American cities in a monotone so bland that subbing in “Bakersfield” for “San Antone” would drive the fans wild, and hopefully distract them from the fact that the bar band–caliber music suuuuucked.
Worst Moment The second verse, when that cheeky Huey almost uses the word ass. Ah, 1984 — such a simple time.