25
PUFF DADDY FEAT. FAITH EVANS AND 112
“I’ll Be Missing You” 1997
…and your platinum-selling albums. Sob!

A little over three months after the tragic shooting of his best friend, the Notorious B.I.G., a distraught Puffy Combs channeled his grief into “I’ll Be Missing You,” a nauseating brew of gloopy sentimentality and strategic-marketing mawkishness. Opportunistic? Perhaps. But how very therapeutic it must have been for Puffy to have this memorial to his departed chum spend 11 weeks at number 1.

Worst Moment The mumbling insincerity of the spoken-word intro: “I saw your son today.…He looked just like you.”


24
FIVE FOR FIGHTING
“Superman” 2000
Musical kryptonite

In the chaotic days following 9/11, people were grasping at whatever they could find for comfort. But perhaps nothing shows how out of sorts America was than the ascendance of this turgid ballad by once-and-future-unknown John Ondrasik as this grieving nation’s unofficial anthem. Maybe it was the sensitive-guy lyrics (“Even heroes have the right to bleed”) delivered over Billy Joel–lite piano noodling that soothed America’s frazzled nerves. But if this man is allowed to continue recording, then surely the terrorists have won.

Worst Moment Those falsetto notes in the chorus are enough to bring Osama bin Laden and Lex Luthor to their knees.


23
COREY HART
“Sunglasses At Night” 1984
If you look up one-hit wonder in the dictionary, this is what you’ll find

Over a keyboard riff that sounds more than a little like that of “Sweet Dreams (Are Made of This),” the brooding Quebecois Hart mugged worse than Derek Zoolander as he extolled the virtues of going incognito. With its lack of anything resembling a human being playing an instrument, this is disposable synth-pop at its most bubblegum.

Worst Moment The chorus, in which Hart warns, “Don’t switch a blade on the guy in shades, oh, no,” was an attempt at tough-guy posing, but it made him sound like the musical equivalent of Judd Nelson in The Breakfast Club. That is, not very tough at all.

22
TOBY KEITH
“Courtesy of the Red, White and Blue (The Angry American)” 2002
Oklahoma redneck runs for office on Hate ticket

Outraged by the 9/11 terrorist attacks, Toby Keith enlisted in the Air Force — no, sorry, he wrote a fight anthem so vengeful, it makes “The Star-Spangled Banner” sound like “Give Peace a Chance.” Though right-wing radio hosts and politicians called him a hero, Keith (who hadn’t had a hit in years) moaned, “It sucks ass that I have to defend myself for being patriotic.” Wrong. You have to defend yourself for celebrating violence and bloodlust.

Worst Moment“We’ll put a boot in your ass; it’s the American way,” Keith sings, mistaking revenge for ideals of liberty.

21
SPIN DOCTORS
“Two Princes” 1992
This is what happens when jam bands go pop

It’s obviously unfair to dislike a song because of the appearance of the band that recorded it. Yet the very sound of “Two Princes” evokes the way the Spin Doctors looked. With its riff repeated long past endurance, dopey lyrics and abominable vocal scatting, it could only have been the work of scrabbly beared, questionably hatted, red-eyed stoners staggering out of the rehearsal room convinced they have discovered the missing link between grunge, the Grateful Dead and Jamiroquai — blissfully unaware that no one in his right mind was looking for that in the first place.

Worst Moment “Dit-dit-dit! Dit-dit-dit-a-dobba-dobba-dobba dobba!”

20
LIONEL RICHIE
“Dancing On The Ceiling” 1986
The world’s least convincing party song

Sounding suspiciously as if it was written in order to fit a video treatment rather than the other way around, this dispiritingly unfunky celebration appears literally to be about dancing on a ceiling — “People starting to climb the walls.…The only thing we want to do tonight is go round and round and turn upside down.” Even more troubling is the thought that in the ’80s, this rancidly thin stew of AOR dynamics and curiously Rick Wakeman–ish keyboards was Motown’s idea of a hot party record.

Worst Moment The fake party ambience, clearly the work of bored studio employees forced to whoop and cheer.

19
MR. MISTER
“Broken Wings” 1985
The thoroughly nasty sound of yuppie angst

“Broken Wings” is primarily annoying not for its anodyne mid-’80s production, nor for its lyrics, which make its central protagonist sound like someone you would seek a restraining order against (“You’re half of the flesh, and blood makes me whole,” he sings, reaching for the duct tape and the nail gun). It’s primarily annoying because it’s a four-minute intro with no song attached. When the booming drums finally kick in, they announce the arrival not of a fantastic chorus or an epic finale, but the greatest anticlimax in pop, featuring what can only be described as a synth bass solo.

Worst Moment The synth bass solo.

18
CHICAGO
“You’re the Inspiration” 1984
And you thought the Cubs were the biggest losers in this town? Wrong!

It’s hard to believe, but at one point Chicago were a fairly well-respected rock band. Then Peter Cetera joined, and they jettisoned any remaining street cred in favor of soft-rock ballads your grandmother would deem harmless. In this, their most egregious offense, Cetera’s gratingly affected and overmodulated vocals float over 1984 standard-issue electric piano, and a nation of greasy, awkward seventh graders slow-danced for the very first time.

Worst Moment That power-rock drum fill before the second verse, apparently designed to mollify hatas who thought the band had lost its edge.

17
HAMMER
“Pumps and a Bump” 1994
Next stop: bankruptcy court!

It takes a special kind of awful to destroy a career. This song is that kind of awful. Four years after winning our hearts with his Rick James samples, deft footwork and baggy pants, Hammer (né MC Hammer) took an ill-advised stab at gangsta rap. Over third-rate Dre beats and high-pitched synth samples, the former Saturday-morning cartoon star freestyled about his love of women with gigantic asses. Soon after it nosedived off the charts, Hammer gave up chubby-chasing and devoted his life to Jesus.

Worst Moment The line “You wiggity-wiggity wack if you ain’t got biggity back” must have been found on Sir Mix-a-Lot’s cutting-room floor.

16
4 NON BLONDES
“What’s Up?” 1993

To grunge what “I’d Like to Teach the World to Sing” was to the Woodstock Generation Whenever a new genre comes along, one thing is guaranteed: Sooner or later someone will reduce its values to platitudes, then set them to music so trite you could use it to sell soft drinks. “What’s Up?” stapled grunge angst to the AOR that grunge was supposed to stamp out, then added the remarkable vocals of Linda Perry, a woman so tormented by what she referred to as her “lahf” — which she had apparently spent trying to climb that “heeyuhl of howp” — that she had invented her own accent.

Worst Moment The first chorus, in which Perry unleashes the one thing ’90s rock had lacked to that point: yodeling.

15
THE REMBRANDTS
“I’ll Be There For You” 1995
With friends like these…

Like a support group crammed into a pop ditty, this theme song–turned–radio hit is crushingly sunny, cheaply “empathetic” and unsparingly upbeat. The Beatles-adoring duo harmonize about romantic travails, dead-end jobs and the overwhelming power of — you guessed it — friendship. The only way it could be more irritating is if they repeated “Turn that frown upside down” for three minutes and 10 seconds. It is a powerfully appropriate theme, as it’s impossible to hear a note and not think of Rachel’s haircut, Chandler’s grin, Ross’s whimper.

Worst Moment Four handclaps punctuate the song’s first line, all mimed peppiness and overprescribed Prozac.

14
BETTE MIDLER
“From a Distance” 1990
Satanic ballad depicts the Lord as neglectful oaf

Ignoring an entire century of existentialism and science that declared God dead, bawdy bathhouse babe Bette Midler keeps a straight face throughout liberal homilies, stiff rhymes and more sound F/X than a Mel Gibson movie. Sure, war and famine suck, but Midler assures us that “God is watching us, from a distance.” In other words, the Almighty is some kind of heavenly grandfather, loving and caring, but too doddering and distracted to really get involved. Thanks, God!

Worst Moment The drum machine. If God exists, He probably hates drum machines.

13
GENESIS
“Illegal Alien” 1983
Did nobody ever suggest that this song might be considered a teensy bit…offensive?

The ’80s was the decade when rock superstars like Genesis discovered their social conscience. What better way to draw attention to the plight of illegal Hispanic immigrant workers than by adopting a Speedy Gonzales accent and singing a jaunty AOR track depicting Mexicans as freeloading degenerates? Perhaps fearing that the song’s subtle ethnic humor might be missed by some listeners, Phil Collins sported a Zapata mustache and a sombrero in the video.

Worst Moment The middle eight, featuring hilariously accented shouting of the arriba! and eh, greeengo! variety.

12
THE BEACH BOYS
“Kokomo” 1988
They might as well have just pissed in Brian’s sandbox

The Boys’ Cocktail soundtrack single was their first number 1 since “Good Vibrations” 18 years earlier. But chart position is all the songs have in common. “Good Vibrations” is a glorious slice of Brian Wilson–penned pop perfection; “Kokomo” is a gloopy mess of faux-Carribean musical stylings cowritten by Mike Love. It’s all anodyne harmonizing and forced rhymes (“To Martinique, that Montserrat mystique!”) that would have driven Brian totally nuts had he not been totally nuts already.

Worst Moment The most diabolical rhyme is saved for, um, first: “Aruba, Jamaica, ooh, I wanna take ya!”

11
CLAY AIKEN
“Invisible” 2003
Bad haircut. Worse song!

It’s not just the schmaltzy play for loser pity (“If I was invisible — wait, I already am”). It’s not just the ridiculously purple lyrics. And it’s not just the thought of Aiken’s eternally asymmetrical porcupine ’do quivering as he soars into a high note. It’s the whole hey-girl-I-want-to-watch-you-while-you-think-you’re-alone-in-your-bedroom thing that transforms this song from a merely mediocre ballad to a disturbing voyeur fantasy, filling your head with images of Aiken downloading porn and thinking bad things about that girl from homeroom. What lurks in the hearts of lonely geeks? Clay Aiken knows, and it’s not pretty.

Worst Moment “I wish you could touch me with the colors of your life.”

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.

5
VANILLA ICE
“Ice Ice Baby” 1990
When hip-hop stopped being the “black CNN”

Making fellow early-’90s pop-rap pioneer MC Hammer look cutting-edge by comparison, the chart-topping “Ice Ice Baby” was mindless white rap for mindless white people, set to the plodding bass line from Queen’s “Under Pressure” for easy move-busting. Lyrically, the Iceman recounts a trip to Palm Beach, where he is forced to reach for his “nine” by some moody dope fiends. It later emerged that this nice suburban boy fabricated his tough past and would probably soil himself at the sight of a real gun.

Worst Moment “To the extreme I rock a mic like a vandal/Light up the stage and wax a chump like a candle.” None of this was remotely true.

4
LIMPBIZKIT
“Rollin’” 2000
In which nü-metal veers from disaffected rage to “Will this do?”

Sounding like a middle-aged man trying to fight his way out of his son’s frat party using only random words of youth slang and an unconvincingly gruff tone of voice, Fred Durst dictates a light aerobic workout (“Hands up, now hands down.…Breathe in, now breathe out”) against a background of histrionic metal noise. The song is meaningless and embarrassing in equal measure.

Worst Moment Being addressed as both “partner” and “baby” in Durst’s drawling intro, shortly before being told, bafflingly, “You know what time it is.”

3
WANG CHUNG
“Everybody Have Fun Tonight” 1986
If this song was a party, you’d lock yourself in the bathroom and cry

Initially called Huang Chung, but in no way Chinese, London-based funk tools Wang Chung changed their name to make it easier for whitey to pronounce, thus patronizing Asia and Europe in one stroke. Musically one of history’s least convivial party songs, “Everybody Have Fun Tonight” was both lyrically preposterous (“On the edge of oblivion/All the world is Babylon”) and sung by Jack Hues as though he would turn to sulphur at the very thought of “fun.”

Worst Moment That chorus: “Everybody have fun tonight/Everybody Wang Chung tonight.”

2
BILLY RAY CYRUS
“Achy Breaky Heart” 1992
At least the haircut never caught on. Oh, wait…

Country, but not as we know it. Written by Vietnam vet Don “Pickle Puss” Von Tress in the style of a brain-dead “Blue Suede Shoes,” “Achy Breaky Heart” represented every prejudice non-believers have about country: It was trite, it was inane, it was big in trailer parks and it was thoroughly enjoyed by the obese. Strangely, it was covered by Bruce Springsteen, with slightly less irony than you might imagine; still, this does not make it good.

Worst Moment An instrumental break that single-handedly rejuvenated the line-dancing fad.

1
STARSHIP
“We Built This City” 1985
The truly horrible sound of a band taking the corporate dollar while sneering at those who take the corporate dollar

The lyrics of “We Built This City” appear to restate the importance of the band once known as Jefferson Airplane within San Francisco’s ’60s rock scene. Not so, says former leader Grace Slick, who by 1985 had handed her band to singer Mickey Thomas and a shadowy team of outside songwriters.

“Everybody thought we were talking about San Francisco. We weren’t,” Slick says. “It was written by an Englishman, Bernie Taupin, about Los Angeles in the early ’70s. Nobody was telling the truth!”

Certainly not Starship, who spend the song carrying on as if they invented rock & roll rebellion, while churning out music that encapsulates all that was wrong with rock in the ’80s: Sexless and corporate, it sounds less like a song than something built in a lab by a team of record-company executives.

The result was so awful that years afterward, it seems to bring on a personality disorder in the woman who sang it. “This is not me,” Slick remarks when reminded of the 1985 chart-topper. “Now you’re an actor. It’s the same as Meryl Streep playing Joan of Arc.”

Worst Moment “Who cares, they’re always changing corporation names,” sneers Slick — whose band had changed its name three times.

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