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

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!”