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Ever since Hip-Hop was invented, there have been wack rappers. GQ magazine took note and hooked up a list of the 25 worst rappers of all time in its July 2013 issue.

The men’s fashion mag was liberal with its definition of rapper, though. Some of the names that made the cut include:

#5. Kevin Federline

An ex–backup dancer for Michael Jackson and Justin Timberlake, Federline made the usual boasts about his tax bracket and expensive cars—but his ex-wife, Britney Spears, actually owned everything except the goatee. Real gangstas don’t get $20,000 a month in child support.

#6. Puff Daddy

He’s hit a trifecta: mocked on The Daily Show, on South Park, and in The Onion. Daddy/Diddy has a terrific ear for shameless hooks, and he knows the hustle, which is why he has money hangin’ out the anus, to quote his most memorable lyric. But as a mumbly, indistinct rapper, he wouldn’t be signed to any label he didn’t own.

#12 Prince

If you’re a singer who knocks rappers for being tone-deaf, as Prince did in “Dead on It,” it’s best not to be a singer who’s beat-deaf and raps in a stiff, elementary way, as Prince did in the early 1990s on “My Name Is Prince,” “Days of Wild,” and a few others. Actual couplet: My name is Prince, and I am funky / When it come to funk, I am a junkie. Okay, but when it comes to rap, you are a flunky.

#14 David Bowie & Mickey Rourke

On “Shining Star (Makin’ My Love),” released in 1987, they conjoin their ardor for Burroughs and Bukowski in the worst possible way: Bowie raps about Trotsky and scabs; Rourke answers with some pap about Sinn Féin, Hitler, and fingers in blood. How did this even happen? Bowie had gone crazy because of the international success of “Let’s Dance.” Rourke had gone crazy because he was Mickey Rourke.

#15. Madonna

No matter how incessantly rappers brag, no one has ever before boasted of having three nannies…a gardener and a stylist. The self-mockery in 2003’s “American Life” is banal, and the only other song we know that mentions soy lattes is “Drops of Jupiter” by Train. Both suck.

Too $hort also made the list, and we’re sure at least the Bay Area Hip-Hop massive will not approve.

Read the full 25 Worst Rappers of All Time story right here.

Photo: GQ