GQ Names The 25 Worst Rappers Of All Time


List After The Jump


Lists of the best and worst artists of any genre of music are generally hard to make. There are obvious choices for either category, then there's the gray area where depending on what region of the country you're from could sway your opinion one way or another.


GQ has put a list together of the 25 worst rappers of all time. Most of them are dead on, but a couple may leave you scratching your head. Peep the list below.


25. Tom Green


Confession: We've never heard 2005's released-only-in-Canada CD Prepare For Impact. If he wanted it released outside of Canada, he shouldn't have titled a song "Don't Mess With A Man (After He Takes A Big Poo Poo)."

24. MC Skat Cat


A cartoon feline who rapped on Paula Abdul's 1989 hit "Opposites Attract," then "went solo," with voiceovers done by a Minneapolis radio deejay. As discriminating a judge as Abdul was on American Idol, as good a singer as Abdul was on "Opposites Attract"—that was the level of Skat Kat's rhyming.

23. Chingy


After Nelly brought St. Louis lingo to the masses, Chingy appeared in 2003 with a debut that made his STL roots obvious: "He's Herre," "Right Thurr," and "Wurrs My Cash." His commercial pizazz faded as his good-time topics (sex, money, having sex with girls who like his money) stayed the same, and he titled his fourth album Hate It or Love It, which turned out to be an easy choice. On the other hand, if you get a good laugh out of "That's me, Ching-a-ling, equipped with much ding-a-ling," you might object to his inclusion here.

22. Joaquin Phoenix


It was all a hoax, a meta-commentary on celebrity culture that played out like the worst RISD freshman project ever: in 2009, Phoenix announced his retirement from acting to start a "rap career," rhymed badly on a Vegas stage and then fell off of it, and went on David Letterman's show looking like a Hasidic version of pre-death Jim Morrison. A year later, he released his mockumentary I'm Still Here, which flopped, proving again that old saw: Jokes are better when they're funny.

21. Too $hort


Not even Too $hort will be surprised to see Too $hort's name on this list. "Serious hip-hop fans, they'll boldly say, 'Too $hort ain't the best, Too $hort ain't got the best lyrics,'" he admits. This pioneer of Bay Area hip-hop has had an unusually long career—even he's lost track of how many records he's done—most of it pedestrian. He has no interest in being "a rapper who rapped in metaphors, and said slick s***," he declares, which is kind of like a NASCAR driver saying he doesn't want to drive fast.

20. Will Smith


At this point, he'd duet with Frank the Pug if he thought it would sell a few extra movie tickets.

19. Pro athletes, post 1985



When the Chicago Bears made the (Grammy-nominated!) "Super Bowl Shuffle," it paved the way for other over-indulged jocks to rhyme at sub-amateur levels. Take the Lakers' Ron Artest, whose idea of gangsta was starting beef with silver-haired, bespectacled David Stern and Matt Lauer ("You look like a girl"). One jock we'll exempt: Shaq, for his "Kobe, tell me how my a** tastes" freestyle.

18. Soulja Boy


In "Pretty Boy Swag," Soulja Boy repeats the song title, with the same dead inflection, thirty-six times. By reducing hip-hop to chants, ringtone beats, and vapid boasting, he has inspired a notable generation gap: everyone over 25 seems to hate him, from LeBron James to Ice-T, who accused him of "single-handedly killing hip-hop." Because ganging up on somebody is always wrong, and because we're equally capable of killing hip-hop, we've written about half of a song for Soulja Boy: "Man I look pretty / Your mama's a** is s***** / Gonna buy a big watch and wear it 'round the city." The more times you say it, the better it sounds!

17. Weed carriers (St. Lunatics, Bravehearts, D-12)


Once rappers become stars, they have the leverage to drag friends along with them into prosperity. They also need someone to transport weed, a job that dates back at least to "Spanish Tony" Sanchez, who was Keith Richards' personal drug mule. "Weed carrier" (aka baggage handler, tree stasher, or weed wallet) is the unflattering term to describe rappers who perhaps might not have record deals if an influential friend hadn't demanded it: The Bravehearts, St. Lunatics, and D-12.

16. Brian Wilson


"Smart Girls" is not well known because it's from an album, aptly titled Sweet Insanity, which was never released, but the circa-1990 track is easily found on YouTube. "My name is Brian and I'm the man / I write hit songs with a wave of my hand," he begins. Then it gets worse, as samples from old Beach Boys songs fly in without warning. Wilson's rapping is on par with Biz Markie's singing.


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.

14. David Bowie and 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.

13. Master P


When people praise Master P, it's usually for his bootstrap entrepreneurship: he rose from one of New Orleans' most despairing housing projects into a self-described "ghetto Bill Gates," though unlike the man born Percy Miller, Gates never branched into sports management, films, clothes, or phone sex. Master P was notorious for ostentation, including 22-carat-gold panels on his bedroom ceiling. (His net worth was once estimated at $361 million; four years later, he filed for bankruptcy.). But songs are virtually interchangeable, he's often accused of jacking ideas from other rappers, his lyrical signature is a constipated grunt (Uhhhhhh!), and in a Fortune magazine profile, a competing rap executive described P's record label as the "McDonald's of hip-hop," though to be fair, he appeared to mean it as a compliment.

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.

11. Eazy E


He had some malevolently funny lines (I'm Eazy E, and I got b****** galore / You might have a lot of b******, but I got much more), but they were usually written by Ice Cube, who said it took "days" for Eazy to clumsily record his snaps. ("I can't do this s***," Eazy complained when asked to rhyme.) A small man—Cube called him a half-pint b****, and Snoop referred to him as Tattoo—with a voice pitched midway between Geddy Lee and Fran Drescher, he was a one-dimensional gasbag with the rhythmic grace of a dot-matrix printer.

10. The two guys in the Black Eyed Peas who aren't


Will produces the songs. Fergie sings the hooks. You do...what exactly?

9. Pitbull


A Cuban-American Vanilla Ice who flacks for Dr Pepper and Bud Light—try mixing those two for a fun speedball!—Pitbull specializes in mind-numbing Eurodisco about hot girls and nightlife, with witless, winking reminders of his heritage: My tongue is bilingual, ready to play with that spot where you tingle.

8. Everyone from England, ever


With one exception: Mike Skinner of the Streets.

7. MC Hammer

When people remember you more for your pants than your lyrics, it's a bad sign.

6.  Diddy


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 a***, to quote his most memorable lyric. But as a mumbly, indistinct rapper, he wouldn't be signed to any label he didn't own.

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.

4. Vanilla Ice


History's first truly awful rapper—like Richard Nixon, he sullied an entire occupation with unprecedented terribleness. Unlike Nixon, he won't go away: He made a metal album, went on reality shows, and re-recorded "Ice Ice Baby" along with nine other "hip-hop classics." You should hear what he does to Public Enemy.

3. Chet Haze


Tom Hanks's son Chester—a Dollar Tree version of Justin Timberlake—hit the rap game in 2010 with a series of YouTube videos. In one, he raps about Glocks and bling, threatens to stab you with a ski pole in yuh peep hole and warns, Step to me, get beat down like Rodney King, which is an odd way for a white guy to express solidarity with black culture.

2. Spencer Pratt


"I don't have to have talent," this talentless yet conceited reality-TV addict once said, celebrating his appalling rap bow, "I'm a Celebrity." Pratt's flow is sick—he rhymes like he has Parkinson's. He called himself "the white Jay-Z," possibly because they both have opposable thumbs, and notably bragged on "I'm a Celebrity" that MTV made me president rich. The next year, he reportedly filed for bankruptcy.

1. Insane Clown Posse


The KISS-style makeup these two self-anointed "wicked clowns" wear is a tip-off—they live to sell peripheral products, from DVDs to comic books to PPV wrestling cameos, to the tune of millions of dollars annually. Like most d-bags, they're predictable: Ample use of the words f***psycho, and f*** attracts a devoted fan-clan, and their annual festival has also included, yep, Vanilla Ice.       


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Comment by TONY on July 15, 2013 at 12:26pm

Half of those aren't even rappers. smfh

Comment by iCarmelo on July 15, 2013 at 11:37am
This list is horrible they really put eazy e and too short on this list? And diddy isn't terrible he had some classic songs with big.. Smh at the disrespwct
Comment by D Nate on July 14, 2013 at 8:51pm

where is french montana?

Comment by SonGetWrec on July 12, 2013 at 12:55pm

#1 should be a tie between ICP and Eminem.

Comment by Young Gunner on July 12, 2013 at 12:50pm

@D.Money Not trying to b**** about Americans as most of my favourite rappers are American but there are some good UK ones.

Comment by egie on July 12, 2013 at 8:51am

no diidy

Comment by J-Byrd on July 11, 2013 at 11:58am

f*** this list

Comment by TimEpke15 on July 11, 2013 at 6:43am
You guys forgot Lil Wayne
Comment by Isiah on July 10, 2013 at 7:29pm

This list is whack stick to fashion.

Comment by Rap Satan on July 10, 2013 at 6:03pm

where's lil b?

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