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The 25 Worst Rappers Of All-Time

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It's said he who doesn't remember history is doomed to repeat it. Well, how does that explain cable television? Vanilla Ice has a new "Greatest Hits" album just out that redefines both the words "Greatest" and "Hits" simultaneously! That shows more genius than his entire career. But be warned, if you celebrate his banal awfulness, you will only be further rewarded with more of the same. The MC Hammer comeback will spring into full force. Nelly will re-find his magical band-aid and Fred Durst will be given a reason to exist. We need to save the planet now. I don't want to say that ignoring Will Smith can have the same effect on the environment as cutting down greenhouse gas emissions, but what if it turned out to be true?

Here are the 25 Worst Rappers of All-Time. We might have a 26th to add if Bill Cosby gets his act together and releases the "rap" album he threatens!

25) Chicago Bears: The Chicago Bears are a professional football team based in Chicago, Illinois. In 1985, before winning the Super Bowl they daringly commemorated their proud achievement with "The Super Bowl Shuffle," a rap tune that made this group of on the field tough guys look like an ineffective glee club. Did they really psych out their opponents with this? So why didn't they record a follow-up? They didn't win the Super Bowl the next year. Honorable mention goes to the Miami Dolphins, the San Francisco 49ers, the L.A. Raiders, the Cincinnati Bengals and the L.A. Rams, other football teams who couldn't resist the urge to kick back a few beats and look more than a little silly.

24) Bubba Sparxxx: Cut from much of the same cloth as Fred Durst, here's another earnest white boy looking to earn his street cred by exhibiting talents he doesn't actually have. You know how a kid will brag that his TV is bigger than your TV and then never get around to showing you this "Big TV"? That's kind of what a Bubba Sparxxx album is like. You keep hearing about how cool and assured he is, but you never actually hear any music that backs up the claim. Guest appearing on tracks by Limp Bizkit and Justin Timberlake should make you very nervous, despite some legit rappers claiming he's OK.

23) Mike Jones: He can't rap, but he sure knows how to make friends. Putting his cellphone number on his T-Shirts ensured that Mike would never be lonely. But can you really trust a rapper whose track "Houston Dynamo (Don't Play)" is the official team anthem for the Houston Dynamos? A soccer team?

22) Bobby Jimmy And The Critters: In the 1980s, it was only a matter of time before someone decided to parody rap music. Weird Al was slow on the draw here. So this Los Angeles group did the honors with such "timeless" classics as "Gotta Potty," "Ugly Knuckle Butt" and "Somebody Farted." I know it sounds pretty good, classy even, but fart jokes get old quick no matter who's doing the telling.

21) 2 Live Crew: Oh, I know they stand for the first amendment. And "Me So Horny" deserves its rightful place in our cultural lexicon. But take away the historical importance and the one-joke wonder of it all and you're left with a crew of dudes who had to break up before everyone figured out they didn't know what the hell they were doing.

20) Nelly: Whoa, Nelly! Yeah, the band-aid was a great gimmick and noting that when it gets hot, it's man's natural instinct to want to take off his clothes, well, that's priceless, too. Maybe his next album Brass Knuckles, slated for release in a few months, will show us a new side to this flat-screen rapper. Surely, he's had time to find qualified producers and to bone up on his diction to make it sound like something more than reading off of cue cards.

19) Dan Aykroyd And Tom Hanks: Dan Aykroyd at least can claim he's a comedian but Tom Hanks is just an actor who's been cast in comedic roles and worn dresses. "City Of Crime" runs through the credits of their 1987 film Dragnet and they even made a video for it, suggesting they had ideas of branching out beyond their acting community. The hip-hop community apparently didn't welcome them with open arms, saving us from further inept endeavors. They make Rodney Dangerfield, Chevy Chase, Joe Piscopo and Eddie Murphy's rap attempts sound nearly legitimate by comparison. That's going some!

18) Chingy: You know an "artist" is really hitting a nerve when they inspire an onslaught of negative reviews at every website you visit. The consensus seems to be: "This guy's beats are terrible and his lyrics are stupid, degrading and barely literate at best." And we're guessing that came from his mom. I didn't need to read all 385 one star reviews to be tipped off to just how much other people don't admire this man's talent. To think he owns houses in multiple cities, partners a restaurant in Miami and has appeared on The George Lopez Show as himself! Someone's got a bit of explaining to do.

17) Elvira: Cassandra Peterson had a perfectly legitimate career as "Elvira" the devilishly seductive vampire. Had she formed a Goth Metal group, it might have made sense, but in 1988 she opted for "The Elvira Rap," a charmingly inept attempt at doing what she does poorly. But she didn't stop there. "The Monsta' Rap" followed. Fool us once, shame on us. Twice, it's your problem, sista!

16) Insane Clown Posse: Face paint, bad rap-metal, once out of rhymes begin spraying their audiences with soda, Insane Clown Posse have all the hallmarks of a bad hype and the terrible, terrible records to back it up. Violent J and Shaggy 2 Dope don't do much of anything well. Which explains why they hide their true identities. They make Kiss, their obvious influence, seem like the apex of modern culture in comparison. On the bright side, perhaps it's ICP's lame attempts at rap that have stopped Kiss and their accountants from considering a similar move.

15) Rappin' Duke: Any rapper who boasts of working the mic at Ponderosa isn't likely to be taken seriously. His other claim in his self-titled rap 'Rappin' Duke" that Kurtis Blow and Run DMC wouldn't have heard of rap were it not for the "Rappin' Duke" is as ludicrous as his boast that no rapper would exist after him. The Rappin' Duke never had a career beyond this single (there is a second single believe it or not called "The Duke Is Back" on famed Tommy Boy Records, but he apparently was not, in fact, "back"). That's what you get when you choose John Wayne as your point of hip-hop reference. Sorry, partner.

14) Master P: It isn't until you get to the chorus of Master P's Grammy-winning hit "Make 'Em Say Ugh" that you realize just how bad this is going to be. P doesn't show much promise on the verses, but the guttural, food poisoning groan of nausea that provides the tune with its "hook," is among the genre's dumbest and least appealing. He has made a career out of moaning "Ugh."  Of course, this success has been off the chart, ranking him in Forbes as one of the most successful entertainers and entrepreneurs. Thankfully, he now serves as a Youth Ambassador for the NAACP, a move that should lead to fewer musical endeavors. Only God Can Judge Me may be the name of one of his albums, but I prefer to let the people decide this one.

13) Tony Yayo: Being the weakest link in any ensemble brings its own cross to bear. Why do you think Professor Griff was always the most annoyed member of Public Enemy, after all? As a member of G-Unit, Yayo was clearly the caboose of the group. If he really calls his latest album I Am 50's Tax Write-Off, which wouldn't be a bad idea, it would save the IRS time when the audit comes due and blatantly remind everyone he was in a group with 50 Cent. A better idea than Thoughts Of A Predicate Felon. The guy goes to prison on a weapons possession charge, but decides it's better to hype being an Outlaw Of Grammar?

12) Northern State: While some people assume that anyone who can speak can rap, it's not quite that easy. Just as a singer must master pitch and tone, a rapper needs to sound natural. Nothing about this female Long Island trio ever sounds natural. They don't try to pretend they're anything they're not. But being well-educated, literate nerds from Long Island who name-check Al Gore doesn't for convincing rappers make. Grabbing Ad-Rock from the Beastie Boys to produce their album doesn't lend "credibility" either. It looks desperate. And having your tracks featured on Grey's Anatomy is just weird.

11) Shaquille O'Neal: Now I love watching Shaq stand over the basketball net and push the ball in with his hand. Being 12 feet tall has its advantages. Rapping isn't one of them. It doesn't make you sound better. If a midget like the Geto Boys' Bushwick Bill can get it so right, how is it that Shaq could get it so wrong? Well, as Bushwick would tell you "Size Ain't (expletive deleted)." Sure he can wax personal "Biological Didn't Bother" but bad puns like "Can't Stop the Reign" and "Blaq Supaman" (that's not even a pun, that's goofy spelling) just don't quite match up to what he's capable of on the basketball courts.

10) Marky Mark And The Funky Bunch: I believed them when they rapped "I Need Money." That sounded like the truth. But I draw the line when they title an album Music For The People. Why? What did the people ever do to you, Marky Mark? We certainly didn't ask for this music and if we did we should have been more specific. We wanted it to be better, that's for sure. But Marky Mark saw it coming. He knew he had a better career in underwear ads (calling David Beckham!) and in movies. Which is why we don't get to enjoy any new music from him anymore. Somehow, I think we'll make it.

9) K-Fed: When being married to Britney Spears is your greatest artistic accomplishment, you join a long line of Yoko Onos waiting for their eventual artistic validation. Someday, an ironic hip-hop group will no doubt celebrate Playing With Fire, Kevin Earl Federline's debut album. But for now, we're content to pretend it never happened. We'll let him keep custody of his children, but he must promise us to never make another album for as long as he shall live.

8) Will Smith: The people who vote in the Grammy Awards might very well be drunk when they do so. Or maybe they don't listen to the records they vote for. Now rap music wasn't really enjoyed by the "establishment" back in the 1980s, so they were primarily guessing at what the "kids" were listening to. And "Parents Just Don't Understand" was obviously a pretty "wacky" "rebellious" little number with all that clever rhyming! And Will Smith was certainly still "safe" enough to not inspire too much controversy. Which is exactly why he's a lousy rapper. And why Smith got out of there and into acting before everyone caught on.

7) Mr. T: Yes, I pity the fool who thought Mr. T had a career singing, rapping and wearing extremely short camouflage shorts and stretched to the knee tube socks while telling you to treat your mother right. From his instructional video Be Somebody Or Be Somebody's Fool. Why take advice from a guy who seems to have opted for the latter?

6) Fred Durst (Limp Bizkit): You have to question anyone who participates in a group that applauds its own erectile dysfunction. "Rap-metal" sounds like a bad idea, even before you hear how poorly it's executed. Ice-T couldn't pull it off with Body Count and these clowns can't even get the metal part right. So you can only imagine what happens when a rhythmically challenged singer attempts to show his "street cred" by enlisting the help of Method Man, who should've known better than to associate with a group whose stage props have included playing in a toilet. Some hints are more than hints.

5) Puff Daddy: P. Diddy, Puff Daddy, no matter what name you give him, his rapping doesn't improve. Sure, he's been a successful entrepreneur. Apparently, he can sell anything. He sold the idea of talking over a perfectly legitimate hit single by the Police as one of his own creations and winning a Grammy for his troubles. Again, are these people drunk when they vote?

4) Dee Dee King: As the bass player for the Ramones, Dee Dee Ramone was very good at counting off "1-2-3-4" and then playing his bass notes very fast. He didn't sing particularly well, but as a punk rocker he didn't need to. He wrote a handful of great songs. But then he decided he wanted more. He wanted to escape the artistic box that was the Ramones and establish his own identity--as a rapper! We only acknowledge what Dee Dee himself acknowledged. He truly was the "baddest rapper in Whitestone, Queens." R.I.P.

3) Brian Austin Green: Brian Austin Green from the hit TV program Beverly Hills 90210 released a rap album in 1996 with tracks such as "That's Right" featuring the Black Eyed Peas, "Style Iz It," "Didn't Have A Clue" and "Beauty and Da Beats." I believe these titles reflect his passion. And if "sounds great while sleeping in a shopping mall" can be construed as a compliment, then I'm among his biggest fans and--though I hadn't realized it until now--have been anxiously awaiting his "comeback" for 12 years now!

2) MC Hammer: "U Can't Touch This" was first described to me as someone repeatedly yelling "Stop, It's Hammer Time!" over Rick James' "Superfreak." Sounded like a bad idea. Sounded like a bad joke. Then I heard it. MC Hammer went on to sell millions of albums. Some people even took to dressing like him. Yet somehow he never managed to turn this into another marketing line, not even for glasses. That's how he ended up on reality TV, I guess.

1) Vanilla Ice: Whether Suge Knight ever actually dangled Robert Van Winkle, Mr. Vanilla Ice, from a balcony or not, the point intended is an important one: STOP MAKING RAP RECORDS. "Ice Ice Baby" isn't so much a bad song as simply an insult. Instead of making a low-rent porn video, Ice makes Cool As Ice, a film so bad it almost makes you wish he'd stuck to making records.

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