The Top 10 Ugliest Rappers of All Time

July 22, 2009

Since the birth of hip-hop, MCs have always tried to make themselves out to be perfect beings with no flaws in sight. This can be easily achieved on wax with some cocky lyrical content and a nasty hook, but the game kinda changes when you finally get a hard look at the real life mortal being in all their natural glory.

10. Jay-Z

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From the lips to his all-natural prize fighter-like nose, Jay-Z has never been equipped with the dashing good looks he portrays himself as having in his music.

I think the most annoying aspect of Jay has to be his unbelievably large ego. I do understand rappers try to live out the lifestyles that they write about, but this man’s head has gotten a little too big for his Yankees hat in recent years. Dating Beyonce has no doubt added to this self-admiration and his increasing large bankroll is also to blame, but he needs to realize that he’s not as flawless as his apartheid diamond ring. Get over yourself, Mr. Carter. Hot women only date you because you made “Hard Knock Life” and “Big Pimpin’.”

9. ICP

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Even though they always have a ton of makeup on, it’s no mystery that not-so-attractive Detroit dudes reside underneath Violent J and Shaggy 2 Dope’s goofy ICP paint. Although if I am putting these two on this list because of their appearance as rappers, I have no choice but to make my assessment based purely on how they look as hip-hop/rap artists. So with that said, these two are straight up rugged-ass fools. I'm sure they get trim by the truckload, but we can go ahead and assume that J and Dope only have sex with Juggalettes instead of normal women. Have you ever seen a Juggalette by the way? You might as well bang a crackwhore on Skid Row. I can at least guarantee they’ll have better music taste.

8. KRS-One

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The South Bronx native is still one of the greatest MCs ever to do it, but his mug is most definitely a year-long Halloween mask. Luckily for him, he’s never been an LL Cool J-type of performer. Instead of rapping about chasing tail and being a modern day pimp, Lawrence Krishna Parker was off elaborating on the sounds of a beast. I wonder if KRS just puts females into some kind of weird trance by over-elaborating on the specifics of what makes a real hip-hop MC? That has to be the only way he can get a lady back to his NYC abode. 

7. Lil Wayne

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I see comments from women all the time saying how hot Lil Wanye is and I really can’t understand what they are talking about. The guy looks like a midget version of the Predator with really cheesy half-assed tattoos. If girls find this sorta thing attractive I’m totally going to get extensions and some Frankenstein crack tattoos as soon as possible. I’m also considering putting out a really bad Auto-Tuned pop-rock song about some chick I met in high school. Any takers, ladies?

6. Lil' Kim

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Kim wasn’t all that bad looking in her early days with Junior Mafia, but when she decided to overdose on cosmetic surgery and experiment with ridiculous wardrobes, Kim slowly transformed into the real-life extraterrestrial of rap. I’m not totally sure what she’s been going for, but it’s quite clear that Kim has some serious problems expressing facial emotions since going under the knife.

The best part about Kim as an artist has always been her knack for not giving a f***, but I think this may have backfired on her entire face.

5. Lil Jon

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First off, this guy’s full name is Jonathan Mortimer Smith. That’s the first red flag for a serious nerd alert. Have you seen his high school graduation picture? Jon was the biggest dork on planet earth. Lets just go ahead an assume he was a virgin until he got his first record deal. It is nice to see a guy who was once a giant geek go on to make millions of dollars in the rap and tap endless amounts of Grade A trim, though. The guy gives me hope. Yeah!

4. Ol' Dirty Bastard

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I really don’t want to talk too much trash on the not-so-appealing looks of the late Sweet Baby Jesus because we have all seen the cover for Return to the 36 Chambers: The Dirty Version and know why he made the list. The only difference between ODB and some of the other rappers on here is the fact that Dirty knew he was nasty and loved every inch of the funkiness. R.I.P. ODB!

3. Juvenile

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Oh man. The fact that Juvenile has had more sex than me and my entire office combined is a very sad state of affairs. The first time I saw the video for “Back That Ass Up” I was quite perplexed of how this guy was getting all these super-fine girls to drop it like it’s hot on command. I’m guessing selling millions of records has something to do with it because I know there’s no way they’re workin’ him over based on looks alone.

2. Flavor Flav

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You know that revolted sound Sideshow Bob makes when something sh**y occurs on The Simpsons? I make that noise every time I see a picture of Flavor Flav from the last 10 years. I will say that even to this day, Flav is hands down the greatest hype men of all time, but I refuse to recognize a television show that had gang of fine women fighting for the love of a man this unappealing. Look at this guy. He gets more ass than you can imagine in your brain. Not. Fair.

1. Biz Markie

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I love Biz to death, but the guy is truly one the most unsightly rappers ever to spit on a microphone. I don’t care if he was a human beatbox pioneer and one of the true originals of hip-hop, Biz truly hurts the eyes at every single glance. I always remember watching the video for “Just a Friend” and thinking there was no possible way he could have pulled a girl that fine. It pains me to have to tear the guy down, but this list had to be the real deal and Biz’s face has made it so.

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