Top 10 ugliest rappers of all time - #1 will leave you in stitches! (With Pictures) | Page 10 of 10

Ugliest rappers of all time - When it comes to the traditional ideal man as “tall, dark, and handsome”, most rappers do not fit the bill. However, what they don’t deliver in looks, they can always make up for with their money. Luckily for these rappers, they can get in a studio and deliver music which reaches the ears of millions before it reaches their eyes. More..

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To kick off the list is Public Enemy’s very own, Flavor Flav. Flavor Flav has been credited as being so unattractive that Comedy Central even dedicated a roast to him in 2007 when comedians all took turns making fun of the rapper. During the roast, comedian Jimmy Kimmel took a jab at Flav saying: “Flav, I don’t know how old you are but you don’t look good. When I first saw you sitting up there, I thought it was an open casket memorial for James Brown”. Ouch! But don’t let the ugly looks deceive you. Long after he was “fighting the power”, he had ladies lined up literally fighting for his love when he debuted his reality show, Flavor of Love. The love for Flav was so real, he garnered a total of 3 seasons; all of which had dozens of women falling in love with his…ummm charm? 9. Jay-Z

Jay-Z is undeniably one of the best rappers alive. However, if it weren’t for his street smarts and business mindset, his looks alone may not have brought him nearly the amount of success he has today. It’s no secret he has distinct features which have been nitpicked by celebrities such as Amanda Bynes, Nas, and Cam’ron; yet Jay-Z gets the last laugh while being married to one of the most beautiful women in the world. 8. KRS-One

Even one of the greatest attributes to hip-hop isn’t safe. KRS-One comes in at number eight as one of the ugliest rappers. His nose may be big but so are his records. This hip-hop legend has several awards under his belt including a VH1 Hip-Hop Honors award. They say that beauty comes from within and KRS-One proves this to be very true. in 1989, he formed the Stop The Violence Movement as an initiative to stop violence in the black community. 7. Lil Wayne

Lil Wayne has proclaimed himself as the “greatest rapper alive” and with confidence that high, he probably couldn’t care less about his looks. On a segment of ‘Mean Tweets’ on Jimmy Kimmel Live , the rapper read out-loud an unfiltered Tweet which read “Lil Wayne looks like a crabapple”. But don’t let the looks fool you, Lil Wayne has dated some of the hottest women in Hollywood such as Lauren London and Christina Milian. Wayne has even admitted he lost his virginity at the tender age of 11 while playing board games with a girl two years older than him. 6. Mannie Fresh

Reigning right behind number seven and former colleague Lil Wayne, is Mannie Fresh. Mannie Fresh has been the butt of several social media jokes with people claiming he resembles the ever beloved Winnie The Pooh. But just like Winnie The Pooh, Mannie Fresh probably has no problem getting all of the honeys, by rapping lyrics suggesting that everything he owns is, well, “Real Big”. We can’t argue with that one. 5. Coolio

“Gangsta’s Paradise” rapper Coolio comes in at number five on our list. Since making his debut in 1994, Coolio’s braids seem to now be holding on for dear life. Whoever his stylist is really needs to inform the rapper that a bald head and braids just don’t look good together (and probably never will). Apparently, the ladies have never minded his crazy hairstyle because he has a total of ten children from four different relationships! 4. Biz-Markie

Given his looks, it does not come as a surprise that the girl Biz Markie rapped about in “Just a Friend” was simply not feeling him, however, the rapper knows he lacks in the looks department. In 1993, he released All Samples Cleared! . On the album was one track in particular titled “I’m An Ugly N***** (So What)”. In the song the rapper says: Back in the days, I’m not gonna lie They used to say I’m ugly, a hurting guy They would crack on my lips, and my powder Given his track record, he has done pretty well without the help of good lucks. He has toured with Nickelodeon’s Yo Gabba Gabba and appeared on several episodes of Hip Hop Squares . 3. Benzino

Rapper and CEO of Hip Hop Weekly Magazine, Benzinocomes in at number three on our list. When Love and Hip-Hop Atlanta first aired, viewers couldn’t help but talk about his neck. His face became the center of memes which circulated all over social media. In typical Twitter fashion, one user even found a picture of a dog which oddly resembles him. But when you have a beautiful fiance like his, we can all agree that looks are rather irrelevant. 2. Lil Jon

The King of Crunk, aka Lil Jon, comes in at number two on our list. There are several rumors as to why we don’t see him without his glasses. Some say he is sponsored to wear them while others say he is severely cross-eyed. Whatever the case may be, Lil Jon has undoubtedly turned up airwaves and produced some of the biggest club songs to date. It is alleged that he is set to release a 7th album Crunk Metal in this year. 1. Young Thug <div class="responsiveImg img_article_content_new" data-alt="via rollingstone.com" data-src-base="http://static3.therichestimages.com/" data-size="0:cdn/320/179/90/cw/,481:cdn/450/253/90/cw/,768:cdn/736/413/90/cw/,1024:cdn/568/319/90/cw/,1240:cdn/780/438/90/cw/,1400:cdn/1000/562/90/cw/" data-size2x="0:cdn/480/269/90/cw/,481:cdn/675/379/90/cw/,768:cdn/1104/620/90/cw/,1024:cdn/852/479/90/cw/,1240:cdn/1170/658/90/cw/,1400:cdn/1401/788/90/cw/" data-image="wp-content/uploads/2016/03/1401x788-GettyImages-470213082.jpg" data-viewport="1366">

He’s different and embraces it. Coming in at number one is rapper Young Thug. He’s even stated in an interview that he is aware of all the things people say about him: “I like everything that people say,” he continued: “No matter what they say. You ***, you a punk. You got a nice girlfriend, you’re ugly, you can’t rap, you’re the hardest.” Regardless of his haters, Young Thug continues to make music and top radio airwaves. He recently released his latest mixtape Slime Season 3 which has overall received positive reviews. Despite what people say, between his growing net worth and beautiful fiance, Young Thug is undoubtedly winning. Sources: rollingstone.com , therichest.com CLICK HERE to join our BBM Channel for faster updates