10 Of The Most Embarrassing Rappers Of All Time

Rap, like all genres of music, has lots of fans and lots of critics. There are some who are die-hard hip-hop fans and see the music as one of the industry’s truest art forms. Others feel that rap does

Rap, like all genres of music, has lots of fans and lots of critics. There are some who are die-hard hip-hop fans and see the music as one of the industry’s truest art forms. Others feel that rap doesn’t have any real musical value, mainly because they can’t understand the lyrics. Then there are others who had an affinity with rap in previous years, but aren’t impressed with the rap music that has been released recently.

Just like the overall preference for rap music is debatable, so are the rappers. Some rappers are seen as the best in the genre, while others are viewed as completely terrible when it comes to rapping skills. Of course, there are a few rappers that should never release another album, and most people agree on who those rappers are.

Don’t get us wrong. Some of these rappers are entertaining, just not when they’re rapping. It’s also important to point out that some of these artists are more well-known for public scandals and other sources of embarrassment, than they are for being rappers. That’s just sad, and it’s a sign that these people should probably look into new careers. Fortunately, some of them have.

10 Sean Combs

Sean Combs (aka Puffy, aka Puff, aka Puff Daddy, aka P. Diddy, aka Diddy) is a talented businessman and producer. He’s great at finding music talent and helping to put together albums for noted rap artists and R&B singers. After all, he worked with The Notorious B.I.G. (aka Biggie aka Biggie Smalls), who is still considered one of the greatest rappers of all time, even though he passed away in 1997. Combs also gave people like Lil’ Kim, Faith Evans and Mary J. Blige their start. More recently, he was behind the groups Danity Kane and Dirty Money. It’s just that, as a rapper, Combs leaves a lot to be desired. He makes a pretty good hype-man, though (his occasional “yeahs” and “uh huhs” usually make a song more interesting). However, hearing a whole verse from Sean Combs tends to make you wish he’d just go back to producing songs, or making more Ciroc or designing clothes or something.

9 Petey Pablo

Petey Pablo, a native of North Carolina, allegedly got signed to Jive Records after the A&R of the company heard him rapping in the bathroom. That’s probably not the best place to determine whether or not someone has the skills to be a rapper. His first single, Raise Up was produced by Timbaland and hit the airwaves in 2001. It got a lot of radio play and was often featured on MTV, mainly for its feel-good, party vibe. It doesn’t hurt that Timbaland was connected with the record, either. Pablo even received a Grammy nomination for Best Rap Album in 2003. That same year, he’d released the single Freek-A-Leek, produced by Lil John. Judging from the title of the song, it was pretty safe to assume this wasn’t going to be extremely high-quality music. In 2004, he was featured on Ciara’s debut single Goodies. He then went on a hiatus and released a mixtape on his independent label in 2012. Pablo also appeared in two movies: Drumline (2002) and Just Another Day (2009). His gritty voice and eyebrow-raising lyrics may be enough to grab your attention for a few seconds, but entire Petey Pablo albums just seem like too much to bear.

8 Chingy

Chingy is a handsome rapper from St. Louis whose regional accent was very apparent in his debut single Right Thurr. In the summer of 2002, he toured with fellow St. Louis rapper Nelly, and was later signed to Ludacris’ Disturbing Tha Peace label. While Chingy definitely came across as charming, his lyrics leave a lot to be desired. He went on to release the singles Pullin’ Me Back and Dem Jeans, which both indicated that he should probably spend a little more time writing his songs before recording. His most recent album, called Success & Failure, was released in 2010. It’s likely you’ve never heard of it. Enough said.

7 Lil Jon

In the early and mid 2000s, it was pretty hard to listen to a rap song that didn’t feature a harsh voice piercing though the music with one-word phrases like “yeah,” “OK,” or “what.” That was the voice of Lil Jon, who is a Grammy Award-winning artist. Lil Jon has also produced a number of records and has worked with fellow Atlanta artists Ludacris and Usher to make most of the music you heard at parties if you were in college between the years of 2000 and 2006 (roughly). Lil Jon’s voice was catchy, but hearing an entire song of him rapping is easily irritating. Besides, his lyrical content is simple at best. These days, he’s taken the hint that rapping is not for him, and has a standing gig as a deejay in Las Vegas. We think that’s a wise choice.

6 Master P

Percy Miller, also known as Master P, grew up in poverty in a housing project in New Orleans. He didn’t let his environment stop him from reaching his dreams and achieving financial success. For that, he is certainly to be admired. However, as a rapper, Master P has very little talent. Miller is best known for his single Bout It, Bout It and for starting his own label, No Limit Records. A number of his early songs talked about the hardship of ghetto life, and many of the lyrics were vile, crass, and deficient in creativity. His son, Romeo Miller, is also a rapper, and is just a little better than his father. It’s safe to say that most people would rather see Romeo on the small screen (he’s been in a number of television shows and TV movies). Master P should stay behind the scenes and give his son and daughter Cymphonique (who is also an actor and singer), advice about the business to increase their chances of success.

5 Gucci Mane

Gucci Mane came on the scene in 2005 with his album Trap House. He followed up the single Hard to Kill in 2006. He also released Trap-A-Thon and Back To The Trap House in 2007. So apparently, Gucci Mane likes to rap about “traps,” which are old abandoned homes in neighborhoods that are often used as drug houses. This gives the listener a pretty good idea of the content that Gucci Mane delivers to his listeners. His voice can get annoying, and he decided to get an ice cream cone tattooed on his face. That’s a pretty clear sign that he can’t be trusted to make sound artistic choices.

4 Rich Homie Quan

Rich Homie Quan is one of these rappers who also likes to sing. This would be fine, except he can’t sing. The Atlanta rapper is best known for his singles Type of Way, Walk Thru and Flex (Ooh, Ooh, Ooh). He is also featured on the single Lifestyle, by Rich Gang. Even though he was included in the “freshman class” of XXL Magazine in 2014, it’s hard to find a song by Rich Homie Quan that has any real substance. His lyrics aren’t particularly intelligent, but at least (some of) his hooks are (somewhat) catchy. It’s a shame his baseball career didn’t pan out after he played in high school and wanted to go pro. Perhaps that would have been a better career choice.

3 Chief Keef

Chief Keef is a rapper and record producer from Chicago. To be fair, there’s a slight chance that he may be a decent rapper, but it’s so hard to understand anything that he’s saying when he raps. He started becoming famous when he was under house arrest, and there was a bit of a bidding war when he was deciding whether to sign with a label. He finally decided to sign with Interscope in 2012, but was dropped in 2014 due to his constant legal issues. His debut album Finally Rich, was released in 2012 and was met with anticipation by rap fans. But his lackluster lyrics and strange enunciation were disappointing at best. After Chief Keef was dropped from Interscope, he started his own record label Glo Gang, and started releasing his own mixtapes.

2 Birdman

The New Orleans rapper and producer has been in the music industry for years, but isn’t showing any signs of improvement when it comes to his rapping skills. After all, if you’re going to continue rapping as a middle-aged man, the least you could do is rap about social issues or substantial relationships. Instead, it looks like Birdman still wants to let the world know how much money he has and how many cars he owns. He’s obviously committed to being a rapper, because he has several tattoos on his face, and we don’t know of too many other jobs where that would be acceptable.

1 Vanilla Ice

We have to admit, back in the 1990s, Vanilla Ice did make us “stop and listen” when he released the song Ice Ice Baby. However, after this hit single, Vanilla Ice never quite achieved big success as a rapper. Also, if you really listen to the lyrics of Ice Ice Baby, you have to admit that the lyrics weren’t all that great. However, the song was an undeniable hit, and caught the eye of some big hip-hop executives, namely Suge Knight. Allegedly, Knight threatened to throw Vanilla Ice off a hotel balcony if he didn’t give up the rights to the song. Vanilla Ice took a long hiatus from music, but his stepfather persuaded him to start working on his passion again in the early 2000s. In 2009, Vanilla Ice signed a deal with StandBy Records, but later left the label. More recently, he joined New Kids on The Block and Boyz II Men on their tour. Maybe it’s best that Vanilla Ice simply show up occasionally for the sake of nostalgia, and not try to make any more new music.


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10 Of The Most Embarrassing Rappers Of All Time