Hip-Hop Hooray? The Biggest Rap Fails Of All Time Pt. 1

- By Bossip Staff

lil wayne pants

These rappers made horrible career decisions and we were all there to watch.

From horrible movies to bad endorsement deals, rappers have made bad moves that many people will never forget. You think it’s all about being fly and having bling? Well, sometimes the bad decisions catch up to them. That’s why we’re here! To clown them!

50 cent gq

50 Cent’s GQ Pose- Look at this suspect isht. The wind’s all blowing and he’s got a cutoff dress shirt. What the hell is this? We’re not sure if this is a coincidence or not, but dude’s career has clearly never been the same.

lil wayne rebirth

Lil Wayne’s Rock Album – Yes, Rebirth topped the charts, but as far as being a piece of art, it was pure caca. Besides the Eminem song, it was ear pollution. We were tempted to call Mike Tyson to come bite our ears off.

lil wayne pants

Weezy’s Pants – These things were just inexcusable. He went into the women’s section of the store, said “these are cuuuuute” and threw those joints on?! Are we serious with that right now?

ja rule

Ja Rule’s Acting – DMX wasn’t a bad actor. But Ja Rule? He was barely audible and jumbled. When you act in movies with Steven Seagal, it’s a wrap for the career.

game belly 2

Belly 2 – The first Belly was decent. The second one? That was embarrassing. The Game just rapped about how Hollywood was calling him. Really? They must not have seen Belly 2!


Universal Mind Control – Common is one of the best rappers of all time. However, UMC is easily his worst album. We can blame it on the fact he was distracted by the wonderous cakes of Serena Williams.


Sweatsuit – This wasn’t Nelly’s last album, but it was the one that signalled the beginning of the end. Yeah, he had some love for his country song, but a double album from Nelly is just too damn much.


DMX’s Whole Life Since 2001 – Want a short replay of DMX’s life in the last 10 years? Jail. Coke. Speeding. Jail. Impersonating a cop. Jail. Rant. Coke rant. Jail. Confusion. The end.

dirty money

Dirty Money – Diddy has had a ton of success over the last 15 years. But Dirty Money? His autotuned mash of mediocre songs didn’t exactly set the world on fire. Diddy and the Eastside Girlz hopefully made their first and last album.

black friday

Lil Kim’s Comeback – “Don’t call it a comeback”. Don’t worry. We won’t. Her 2010 campaign was an embarrassment. She should have just given Nicki a coke and a smile and went about her business.

wu tang comic

Wu Tang’s Comic Book – Hip-Hop and comic books don’t exactly go together well. And the Wu-Tang’s comic from the early 2000’s just left us scratching our heads. What, were they going to put ODB in a cape? Get outta here with that.

flavor flav

Flavor Flav’s Rap Album – We know Flav had a rap career in the late 80s and 90s. But his post-reality life solo joint only ruined his legacy. We’d rather watch him and Bridget get their freak on before we listen to this.

gucci mane

Gucci’s Tat – Master P called himself the Ice Cream Man. But Gooch took it to another level. This is the worst tat in rap history. And Lord knows rappers have more than enough tats. Good job, Gucci.


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  • http://idontmakethenews.com Maurice

    Maurice reblogged this on I Don't Make The News.

  • me

    How is Wayne kissing baby not a fail?

  • Brittney

    First off let me say this, as if Gucci aint ugly enough he put a tattoo on his face. More of an #EpicFail…..

    Now…I’m a big Weezy fan always have been but those pants made we want to slap him.

    Kim honey it was good while it lasted. Bow out gracefully like everyone else did mama.

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