Wired 25: Nobody’s Perfect – The 25 Biggest Fails From Rap Superstars

We Hip-Hop fans love to mythologize our favorite artists. At the end of the day however, they are just human. They fail just like all of us. 

On this week’s #Wired25, we take a look at some of the biggest fails from the biggest rap stars in the game. If your notoriety is due to your failures, you did not make this list. Charles Hamilton and Papoose, you are welcome.

Nas, Jay-Z, Biggie, Tupac, Wayne, Drake, they are all here. They are all human. They have all failed. Hit the jump to check out this week’s #Wired25, and remember, nobody’s perfect.

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Photo:  Tumblr

25. Lil Kim’s Transformation

Once upon a time, Lil Kim was the most desirable woman in all of Hip-Hop. A few too many trips under the knife later and Biggie’s female protege looks like a cautionary tale for too much plastic surgery. “How Many Licks?” Nah, more like “How Many Trips (to the surgeon)” *rimshot*

24. Yung Berg

Where do you begin with Yung Berg? At one point, he had a promising solo career as an artist after producing many hit records like “S*xy Lady” and “S*xy Can I,” but since then he’s taking more L’s than a Spanish accent. His trademark chain has gone on tour and at one point it seemed like World Star Hip Hop was in existence only to chronicle his many failures. Robbery, drunken shenanigans, getting slapped by Maino and more only begin to tell the story of Berg’s many fails. Since then he’s fell behind the scenes and stuck to producing some pretty hard records. Good choice, kid.

23. Crooked I Gets His Tattoo Misspelled 

Crooked I decided that tattooing his new crews name, Slaughterhouse, was a great idea to solidify the union. Only problem was that his tattooist wasn’t exactly an English major. Make sure you cop “SLAUGTERhouse’s” new album Welcome to: OUR House, in stores now.

22. Prodigy Makes His Debut On The Summer Jam Screen

In hindsight, this isn’t too bad. Everyone was a Michael Jackson fan back in the day, but when Hov dropped the lyrics “You was a ballerina, I got the pictures I seen ya,” along with this picture, the Summer Jam screen was born.

21. Drake Really Likes Working With Lil Wayne

Drake likes working with Lil Wayne. No, he really likes working with Lil Wayne.

20.MC Hammer Busts A Move For Some Fried Chicken

MC Hammer was at one point the most commercially successful rapper on the planet. He got there by selling a bunch of records and hocking a ton of products, including tapping his feet for some fried chicken.

19. Memphis Bleek’s Garnier Fructis Commercial

If this was Bleek’s idea of “Making Easy Money,” then well, we’re good here.

18. Suge Knight Gets Knocked Out By A Barber

Suge Knight was, and in most circles still is, one of the most feared figures in music. But like the old saying goes, the only way to deal with bullies is to punch them in the mouth.

17. Joe Budden Gets Decked, Goes On UStream

People get beat up everyday, that’s not a fail. What is a fail however is going right on UStream moments after it happened and explaining your story with an ice pack on your face.

16. Akon exaggerates his jail experience

Akon broke out with his hit song “Locked Up,” in which he claimed to be running a ring of car thieves and serving four years in prison.

The truth was that he was arrested in 1998 for possession of a stolen BMW, the case was subsequently dropped by a Georgia court. He has been arrested on other occasions, but the stiffest sentence he has faced was three years’ probation for gun possession. Since then, he’s made millions of dollars on his own and having a heavy hand in the success of Lady Gaga. Jokes on us, huh? 

15. “Voting Good” – Waka Flocka Flame

Terrance J and Rocsi, formerly of 106 & Park, thought it would be a good idea to spring up congressional voting in the middle of Waka Flocka Flame’s press run. Poor Flocker didn’t know what hit him.

14. Lupe Fiasco Forgets Lyrics During A Tribe Called Quest Tribute

Lupe Fiasco, Common and Pharrell were tapped to do a special tribute performance to honor the legendary A Tribe Called Quest. Lupe hit the stage and famously flubbed the lyrics to the ire of tons of Quest fans. If it wasn’t for Busta Rhymes’ epic rah-rah performance, this might have been an even bigger deal.

13. Lauryn Hill Gets Booed On Apollo At 13 Years Old

Lauryn Hill crafted one of the greatest works in the history of pop music with The Miseducation Of Lauryn Hill. More than a decade before that, however, she was just a little girl from Jersey trying to do her thing at the Apollo. It didn’t go too well.

12. Jay-Z Tries To Kill Off Timbs, Fails

Jay-Z is a businessman, trendsetter, and by most accounts the greatest rapper of all time. It doesn’t mean he didn’t catch his share of fails. In his song off The Blueprint 3, he tried to kill off Timberland Boots in the song “Off That.” A Brooklyn cat, trying to say we are off Timbs? That’s damn near blasphemous. Thankfully, Hov came back to his senses.

11. Jim Jones and Cam’Ron Get Jumped At Rucker Park

The Diplomats had one of the greatest runs in the history of Hip-Hop. However, this melee that occurred at Harlem’s Rucker Park, and documented by TNT’s cameras, featured Jimmy and Killa getting ran down in their own backyard.

10.Young Buck Cries To 50 Cent

If you didn’t think 50 Cent was ruthless before, this definitely solidified it. After Young Buck allegedly dissed 50 Cent, he released this audio of the Tennessee rapper sobbing to his boss. It’s okay, Buck. We all get confused.

9. Canibus Pulls Out A Notepad During A Rap Battle

Canibus, the same guy who actually went toe-to-toe with one of the greatest of all time, was losing a battle to seasoned veteran Dizaster. What was his last line of defense? Pull out a giant notepad and spit those bars, kid. This is painful to watch.

8. The Game Gets Curved On “Change Of Heart”

Before he was Game, he was plain ole JT. Mildy popular dating show, Change Of Heart, featured Game as a guest on the show which features a couple going on separate dates. After the dates, the couple decide if they want to stay together or have a “change of heart.”

7. Drake Tears ACL on stage

Drake Mania was something to behold once upon a time. The former child star was still pretty green on the stage and was joining Lil Wayne on stage to manic crowds. In this epic performance, art imitated life as the MC hit the stage too soon after injuring himself playing basketball and re-injured the leg. Ouch.

 6. Tupac’s Fun With Bubbles

Polling most rap fans, Tupac is on the short list of the greatest rappers to ever live. However, this shoot with David La Chappelle featured the rapper who lived by Thug Life dipped in soapsuds and gazing into the camera. And this is the shot we were allowed to use on the site. Trust me, it got worse.

5. Dr. Dre’s World Class Wrecking Crew Days

Undoubtedly the architect of Gangsta Rap, Dr. Dre is the most influential producer in Hip-Hop history. But before he came “Straight Outta Compton” to tell us “F**k The Police,” he was happy go lucky Andre Young from the World Class Wrecking Crew. One time for the jazz hands.

4. “I’m the only one he kiss on the mouth” – Lil Wayne

This just…defies explanation. Just watch the video.

3. William Roberts: Correctional Officer

Rick Ross is one of the most infamous drug dealers to ever live, making millions upon millions of dollars by selling cocaine and other drugs. William Roberts is a former correctional officer who is now one of the most successful rappers in the game today. Trust us folks, it still doesn’t make much sense to us neither.

2. “She looked so good, I’d suck on her daddy’s d**k.” – The Notorious B.I.G.

The Notorious B.I.G. is by most accounts, the greatest rapper to ever live. Lightning in a bottle, his life was cut short due to violence and passed on before he even had the chance to make wack music. Now questionable lyrics? That’s different. The lyrical genius that was Christopher Wallace once uttered that a woman looked so good to him, that he wanted to “suck on her daddy’s d**k.” Dude, what?

1. NaS

Nas’ career is a real conundrum. For as respected and prolific a lyricist he is, his personal life has taken so many losses it became comical. He won a battle with Jay-Z, but lost the war by signing to him at Def Jam. He divorced Kelis, who made a killing off of him in court. There was this. He’s had the mother of his children splacked out by Hov and Allen Iverson, and just more and more epic L’s. Thank God, he can rap his a** off.