The 50 Worst Hip-Hop Fails

The struggle is real.

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Complex Original

Image via Complex Original

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A refresher course in physics: Isaac Newton found that for every action, there is an equal and opposite reaction. In hip-hop—a culture that celebrates its ability to test the boundaries of exaggeration—the highs go unbelievably high: Bitches, riches, and speedboat motorcades are the norm. That being said, when some of these rappers crash, it's a hard fall and piles of pennies don't act as a solid cushion. There's a thin line between champagne showers and golden showers.

And, these days, urban legends are no longer relegated to barber shops and tin-can alleys. With the Internet in overdrive, every day is an obstacle course in new media: Regrettable interviews can happen at any time, and opinions are formed immediately. Everyone's suddenly got a voice, and anyone's volume can be turned up to 11. Today's poster child might wake up as tomorrow's Twitter hashtag, as long as there's the right Flipcam footage or screenshot. And that fail will never go away, cached somewhere in the annals of your favorite hip-hop blog. If there's one thing we've learned, it's that nothing dies on the web...except for careers. Complex looks back on all the bad moves and hilarious humiliations from rap history in our countdown of The 50 Worst Hip-Hop Fails.

This story originally appeared in altered form on June 17, 2010

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Written by Jeff Rosenthal (of @ItsTheReal)

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50. Drake Re-Injures Himself While Skipping On Stage

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Fail Occurred: 8/1/2009

What gets to the floor faster than a Young Money groupie? Drake, while dancing onstage. He'd already injured his ACL during a game of pick-up basketball, which had made his live performances lame. He'd become a stool-bound puppet on the side of the stage. Against the wishes of his doctors, Drake decided that—while performing for a cheering New Jersey audience—he would test his limits. It was a good idea until it became a terrible idea, which was when his knee buckled and he fell face-first into the ground.

49. DJ Green Lantern Talks About 50 Cent Behind His Back

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Fail Occurred: 5/6/2005

50 Cent isn't the most forgiving person. His hit list includes enemies first, but their friends right behind. When Jadakiss joined Ja Rule on "New York," 50 moved Jada to the front of the line. It was a typical back-and-forth war of words until Jadakiss was doing an interview with street DVD The Come Up. When he put Eminem's tour DJ-an unknowing Green Lantern-on speakerphone, cameras caught him spurring on Team Jadakiss: "That's a jab. Where's a knockout?" Yikes! Green, in an attempt to defuse the situation, stepped off of Eminem's tour and away from his show on Eminem's satellite radio station, Shade 45. All parties have made up since.

48. Roxanne Shanté Lies About Free Ride To College

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47. Game Gets Dumped On "Change Of Heart"

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Fail Occurred: 10/19/2006

On many of his songs, Game tries to paint himself as an icy gangbanger, a Blood without a pulse. When TMZ released this 2000 video of a pre-Game Jayceon Taylor on daytime game show Change of Heart, it showed a very, very different side to the rapper. "I break my back for you!" he said. She said, "He tries to act really macho, but he's not. He's really sensitive!" In the end, he opens his heart to her, and gets rejected for all to see. It's a storyline that would be repeated later with Game and 50 Cent, then Dr. Dre, and most recently with Interscope's label boss Jimmy Iovine casting him aside. Somebody give the poor guy a hug.

46. Canibus Performs On The VMAs In Silver Body Paint

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45. Lupe Fiasco Calls Obama "The Biggest Terrorist"

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44. Tru-Life's MySpace Gets Hacked By Dipset

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43. Hieroglyphics Gets Served By Saafir On The Wake Up Show

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Fail Occurred: 11/28/1994

Long before Jay would put Prodigy up on that Summer Jam screen, Oakland rappers Saafir and the Hobo Junction similarly emasculated Hieroglyphics crew members Souls of Mischief and (former friend) Casual in a storied freestyle battle on Sway & Tech's Wake Up Show. During the hour-long melee, in which Saafir was accused of using writtens, he thoroughly pulled the Souls' members cards, exposing their upper-middle class roots and friendships with "Buffy and Brad." While the battle itself didn't end any careers, it did seem to send Souls of Mischief into a creative spiral. The foursome struggled to assert their "street" cred on their soon-to-come sophomore LP, No Man's Land, opting for heavier Bay accents, regional production, and harder subject matter. Unfortunately... (*wait for it*) That's when ya lost!

42. Memphis Bleek Does A Shampoo Commercial

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Fail Occurred: 8/1/2008

On the remix to Kanye West's "Diamonds are Forever," Jay-Z promised that Memphis Bleek would never have to worry about money-that he's in Jay-Z's will, promising his childhood friend and du-rag-wearing compatriot an island "to kick back and chill somewhere." So, one wonders just why Bleek pops into frame during this shampoo commercial to spit bricks like, "Garnier, it strong all day/It replenish your glow." Maybe Bleek was just getting a head start on the recession, a month before the bottom fell out of Wall Street.

41. M.O.P. Makes A Song With LFO

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Fail Occurred: 6/26/2001
Having built their career on aggressively underground and elbows-out aggression, M.O.P. would be an odd fit for any pop collaboration. Crooning à la 98 Degrees? That's not what the Mash Out Posse does. Which is what made "Life Is Good," their collaboration with the Lyte Funky Ones on the Dr. Doolittle 2 soundtrack, so strange. If 98 Degrees was the bootleg Backstreet Boys, then LFO was truly the bottom of the boy-band barrel, the type of cornballs that Justin Timberlake probably clowned while getting his tips frosted. Over a track that would seemed like Sugar Ray-lite (as if that were possible), M.O.P. member Billy Danze yells, "It's hard to sleep at night with a guilty conscience." Wonder how he's sleeping now.

40. Scott Storch Releases A Hardcore Timbaland Diss Video

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Fail Occurred: 2/26/2007

When Timbaland released his single "Give It 2 Me," he enlisted the help of Justin Timberlake and Nelly Furtado. The premise? The three each dissed their most prominent "haters," with Timbaland sending veiled shots at Scott Storch. Well, maybe not-so-veiled: "I'm a producer, you just a piano man." The normally low-profile, non-rappin' Storch didn't appreciate the shout-out, and recorded his own song, "Built Like That." It's three minutes of (terrible) cocaine raps, though not because he sounds like Young Jeezy or the Clipse; more for the fact that he was abusing cocaine at the time. And the video? Wow. Let's just say that Scott is better when he's sitting behind a piano.

39. Chopper Introduces The Chopper Suit

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Fail Occurred: 3/9/2009

It's 2009, and five years after "Da Band" has broken up, two of its members are (somehow!) still beefing. It started (again?) when E. Ness dissed Chopper City in an interview with WSHH. Chopper responded by releasing a 12-minute video of his own. What he says isn't important; in case you forgot, these are two rappers that you should forget. What Chopper wears, however, is the focus here. It is a Big & Tall-sized gray suit on a Juniors' cheesecake kind-of guy! WSHH commenters let loose with endlessly creative "STEVE HARVEY SUIT" barbs, and life was worth living again.

38. Slim Kid Tre Brings 90210 Actor To The Pharcyde

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37. Asher Roth's Don Imus Twitter Joke

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36. Ice-T Disses Soulja Boy

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Fail Occurred: 6/17/2008

The times we live in: Ice-T, one of the oldest rappers alive, put out a mixtape skit and a YouTube video lecturing Soulja Boy, haranguing him for single-handedly destroying hip-hop. One, who taught Ice-T to use a computer? Two, who allowed him near it? For his part, Soulja Boy put up a hilarious reaction video in which he turned Ice-T's voice off after less than 30 seconds. "Man, fuck all that," he said, before launching into a George Bush-ian missive. "This nigga Ice-T old as fuck!" He and his two cronies mock him for being born in 1958 (ancient!), calling him "the forefather of [Soulja Boy's] nuts." Having been around for so long, Ice-T should know how times change, and just how old he sounds.

35. Girl Tattoos "Drake" On Forehead

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34. Vanilla Ice Flops At The Box Office With Cool As Ice

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33. Shyne Intentionally Changes His Voice

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32. Big Daddy Kane Poses For Playgirl

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31. Main Source Rips Off Large Professor

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30. Lil Kim's $9.99 Mixtape

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29. Sticky Fingaz Gets Beat Up By A White Boy On MTV

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Fail Occurred: 11/5/1998

In what would ultimately resemble bloodsport, Sticky Fingaz (of rap group Onyx) and Californian skateboarder Simon Woodstock squared off in the boxing ring for MTV's Skate & Music Fest. Outweighed by 30 pounds, Sticky ran from Simon like a scene from Godzilla. Jamie Foxx, commentator and Don King impersonator, said, "Ooh, Sticky, you gotta get out of there!" 50 Cent later immortalized the event on "How To Rob," spitting "Tell Sticky gimme the cash before I empty three/I'll beat your ass like that white boy on MTV."

28. Suge Knight Gets Knocked Out (Finally)

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27. Lauryn Hill Flubs MTV Unplugged

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26. Gucci Mane's Ice Cream Cone Face Tattoo

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25. Baby Explains Kissing Lil Wayne On The Mouth

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24. Crooked I Spells His Slaughterhouse Tattoo Wrong

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23. Chris Brown and Drake Instigate Nightclub Bottle Brawl

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22. Eminem's Racist Demo Leaked

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21. Benzino Ruins The Source

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20. Ma$e's Comeback

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19. Ja Rule Tries To Pin An Order Of Protection On 50

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18. Erick Sermon "Falls" Out Of A Window

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17. Sole Bows Down To Company Flow

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16. V-Nasty's Use Of The N-Word

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15. 50 Cent Loses Sales Battle To Kanye West

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14. Professor Griff's Anti-Semitic Rant

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13. Yung Berg's Collective Life Experience

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12. Lil Kim Gets Too Much Plastic Surgery

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11. Game Gets A Butterfly Tattoo On His Face

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10. Jay-Z's Mom Makes Him Apologize For "Super Ugly"

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9. P.M. Dawn's Live Show Gets Bumrushed By BDP

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8. Rick Ross Raps About Date Rape

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7. Gravy's Own Goon Shoots Him In The Ass Outside Hot 97

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6. Charles Hamilton Gets Punched In The Face By A Girl

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Fail Occurred: 5/22/2009

Charles Hamilton had only just begun his fall from grace when he and his manager Briana Latrise were spotted walking down an L.A. street. In the middle of a playful on-camera freestyle battle, Charles insults her, revealing that she'd had an abortion by him. Briana tries to shove his words back into his mouth—literally—with her fist. The bruise may be gone, but he may never recover. Things only got worse when this this GIF hit the Internet.

5. Lil Mama Interrupts Jay-Z & Alicia Keys

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4. LL Cool J Releases "Accidental Racist" With Country Singer Brad Paisley

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Fail Occurred: 4/8/2013
No one's questioning LL Cool J's legacy, especially after comfortably situating himself as one of the best rappers ever. However, his embarrassing inclusion on "Accidental Racist" is a setback that even the Queens MC can't justify. The record starts out innocent enough, with country singer Brad Paisley pandering to his wholesome audience over serene guitar strums. Unbeknownst to the listener, LL bursts in around the four-minute mark with, "Dear Mr. White Man, I wish you understood/What the world is really like when you're living in the hood." Yikes. Topping off the performance with lines like, "If you don't judge my gold chains/I'll forget the iron chains" and "Feel like a new fangled Django, dodging invisible white hoods," makes this a series of hip-hop quotables for all the wrong reasons.

3. Young Buck Cries On The Phone To 50

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Fail Occurred: 6/17/2008

It was like a scene from a gangster movie: Young Buck, on the far end of the phone line, pleading for 50 Cent to let him back onto the G-Unit imprint. He cried. He groveled. He said that he'd never write a diss track against 50 Cent. He...didn't realize that he was being recorded. His career has floundered since. SOMETIMES I JUST GET CONFUSED, FIF!

2. Prodigy Becomes Summer Jam's Tiny Dancer

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1. Rick Ross Becomes Officer Ricky

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