Our 5 Favorite Worst Hip-Hop Fails Of All Time

Becky Bain | June 17, 2010 4:12 pm

Complex released a comprehensive list of the 50 Worst Hip-Hop Fails of All Time, and it’s filled with comedy gold—actors trying to rap, rappers trying to act, lame beefs, humiliating performances and a ton of “oops!” moments from hip-hop artists that they probably hoped people would have forgotten by now. No such luck! Our 5 favorites below:

#30 Vanilla Ice tries to be an actor.

What Complex Says: “Despite having the same cinematographer as Schindler’s List, Vanilla Ice’s star-killing vehicle Cool As Ice did not win any Oscars. In fact, it might be the worst movie ever, a bitter end to Rob Van Winkle’s 12-month career death knell.” What We Say: Makes a great drinking game! Every time you suffer second hand embarrassment for everyone involved in this movie, take a drink. (Warning: you may die of alcohol poisoning before the main credits are over.)

#39 Brian Austin Green tries to be a rapper.

What Complex Says: “As David Silver on the original Beverly Hills 90210, Brian Austin Green tried his hand at rapping and DJing. Remember: that was a TV show. Fake. Well, in 1996, the grown-up Brian Green (no Austin) decided that it wasn’t just his character’s passion—it was his own. With The Pharcyde’s Slim Kid 3 making the beats, Brian Green dropped his album One Stop Carnival…with a thud.” What We Say: Thanks, Brian, for paving the way for The Situation’s rap single to exist.

#18 Lil Mama pulls a Kanye West on Jay-Z and Alicia Keys moments after “pulling a Kanye” becomes a thing.

What Complex Says: “[Lil Mama] wandered the stage like a kid sister or stray mutt, ignored and forgotten, before striking a b-girl pose. (Her apology said that her “emotions were running high.” Sad.) It would probably have been a bigger moment in pop-culture history if more people knew who she was.” What We Say: This is so much funnier than Kanye’s Taylor Swift interruption, because at least Kanye had a statement to make. We wish this had been parodied more in pop culture, but alas, Complex is right—most people don’t know who Lil Mama is. And, surprisingly, this moment didn’t help her get much publicity.

#49 Game gets dumped on dating TV show.

What Complex Says: “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.” What We Say: At least he didn’t star in Degrassi.

#8 Game (yes! another Game one) gets a tramp stamp on his face.

What Complex Says: “In May 2005, Game had a butterfly—wings spread—tattooed beneath his right eye, a signifier of ‘new life’… everything was fine until people made fun of him because, you know, he’s a rapper and rappers aren’t supposed to have butterfly tattoos on their faces. So, he got the Dodgers’ LA logo drawn over it.” What We Say: We have nothing to say—we’re too busy giggling over this photo.

Check out the rest of Hip-Hop’s biggest blunders over at Complex.