7. LL Cool J in Toys
We’ve got nothing but love for the self-proclaimed G.O.A.T. (greatest of all time), but Ladies Love Cool James has a few questionable acting moments on his film resume that cannot be ignored. Rollerball and Deep Blue Sea are more than qualified to make this list, but LL’s weird role as Captain Patrick Zevo in the zany 1992 movie Toys will totally suffice as the frontrunner in this case. This was ’92, y’all. LL was just coming off of Mama Said Knock You Out. This wasn’t a huge role for LL in this goofy flop, but it was most definitely enough to make his fans scratch their heads in disbelief. Stick to Walking with a Panther, LL.
6. Method Man and Redman in How High
I’m well aware that this seems like a no-brainer for these two iconic stoners, but Method Man and Redman’s shameful cookie cutter roles in How High could quite possibly be the exact moment where the pair jumped the shark from legit artists that should be taken seriously to two cartoon characters just trying to make a quick dollar bill.
Based on my love for Half Baked, I had really *cough* high expectations for this movie, but if you’re a true fan of hip-hop, there’s no doubt that How High made you cringe from start to finish. Method Man and Redman are easily two of the greatest MCs ever to rock the mic, but some of the lines delivered by the goofy duo throughout How High could make any die-hard stick his head into muddy waters.
5. Queen Latifah in Bringing Down the House
For those of you that remember Queen Latifah from her old school rapping days, you know that she took her work very seriously. From her start in Ladies Fresh to puttin’ down feminist rap gems like "Ladies First" and "U.N.I.T.Y.," Queen Latifah was a proud black women who did not mince words. Unfortunately, times have changed.
After receiving critical acclaim for her work in Chicago, Ms. Latifah seemed to change her tune and began to take part in some extremely suspect Hollywood projects. There are a few facepalms to choose from here, but her transformation into Charlene Morton for Bringing Down the House is easily the most shameful of the lot. I just have no idea how a woman with Latifah’s backround would play a character so stereotypical and cartoony as she in this film. Just keep in mind that this role was played by the same chick who had an album entitled Nature of a Sista.
4. Ludacris in Fred Claus
How things like this actually happen is beyond me.
Ludacris’ role as Skinny Black in Hustle & Flow is easily the best and most natural work he’s ever done on the big screen. His portrayal as Ludacrismas in the mind-boggling Christmas comedy Fred Claus is a whole different story. Luda doesn’t grace the screen too many times as the pint-sized North Pole disc jockey, but the few moments that he’s CG’d on the body of midget, all hell seriously breaks loose. For those of you that haven’t had the pleasure, Ludacrismas gets into a rumble with Vince Vaughn. Yes, Vince Vaughn.
3. Vanilla Ice in Cool as Ice
Where to start? First and foremost, it needs to be said that not only did Vanilla Ice have a respectable following in legit hip-hop/rap circles early in his career, the dude also actually had some solid skills on the dance floor as well as on the mic. It’s true that Rob Van Winkle sold the genre out to the pop world just make a few bucks, but he wasn’t the only one. Acts like MC Hammer were producing the same type of material and didn’t quite seem to get the same level of hate from audiences like Vanilla did. People just really had it out for the guy.
With this said, his role as Johnny in the 1991 motorcycle wreck Cool as Ice was the straw that broke the camel’s back and gave everyone the ultimate ammo for ripping Ice a new one. His work in this film seriously deserves a Lifetime Achievement Razzie award. It’s honestly that bad.
2. Ice Cube in Are We There Yet?
For a guy that made a name for himself helping pen gangsta rap classics like "F*** tha Police" and "Straight Outta Compton," it was pretty insane to see Ice Cube in a cheesy family film acting super wacky while getting terrorized by two little kids. I’m not hating on Cube here. We’re all aware that fools need to pay the bills, but talk about a persona 180. There’s a classic Internet photo of a vintage Cube holding an AK-47 photoshopped next to a pic of him from Are We There Yet wearing a goofy-ass life vest. I think that it best explains the ridiculousness of Ice Cube’s starring role in this movie.
1. Ice-T in Law & Order: Special Victims Unit
Ice-T has played cops in the past in such cult classics as New Jack City, but due to his notorious 1992 anti-police anthem "Cop Killer," you would think Tracy Morrow would do pretty much everything and anything in his power to not portray a copper on screen. That’s why his longstanding role on Law & Order: Special Victims Unit is seriously one of the most perplexing career moves in the history of the entertainment industry. Dressing up as a cop on the cover of Rolling Stone is one thing, but playing a cheesy cookie-cutter version of one on a show like SVU is a completely different can of worms. There are other ways to get a paycheck, T.