Navigating a career in Hollywood is tricky business. You can be a part of several massive hits, but one bad decision can put a pox upon your name. And imagine the whiplash of landing the lead role in a much-hyped movie, only to win a shelf full of Razzies for your efforts.

Here are a few such ill-fated actors, and the cursed roles that derailed their careers:

Lindsay Lohan AUBREY FLEMING DAKOTA MOSS CRACKEDCON Lohan was a fixture in Hollywood for most of her life, but she seemed to hit her expiration date w

Orlando Bloom DREW BAYLOR After Bloom found massive success in high fantasy and pirate movies, the 2005 drama Elizabethtown did the impossible: it mad

Tom Green GORD BRODY Green started his career as an improbable rapper, then became an improbable television host, but it all came crashing down after

Pamela Anderson BARB WIRE CRACKED COM Only one thing could stop her meteoric rise to stardom: an awful comic book adaptation. Anderson blames the stud

Join the Cracked Movie Club

Expand your movie and TV brain--get the weekly Cracked Movie Club newsletter!

Halle Berry CATWOMAN CRACKED.CO After the debacle that was 2004's Catwoman, there were calls for her to return her Oscar. She has managed to hold onto

Chris Klein JONATHAN CROSS CRACKED COR Klein was strapped into a dorky helmet and plopped next to LL Cool J in the absolute bomb Rollerball (2002). It

Demi Moore ERIN GRANT Moore was unstoppable through the mid-9o's, but she was too closely tied to the 1996 flop Striptease. Disney even started freaki

Mike Meyers GURU PITKA CRACKEDcO COM Meyers has made some massive hits, but even more extremely questionable duds. 2008's The Love Guru seems to have

Topher Grace VENOM CRACKEDCON Grace left That 70's Show to pursue a film career, and was gaining some momentum. 2007's Spider-Man 3 was supposed to be

Adam Sandler JACK/ JILL CRACKEDCON He did just make a critical comeback in the more serious Uncut Gems, but 2011's Jack and Jill was probably the last

Elizabeth Berkley NOMI MALONE Fresh off of a wildly successful run on Saved By The Bell, Berkley took a gamble on the risky, semi-raunchy, NC-17 rated

Cuba Gooding, Jr. JERRY ROBINSON CRACKED COM For a while there, Cuba couldn't make a bad movie if he tried - until 2002's Boat Trip. Who would've thou

Jennifer Lopez RICKI 2003's Gigli has ruined more than its fair share of careers. Jennifer and Ben Affleck made it out alive, but Lopez' career never

Josh Hartnett SLEVIN KELEVRA CRACKED COM Hartnett was more or less blamed for the failure of 2006's star-studded Lucky Number Slevin. The movie marked

Alicia Silverstone BATGIRL She cashed in her Clueless cred on the now-infamous Batman & Robin, garnering a Razzie and not much else. She's had a lot o

Justin Chatwin GOKU Landing the role of Goku should have launched Chatwin to stardom, but Fox fumbled 2009's Dragonball EvOlUtion SO badly that we hav

Freddie Prinze Jr. FRED JONES CRACKED COM As he started to age out of teen heartthrob territory, he had a hard time finding his niche. He spent the la

Meg Ryan ALICE BOWMAN Meg Ryan and costar Russell Crowe began dating while filming 2002's Proof of Life. Their controversial relationship sucked up al

Sean Connery ALLAN QUATERMAIN CRACKED COM 2003's The League of Extraordinary Gentlemen was such a critical and popular disappointment that Connery ret

John Travolta TERL CRACKED COM After a Tarantino-fuelled resurgence in Pulp Fiction, Travolta went down a dark road starting with the 2000 L. Ron Hubb

Forgot Password?