Stardom is like any great game of strategy -- it's both a combination of blind luck and a series of carefully calculated decisions. This decade produced several regrettable ones -- here's ten of the worst.
10. Cuba Gooding Jr. as Jerry Robinson in Boat Trip (2002)
Having coasted into the new century on the gilded wings of an Oscarcorn, it seemed nothing could stop the irrespressible Jerry Maguire breakout with the currency-related catchphrase. Then, uh, Boat Trip happened, and a link between actor, terrible movies, and the gay cruise circuit was forged for all eternity. That he chose to follow it up by going F.R. in Radio didn't help matters.
9. Chris Klein as Jonathan Cross in Rollerball (2002)
The American Pie golden boy only upped his cred with his turn as Election's endowed jocktard, but the next logical step -- action hero on wheels -- turned into a multi-vehicle collision with one of the decade's most infamous bombs. How bad was it? So bad, in fact, it brought a federal indictment for its director.
8. The Entire Cast of Scooby-Doo in Scooby Doo (2002)
Freddie, Freddie-Doo, where are you? You're somewhere voicing Delgo! Sarah Gellar who? Lillard, too! This didn't very well go.
7. Haley Joel Osment as Walter in Secondhand Lions (2003)
Did anyone ever see this movie? Something about jungle cats and gay uncles? Apparently it wasn't terrible, and yet it definitely marked a turning point in Osment's trajectory. 'Twas puberty, killed the heat.
6. Rupert Everett as Robert Whittaker in The Next Best Thing (2000)
Rupert Everett will be the first to tell you that coming out of the closet will kill an actor's career. What he might not mention, however, is that doing it in the precise way he chose to do it -- by playing bosom knock-upper to upwardly mobile yogacist Madonna -- brings the most swift, but painful, sleep.
5. Thora Birch as Empress Savina in Dungeons & Dragons (2000)
"Hey Thora! You just starred in the most breathlessly praised, zeitgeisty movie about suburban ennui of the decade! What are you going to do next?!" "I'm going to Troll-Infested Virginland!"
4. Meg Ryan as Frannie in In the Cut (2003)
The '90s were Meg's. She managed to hold on until 2001, with the time-travel romcom Kate & Leopold, but by the time Jane Campion's ill-conceived psychoRuffalosexual thriller rolled around, things started to slide. (And I'm not just talking about her face.) (Though I'm partially talking about her face.)
3. Mike Meyers as Maurice / Guru Pitka / Young Pitka / Teenage Pitka / Himself in The Love Guru (2008)
Namasterrible.
2. Lindsay Lohan as Aubrey Fleming / Dakota Moss in I Know Who Killed Me (2007)
This could have also gone to Georgia Rule, but I Know Who Killed Me is still really the seminal moment when Lohan's career finally stopped resisting the magnetized stripper pole that had been pulling at her for years, sending the wayward shock-starlet hurtling through the air and into it with a loud, reverberative, "CLANGGGNNGNGNGNG..."
1. Eddie Murphy as Norbit / Rasputia / Mr. Wong in Norbit (2007)
It was to be his Moment™ -- the culmination of the unprecedented career of a comedy giant whose greatest performances were long behind him, but who still had one legendary role inside him just ready to explode from every pore. Then a 400-pound stereotype named Rasputia slowly lowered her ample girth over the statuette that was to be his, each golden centimenter slowly disappearing until, finally, its base vanished completely and forever. R.I.P. Eddie's Oscar.