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In 2000, during the fourth season of 7th Heaven, Biel commented that she grew tired of playing the wholesome preacher's kid, and blamed the show for giving her a squeaky-clean image, which caused her to lose out on a role in American Beauty (the part went to Thora Birch). In a last ditch attempt to be let out of her contract, she posed semi-nude for the cover of Gear magazine. Fans and producers of 7th Heaven were outraged, and the shoot also sparked a lot of controversy, as Biel was still a minor at the time, but Aaron Spelling made it clear that Biel would be staying with the show until her contract was due to expire (although, she appeared in minimal episodes in season five, due to her attending college out of state). photos of jessica biel She has now claimed that she regrets the Gear shoot, but considers it a learning experience.

In 2001, Biel played the love interest of Freddie Prinze, Jr. in the baseball themed movie, Summer Catch. The next year, she starred as promiscuous college student Lara in the ensemble, The Rules of Attraction, a film adaptation of the Bret Easton Ellis novel of the same name.

In Next, Biel played alongside Nicolas Cage and Julianne Moore. She then played in the summer comedy, I Now Pronounce You Chuck and Larry, co-starring Adam Sandler and Kevin James. Like her earlier film, The Texas Chainsaw Massacre, Chuck and Larry received mixed pussy reviews, but opened its first week at number one at the box office. She also produced and starred in a short film titled Hole in the Paper Sky, which was released in 2008.