Accepted to New York University, but chose to pursue an acting career instead of attending

First acting role was an episode of the FOX series, "Party of Five"

Modeled for a Tommy Jeans ad campaign

Featured as part of an ensemble cast in the 1980s period comedy "200 Cigarettes"

Appeared in the psychological thriller "Gossip"

Breakthrough role as Penny Lane in Cameron Crowe's "Almost Famous"; earned a Supporting Actress Academy Award nomination

Played Richard Gere's spoiled daughter in Robert Altman's "Dr. T and the Women"

Played the female lead, opposite Heath Ledger, in the remake of "Four Feathers"

Co-starred with Matthew McConaughey in the romantic comedy "How to Lose a Guy in 10 Days"

Played five different characters in the romantic comedy "Alex and Emma"

Co-starred with John Corbett as a woman raising her sister's three children in Gary Marshall's "Raising Helen"

Headlined the thriller, "The Skeleton Key," co-starring Gena Rowlands and John Hurt

Co-starred with Matt Dillon as newlyweds in the comedy "You, Me and Dupree"

Directed first short, "Cutlass," one of Glamour magazine's 'Reel Moments'; co-starred Kurt Russell and Dakota Fanning

Re-teamed with Matthew McConaughey for "Fool's Gold"