O'Donnell was discovered when he was cast in a McDonald's commercial, in which he served Michael Jordan.
At the age of seventeen, he was offered a chance to audition for a part in the movie Men Don't Leave, with Jessica Lange, and he won the role.
In the early 1990s, O'Donnell was a featured player in many successful movies such as Fried Green Tomatoes (1991) and Scent of a Woman (1992).
With the success of Circle of Friends (1995), O'Donnell further cemented his place in Hollywood's A-list when he was chosen over Leonardo DiCaprio for the role of Robin in the hugely successful Batman Forever. The role of Robin was one of the most sought-after roles at that time. O'Donnell was part of a field that included Leonardo DiCaprio, Matt Damon, Christian Bale (who went on to play the Dark Knight himself in "Batman Begins"), Corey Haim, Corey Feldman, Tobey Stephens, and Scott Speedman. Producers narrowed their choices to DiCaprio and O'Donnell. At a comic book convention, they asked the young boys attending which actor could beat the other in a fistfight. When the boys overwhelmingly declared O'Donnell the winner, he was ultimately given the role.
O'Donnell followed that film with an appearance in the 1996 film The Chamber, based on the John Grisham novel. He subsequently appeared in the "Batman" sequel, Batman & Robin, in 1997. Critically panned, the movie turned out to be one of the largest box office failures in history.
O'Donnell did not appear in another movie for two years. His next appearance was in the Robert Altman film Cookie's Fortune, as part of the ensemble. His more mainstream comeback films The Bachelor (1999) and Vertical Limit (2000) were only moderately successful.
Following Vertical Limit, a four-year hiatus led many to believe he had met the same career fate of his Batman & Robin co-star Alicia Silverstone. However, in 2004, he appeared in the widely praised Kinsey.
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