O'Leary next appeared in another thriller, Frailty, directed by Bill Paxton, and in the kids comedy Spy Kids 2: The Island of Lost Dreams, both of which opened in 2002 to positive reviews, gaining O'Leary recognition among teenage audiences. In 2003, O'Leary had a minor role in the third Spy Kids film, Spy Kids 3-D: Game Over, and also appeared in the 2004 drama The Alamo, although most of his role was reduced to one line.