Peņa was born and raised in Chicago, to an immigrant family originally from Mexico. After graduating from high school, he went to an open casting call for the Peter Bogdanovich feature To Sir, with Love II (1996) (TV), and to his surprise, beat out hundreds of other young men for a role. After relocating to Los Angeles Peņa quickly booked a succession of roles in features including Star Maps, My Fellow Americans (1996) (opposite Jack Lemmon and James Garner), La Cucaracha (1998) (winner of the Best Picture in the Austin Film Festival), Bellyfruit (1999), and the Disney/Jerry Bruckheimer feature Gone in Sixty Seconds (2000).