Osborne then starred as Eddie Darko, the main character's father, in the science fiction drama movie "Donnie Darko" (2001). He then appeared in the family comedy "Cheaper by the Dozen" (2003). The following year, he co-starred in the comedy movie "". In 2006, Osborne starred as the main villain in the Disney movie "Air Buddies". In 2007, he reunited with "Donnie Darko" director Richard Kelly on the dramedy thriller movie "Southland Tales", and again in 2009 on the psychological thriller movie "The Box". Also in 2009, he co-starred in the comedy movie "All About Steve".