In 1996, Osborne played the father of Tom Everett Scott's character in the musical comedy-drama film That Thing You Do!. In 1999, he guest starred, along with Lance Henriksen (reprising his role as Frank Black), in an episode of The X-Files as a necromancer for the Millennium Group. In 2000, he starred as Kirsten Dunst's father in the teen comedy Bring It On.
Osborne then starred as Eddie Darko, the main character's father, in the science fiction drama film Donnie Darko (2001). He then appeared in the family comedy Cheaper by the Dozen (2003). The following year, he co-starred in the comedy film Anchorman: The Legend of Ron Burgundy. In 2006, Osborne starred as the main villain in the Disney film Air Buddies. In 2007, he reunited with Donnie Darko Director Richard Kelly on the dramedy thriller film Southland Tales, and again in 2009 on the psychological thriller film The Box. Also in 2009, he co-starred in the comedy film All About Steve.
In 2011, he has a supporting role in the Tom Hanks film Larry Crowne. He has made appearances on television series such as House M. D., Cold Case, CSI: Miami, Rules of Engagement, Dharma & Greg, and had a recurring role on the ABC science fiction series Invasion.
