In 1996, Osborne played the father of Tom Everett Scott's character in the musical comedy-drama movie "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".