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In 2002, he played the role of Amos Hart, Roxie Hart's naïve husband, in the musical film Chicago.In 2006, he performed two songs on Rogue's Gallery: Pirate Ballads, Sea Songs, and Chanteys: "Fathom the Bowl" and "My Son John".In 2007, Reilly starred in the biopic parody Walk Hard: The Dewey Cox Story.
Reilly frequently appeared on the sketch comedy program Tim and Eric Awesome Show, Great Job! In early 2011, Reilly collaborated with director Miguel Arteta for a second time with the comedy Cedar Rapids, starring Ed Helms.He voiced the title character in the commercially successful animated film Wreck-It Ralph (2012), and appeared in the superhero film Guardians of the Galaxy (2014), as well as Kong: Skull Island (2017).Since 2010, Reilly has been starring in the television series Check It Out! Steve Brule, playing the titular character that originated on Tim and Eric Awesome Show, Great Job! Reilly performs with his band John Reilly and Friends and worked as a stage actor in True West (2000), for which he was nominated for the Tony Award for Best Actor in a Play.is an American actor, comedian, singer, screenwriter, and producer.He made his film debut in Brian De Palma's war film Casualties of War (1989).
Reilly appeared in Martin Scorsese's 2004 Howard Hughes biopic, The Aviator, as Noah Dietrich, Howard Hughes' (Leonardo Di Caprio) trusted business partner.