I try to take things that challenge me either physically or mentally, or I have to learn a new skill.

Reilly performed on two tracks of the 2006 compilation Rogue's Gallery: Pirate Ballads Sea Songs and Chanteys: “Fathom the Bowl” and “My Son John”. In 2007 Reilly starred as the title character in parody bio-pic Walk Hard: The Dewey Cox Story singing various songs parodying Johnny Cash Ray Charles and others. Although the role of Hatcher was written as a small one De Palma liked Reilly's performance so much that the role was significantly expanded.

To date he has appeared in more than fifty films including three separate films in 2002 that were all nominated for the Academy Award for Best Picture. Steve Brule a television show on Adult Swim since its premiere on May 16 2010. He has been nominated for an Academy Award for Best Supporting Actor for his role in Chicago and a Grammy Award for the song "Walk Hard" which he performed in Walk Hard: The Dewey Cox Story.