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For his performance in Chicago (2002), Reilly was nominated for the Academy Award for Best Supporting Actor and the corresponding Golden Globe Award.He worked with director Martin Scorsese on both Gangs of New York (2002) and The Aviator (2004).
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.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".Reilly gained exposure through his supporting roles in Days of Thunder (1990), What's Eating Gilbert Grape (1993), and The River Wild (1994).He also starred in Paul Thomas Anderson's films, Hard Eight (1996), Boogie Nights (1997) and Magnolia (1999).
The second single features Ray Price's "I'll Be There If You Ever Want" as well as the country classic "I'm Making Plans", performed with Becky Stark.