He starred in over 80 films such as Hard Eight (1996), Boogie Nights (1997), Magnolia (1999), Gangs of New York (2002), Step Brothers (2008) and was nominated for an Academy Award and Golden Globe for Best Supporting Actor for the role of Amos Hart, in the celebrated musical Chicago (2002). In 2007 he was nominated at the Grammys and again at the Golden Globes for the song Walk Hard that he performed in Walk Hard: The Dewey Cox Story. He also starred in the „Check It Out! with Dr. Steve Brule” TV show playing a character based on the series of comic sketches created by Tim Heidecker and Eric Wareheim for Adult Swim.