Film Career
Reilly made his film debut in the Brian De Palma film Casualties of War (1989) as P.F.C. Herbert Hatcher. 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. Also notable in his film work throughout the 1990s was his supporting role alongside Mark Wahlberg in Paul Thomas Anderson's 1997 film Boogie Nights, in which he played the pornographic film star Reed Rothchild. Reilly was a frequent collaborator of Anderson's in the 1990s, including other roles in Hard Eight, Magnolia and a cameo in the video for the Fiona Apple single Across the Universe, which Anderson directed.
He appeared in Days of Thunder (1990) as stock car crew member “Buck Bretherton” – in 2006 he revisited this film’s subject matter as the character of race car driver “Cal Naughton, Jr.” in Talladega Nights: The Ballad of Ricky Bobby.
In 2002 he appeared in three of the year's Academy Award for Best Picture nominees – Chicago, Gangs of New York and The Hours. The three movies were nominated for a total of thirty-two Oscars, including one for Best Supporting Actor for Reilly's performance as Renée Zellweger's trusting husband in Chicago. Ultimately, Chicago won six, The Hours won one, and Gangs of New York won none.
Reilly appeared in Martin Scorsese's 2004 Howard Hughes biopic, The Aviator, as Hughes' (played by Leonardo DiCaprio) trusted business partner, Noah Dietrich. Of the role Reilly said, “Noah was almost a father figure to Hughes... Howard would have a scheme, and it was Noah who had to say, ‘We don’t have the money.’ He was one of his few friends.” He reportedly quit the 2005 film Manderlay to protest the on-set killing of a donkey. He appeared in Adam McKay's Talladega Nights: The Ballad of Ricky Bobby in 2006, as Cal Naughton, Jr., the title character's best friend, alongside Will Ferrell. He also starred alongside Woody Harrelson, Meryl Streep, and Lindsay Lohan among others in the Robert Altman film A Prairie Home Companion. 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. The next year, Reilly reunited with Ferrell to star in Step Brothers.
In 2008, he was among the many notable actors to perform in the online political musical, Proposition 8 - The Musical.
Then in 2009, he played the role of Larten Crepsley from the motion picture Cirque du Freak: The Vampire's Assistant and provided the voice of "5" in 9. Reilly also appeared in the 2010 film Cyrus.
Reilly has stated that he would be very determined to play the lead role of Nathan Detroit if a revival of the musical Guys and Dolls were to occur.
In March 2012, he was featured in a performance of Dustin Lance Black's play, '8' — a staged reenactment of the federal trial that overturned California's Prop 8 ban on same-sex marriage — as David Blankenhorn. The production was held at the Wilshire Ebell Theatre and broadcast on YouTube to raise money for the American Foundation for Equal Rights, a non-profit organization funding the plaintiffs' legal team and sponsoring the play.
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