Barris decides not to correct Penny. Cast Sam Rockwell as Chuck Barris Michael Cera as Young Chuck Barris Drew Barrymore as Penny Pacino George Clooney as Jim Byrd Julia Roberts as Patricia Watson Rutger Hauer as Keeler Jerry Weintraub as Larry Goldberg Robert John Burke as Instructor Jenks Michael Ensign as Simon Oliver Maggie Gyllenhaal as Debbie James Urbaniak as Rod Flexner Rachelle Lefevre as Tuvia Kristen Wilson as Loretta Daniel Zacapa as Renda Emilio Rivera as Benitez Carlos Carrasco as Brazioni Richard Kind as Casting Executive Brad Pitt as Bachelor #1 Matt Damon as Bachelor #2 Jen Taylor And Spencer Kayden as Crowd Scenes (uncredited) Barris, Dick Clark, Jim Lange, Murray Langston, Jaye P. Morgan, and Gene Patton are featured in interviews central to the storyline. Production Development Chuck Barris first sold the film rights of his "unauthorized autobiography" to Columbia Pictures in the late 1980s. Columbia president Dawn Steel greenlighted Confessions of a Dangerous Mind with Jim McBride directing. McBride offered the lead role to Richard Dreyfuss, who refused to read the script because he believed Barris's morbid humor was distasteful. The project was abandoned at Columbia when Steel was fired in 1989. Producer Andrew Lazar optioned the film rights from Columbia in 1997 and set Confessions of a Dangerous Mind at Warner Bros. Pictures that same year. Charlie Kaufman entered discussions to write a new screenplay in June 1997 and finished his first draft later that year. Barris gave positive feedback to Kaufman's script and Curtis Hanson instantly agreed to direct with Sean Penn in the lead role and George Clooney and Drew Barrymore attached to co-star. Hanson eventually dropped out, but with the financial success of My Best Friend's Wedding (1997), P. J. Hogan entered discussions with Warner Bros. to direct in January 1998. Mike Myers signed on to replace Sean Penn, who vacated the lead role. However, negotiations with Hogan fell through; Sam Mendes, David Fincher and Darren Aronofsky all became interested in taking over the director's position. Fincher and Myers were fast tracking production for Confessions of a Dangerous Mind in April 2000 but Fincher dropped out and, by that October, Brian De Palma was attached to direct with Renaissance Pictures co-financing. Later that month, Warner Bros. put the project in turnaround, and Myers lost interest. Russell Crowe, Kevin Spacey, and Edward Norton had also been attached to the film in the early development