Brad Pitt Billy Beane Jonah Hill Peter Brand Philip Seymour Hoffman Art Howe Robin Wright Sharon Chris Pratt Scott Hatteberg Stephen Bishop David Justice Reed Diamond Mark Shapiro Brent Jennings Ron Washington Ken Medlock Grady Fuson Tammy Blanchard Elizabeth Hatteberg Jack McGee John Poloni Vyto Ruginis Pittaro Nick Searcy Matt Keough Glenn Morshower Ron Hopkins Casey Bond Chad Bradford Kerris Dorsey Casey Beane Arliss Howard John Henry Reed Thompson Young Billy James Shanklin Billy's Dad Diane Behrens Billy's Mom Takayo Fischer Suzanne - Billy's Secretary Derrin Ebert Mike Magnante Gerardo Celasco Carlos Peña Ken Rudulph Reporter Lisa Guerrero Reporter Joe Satriani Self Simon James Voos Eddie Frierson Call-In Radio Host (voice) Eric Winzenried PR Guy Derek Jeter Himself (archive footage)