Donald Petrie Director Macaulay Culkin Richard "Richie" Rich Jr. Actor John Larroquette Lawrence Van Dough Actor Edward Herrmann Richard Rich Sr. Actor Jonathan Hyde Herbert Arthur Runcible Cadbury Actor Christine Ebersole Regina Rich Actor Stephi Lineburg Gloria Actor Michael McShane Professor Keenbean Actor Chelcie Ross Mr. Ferguson Actor Mariangela Pino Diane Pazinski Actor Michael Maccarone Tony Actor Joel Robinson Omar Actor Jonathan Hilario Pee Wee Actor Reggie Jackson Mr. Jackson, the baseball coach Actor Claudia Schiffer Aerobics Instructor Actor Wandachristine Newswoman at Factory Actor Stacy Logan Nash Actor Eddie Bo Smith Jr. Ambler Actor Kent Logsdon Zullo Actor Bob Riley President Actor David Fawcett Chauffeur Actor Dawn Maxey Ms. Fairchild Actor Ben Stein School Teacher Actor Sean A. Tate Reynolds Actor Joel Ellegant Ellsworth Actor Justin Zaremby Reginald Actor John Drury Newscaster Actor Diann Burns Newscaster Actor Rush Pearson Prison Lowlife Actor Rachel Stephens Richie's Secretary Actor Nydia Rodriguez Terracina Richie's Secretary Actor Neil Tolkin Writer Tom S. Parker Writer Jim Jennewein Writer John Davis Producer Joel Silver Producer Joe Bilella Executive Producer Dan Kolsrud Executive Producer Jon Shapiro Executive Producer Don Burgess Cinematographer Malcolm Campbell Film Editing Alan Silvestri Original Music James Spencer Production Design Bill Matthews Art Director John Anderson Set Decoration Patricia Malone Set Decoration Lisa Jensen Costume Design Margery Simkin Casting