Charlie Sheen Topper Harley / Rhett Butler / Superman Cary Elwes Kent Gregory Valeria Golino Ramada Thompson / Scarlett O'Hara / Lois Lane Lloyd Bridges Admiral Benson Kevin Dunn Lt. Commander Block Jon Cryer Jim 'Wash Out' Pfaffenbach William O'Leary Pete 'Dead Meat' Thompson Kristy Swanson Kowalski Efrem Zimbalist Jr. Wilson Bill Irwin Buzz Harley Heidi Swedberg Mrs. 'Dead Meat' Thompson Bruce A. Young 'Red' Herring Ryan Stiles 'Mailman' Farnham Ryan Cutrona Captain Margolis Don Lake Doctor Kelly Connell Air Controller Tony Simotes Ambulance Driver Don Luce Paramedic Jimmy Lennon Jr. Ring Announcer Marie Thomas-Foster Francine Pat Proft Lawrence Lipps Marc Shaiman Piano Player Cylk Cozart Drill Sergeant #1 Jimmie Ray Weeks Amish Man Annie O'Donnell Amish Woman Charles Barkley Charles Barkley Bill Laimbeer Bill Laimbeer Eugene Greytak Pope John Paul II Tony Lorea Humphrey 'Bogie' Bogart Jerry Haleva Saddam Hussein Elston Ridgle Boxer #1