Chris Elliott
Nathanial Mayweather
Ritch Brinkley
Captain Graybar
James Gammon
Paps
Brian Doyle-Murray
Skunk
Brion James
Big Teddy
Melora Walters
Trina
I.M. Hobson
Headmaster Timmons
Alex Nevil
Thomas
David H. Sterry
Lance
Bob Elliott
William Mayweather
Edward Flotard
Limo Driver
Jim Cummings
Cupcake (voice)
David Letterman
Old Salt In Fishing Village
Ann Magnuson
Calli
Russ Tamblyn
Chocki
Ricki Lake
Figurehead
Mike Starr
Mulligan
Andy Richter
Kenny
Alfred Molina
School Professor (uncredited)
Ralph Moratz
Finishing School Groundskeeper (uncredited)
Adam Reeves
Doorman (uncredited)
Tommy Williamson
Face in the Clouds (uncredited)