Chris Elliott

Character: Nathanial Mayweather

Ritch Brinkley

Character: Captain Graybar

James Gammon

Character: Paps

Brian Doyle-Murray

Character: Skunk

Brion James

Character: Big Teddy

Melora Walters

Character: Trina

I.M. Hobson

Character: Headmaster Timmons

Alex Nevil

Character: Thomas

David H. Sterry

Character: Lance

Bob Elliott

Character: William Mayweather

Edward Flotard

Character: Limo Driver

Jim Cummings

Character: Cupcake (voice)

David Letterman

Character: Old Salt In Fishing Village

Ann Magnuson

Character: Calli

Russ Tamblyn

Character: Chocki

Ricki Lake

Character: Figurehead

Mike Starr

Character: Mulligan

Andy Richter

Character: Kenny

Alfred Molina

Character: School Professor (uncredited)

Ralph Moratz

Character: Finishing School Groundskeeper (uncredited)

Adam Reeves

Character: Doorman (uncredited)

Tommy Williamson

Character: Face in the Clouds (uncredited)