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)