Nathanial Mayweather

Chris Elliott

Captain Greybar

Ritch Brinkley

Calli

Ann Magnuson

Paps

James Gammon

Skunk

Brian Doyle-Murray

Big Teddy

Brion James

Trina

Melora Walters

Chocki

Russ Tamblyn

Kenny

Andy Richter

Figurehead

Ricki Lake

Headmaster Timmons

I.M. Hobson

Thomas

Alex Nevil

Old Salt In Fishing Village

David Letterman

Mulligan

Mike Starr

Lance

David H. Sterry

William Mayweather

Bob Elliott

Limo Driver

Edward Flotard

School Professor (uncredited)

Alfred Molina

Cupcake (voice)

Jim Cummings

Lance

David Sterry

Sharon Bialy

Debi Manwiller

Finishing School Groundskeeper (uncredited)

Ralph Moratz

Doorman (uncredited)

Adam Reeves

Richard Pagano