Chris Elliott as Nathanial Mayweather

Ritch Brinkley as Captain Graybar

James Gammon as Paps

Brian Doyle-Murray as Skunk

Brion James as Big Teddy

Melora Walters as Trina

I.M. Hobson as Headmaster Timmons

Alex Nevil as Thomas

David H. Sterry as Lance

Bob Elliott as William Mayweather

Edward Flotard as Limo Driver

Jim Cummings as Cupcake (voice)

David Letterman as Old Salt In Fishing Village

Ann Magnuson as Calli

Russ Tamblyn as Chocki

Ricki Lake as Figurehead

Mike Starr as Mulligan

Andy Richter as Kenny

Alfred Molina as School Professor (uncredited)

Ralph Moratz as Finishing School Groundskeeper (uncredited)

Adam Reeves as Doorman (uncredited)

Tommy Williamson as Face in the Clouds (uncredited)