Cabin Boy

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