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)