Paul Reubens
Pee-wee Herman
Penelope Ann Miller
Winnie
Kris Kristofferson
Mace Montana
Valeria Golino
Gina Piccolapupula
Benicio del Toro
Duke the Dog-Faced Boy
Wayne White
Vance the Pig (voice)
Susan Tyrrell
Midge Montana
Albert Henderson
Mr. Ryan
Jack Murdock
Otis
David Byrd
Deke
Mary Jackson
Mrs. Dill
Frances Bay
Mrs. Haynes
Leo Gordon
Joe the Blacksmith (as Leo V. Gordon)
Anne Seymour
Pearl
Kenneth Tobey
Sheriff
Stephanie Hodge
Mermaid
Franco Columbu
Otto the Strongman
Kevin Peter Hall
Big John
Lynne Marie Stewart
Zelda the Bearded Lady
Dustin Diamond
Child - Deke
Jay Robinson
Cook
Kevin B. Kaplowitz
Child - Mr. Ryan
Jeffrey R. Shaw
Child - Otis
Marie Hawkins
Child - Pearl
Shea Joachim
Child - Sheriff
Molly Ann Carter
School Child
Myka Peck
School Child
Patricia M. Peters
Web Girl
Joey Arias
Shim
Matthias Hues
Oscar - Lion Tamer
Vance Colvig
Clownie
April Tatro
Human Pretzel