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
Leo Gordon
Joe the Blacksmith (as Leo V. Gordon)
Franco Columbu
Otto the Strongman
Lynne Marie Stewart
Zelda the Bearded Lady
Dustin Diamond
Child - Deke
Kevin B. Kaplowitz
Child - Mr. Ryan
Jeffrey R. Shaw
Child - Otis
Marie Hawkins
Child - Pearl
Shea Joachim
Child - Sheriff
Molly Ann Carter
School Child
Patricia M. Peters
Web Girl
Matthias Hues
Oscar - Lion Tamer