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

Helen Siff

Matthias Hues

Oscar - Lion Tamer

Vance Colvig

Clownie

April Tatro

Human Pretzel

Tai the Elephant

Circus Elephant (uncredited)