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

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

Patricia M. Peters

Web Girl

Joey Arias

Shim

Helen Siff

Matthias Hues

Oscar - Lion Tamer

Vance Colvig

Clownie

Tai the Elephant

Circus Elephant (uncredited)