Paul Reubens as Pee-wee Herman

Penelope Ann Miller as Winnie

Kris Kristofferson as Mace Montana

Valeria Golino as Gina Piccolapupula

Benicio del Toro as Duke the Dog-Faced Boy

Wayne White as Vance the Pig (voice)

Susan Tyrrell as Midge Montana

Albert Henderson as Mr. Ryan

Jack Murdock as Otis

David Byrd as Deke

Mary Jackson as Mrs. Dill

Frances Bay as Mrs. Haynes

Leo Gordon as Joe the Blacksmith (as Leo V. Gordon)

Anne Seymour as Pearl

Kenneth Tobey as Sheriff

Stephanie Hodge as Mermaid

Franco Columbu as Otto the Strongman

Kevin Peter Hall as Big John

Lynne Marie Stewart as Zelda the Bearded Lady

Dustin Diamond as Child - Deke

Jay Robinson as Cook

Kevin B. Kaplowitz as Child - Mr. Ryan

Jeffrey R. Shaw as Child - Otis

Marie Hawkins as Child - Pearl

Shea Joachim as Child - Sheriff

Molly Ann Carter as School Child

Myka Peck as School Child

Patricia M. Peters as Web Girl

Joey Arias as Shim

Helen Siff as

Matthias Hues as Oscar - Lion Tamer

Vance Colvig as Clownie

April Tatro as Human Pretzel