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