A fateful meeting with a mysterious stranger inspires Pee-wee Herman to take his first-ever holiday.
Paul Reubens
as Pee-wee Herman
Joe Manganiello
as Joe Manganiello
Jessica Pohly
as Pepper
Alia Shawkat
as Bella
Stephanie Beatriz
as Freckles
Jordan Black
as Yul / Party Coordinator (voice)
Doug Cox
as Mr. Murgatroyd
Linda Porter
as Mrs. Rose
Monica Horan
as Ruby the Crossing Guard
Brian Palermo
as Marvin
Katherine Vanderlinden
as Emily
Tara Buck
as Beverly
