Paul Reubens Pee-wee Herman Jordan Black Yul / Party Coordinator (voice) Doug Cox Mr. Murgatroyd Linda Porter Mrs. Rose Monica Horan Ruby the Crossing Guard Brian Palermo Marvin Tara Buck Beverly Richard Riehle Dan Dave Power Dudley Josh Meyers Sylvester Corey Martin Craig Clovis Paul Rust Ernie Robert R. Shafer Construction worker Joe Manganiello Joe Manganiello Stephanie Beatriz Freckles Alia Shawkat Bella Daniel Lue Police Officer Darrin Henson Police Officer Clayton Cannon Police Officer Frank Collison Clay Lynne Marie Stewart Jimmy Karen Maruyama Tourist at Snake Farm Hal Landon Jr. Farmer Brown Cooper Huckabee Minister Brad William Henke Grizzly Bear Daniels Christopher Heyerdahl Ezekiel David Arquette DJ Janina Gavankar Party Guest Nicole Sullivan Shelly Charles Robinson Police Captain (as Charlie Robinson)