A fateful meeting with a mysterious stranger inspires Pee-wee Herman to take his first-ever holiday.
Paul Reubens
Pee-wee Herman
Joe Manganiello
Jessica Pohly
Pepper
Alia Shawkat
Bella
Stephanie Beatriz
Freckles
Jordan Black
Yul / Party Coordinator (voice)
Doug Cox
Mr. Murgatroyd
Linda Porter
Mrs. Rose
Monica Horan
Ruby the Crossing Guard
Brian Palermo
Marvin
Katherine Vanderlinden
Emily
Tara Buck
Beverly
John H. Mayer
Pharmacist
Richard Riehle
Dan
Dave Power
Dudley
Josh Meyers
Sylvester
Corey Martin Craig
Clovis
Paul Rust
Ernie
Robert R. Shafer
Construction Worker
John Moody
Daniel Lue
Police Officer
Darrin Henson
Clayton Cannon
Patrick Egan
Gordon the Traveling Salesman
Gloria Vassy
Panicked Female Passenger
Erick Chavarria
Panicked Male Passenger
Frank Collison
Clay
Lynne Marie Stewart
Jimmy
Karen Maruyama
Tourist at Snake Farm
Hal Landon Jr.
Farmer Brown
Michelle Meredith
Linda Brown
Meredith O'Leary
Louise Brown
K.T. Wiegman
Donna Brown
Julie Ouellette
Diane Brown
Alexandra Ella
Janice Brown
Mary Karcz
Betty Brown
Lily Mae Harrington
Pam Brown
Mackenzie Marsh
Judy Brown
Lindsay Hollister
Peggy Brown
Cooper Huckabee
Minister
Darryl Stephens
Rene
Dionne Gipson
Brook
Anthony Alabi
Lane
Sonya Eddy
Wanda
Diane Salinger
Penny King
Brad William Henke
Grizzly Bear Daniels
Leo Fitzpatrick
Abe
Christopher Heyerdahl
Ezekiel
Alan R. Rodriguez
New York City Policeman
Michael Pauley
Guy Who Bumps into Pee-wee
Joseph Mancuso
Pizzeria Employee
David Arquette
DJ
Janina Gavankar
Party Guest
Kelly Bush Novak
Taymour Ghazi
Nicole Sullivan
Shelly
Robert Broski
Abraham Lincoln
Pamela Mant
Queen
Thea Andrews
TV Reporter
John Paragon
TV Cameraman
Charles Robinson
Police Captain
Maya Nalli
Waitress
Deon Aumaier
Man with Toupee (uncredited)
Ryan Nemeth
Construction Worker (uncredited)
