At home in his Puppetland playhouse, Pee-wee entertains his audience of "boys and girls" in a homage to low-budget 1950s’ TV kiddie-shows such as Howdy Doody and Pinky Lee.
Pee-wee Herman has a heavily accessorized bicycle that he treasures and that his neighbor and enemy, Francis Buxton, covets. A bike shop employee, Dottie, has a crush on Pee-wee, but he does not reciprocate it. Pee-wee's bike is stolen while he is shopping at a mall. The police tell Pee-wee that they cannot help him find his bike. Pee-wee thinks Francis took it, and confronts him. Francis' father convinces Pee-wee that Francis did not steal the bike. Pee-wee then offers a $10,000 reward for his bike. Francis, who did indeed pay to have someone steal the bike, is frightened by Pee-wee's relentlessness and then pays to have it sent away. After holding an unsuccessful meeting to locate the bike, Pee-wee angrily rejects Dottie's offers of help. Desperate, he visits "Madam Ruby", a phony psychic. Ruby, inspired by the Al and Moe's Bargain Basement shop across the street, tells Pee-wee that his bike is in the basement of the Alamo Mission in San Antonio. Pee-wee hitchhikes to Texas, getting rides from a fugitive, Mickey; and from Large Marge, the ghost of a deceased truck driver.
Each show, Pee-wee Herman comes to his wonderful playhouse where anything can happen. Whether it be screaming at the secret word, entertaining friends like Cowboy Curtis and Ms. Yvonne, or enjoying animation clips presented by the King of Cartoons or the stories of the claymation girl, Penny; there's always lots of fun things to do.
The film starts in a dream sequence. Pee-wee Herman has a dream of being a famous singer. Avoiding his fans, he makes his exit by disguising himself as Abraham Lincoln. One of the fans asks him for his autograph, but his disguise is promptly exposed. They chase after him and he flies off to his ranch. Pee-wee finally awakens from his dream that morning to work on his farm with Vance the pig (Wayne White (artist)). Later, he has lunch with his fiancée, school teacher Winnie Johnson (Penelope Ann Miller). Next, he races Vance to a general store owned by Mr. Ryan (Albert Henderson (actor)) to order a cheese sandwich.
Subversive humor and childlike wonder based on both Reubens' original stage show, "The Pee-wee Herman Show," and the Emmy-winning Saturday morning TV show, "Pee-wee's Playhouse."
Pee-wee Herman is a resident of the small town of Fairville and works as a cook at Dan's Diner, where he is well liked by the locals and revered for his cooking. He meets and befriends actor Joe Manganiello, who convinces Pee-wee to leave Fairville for the first time in his life to travel to New York City and be a guest at Joe's birthday party.
