Genre: Drama/Comedy/Biography
Director: Michel Gondry
Writer: Chad Taylor
Cast: Paul Dano, Rooney Mara, Ned Beatty, Julie Christie, Matt Lucas, BJ Novak, Lily Rabe, John Cena
Plot: Pee-wee Herman (Paul Dano) sits alone on the set of Pee-Wee’s Playhouse, his TV show. The studio lights are being turned off one by one, having just filmed the last episode of the show. Herman is clad in his signature grey suit that’s a size too small and a bright red bow tie. As the light technician exits, Pee-wee wishes him well. As the last one in the studio, Pee-wee says goodbye to his playhouse. His talking furniture tell him they will miss him.
During the opening credits, he rides his red Schwinn bike on his commute home. Passerbys wave at him and he waves back but keeps on riding. At home he hangs up his bike on the wall of his garage and shuts the door. Pee-wee becomes restless from boredom. Finally, he receives a phone call inviting him to dinner tonight and he jumps at the opportunity.
Before he leaves, he considers taking his Schwinn but decides instead to take a taxi. The taxi drives him to one of the biggest mansions in Beverly Hills. He is greeted at the door by a butler Bernard (Matt Lucas), who he is on a first-name basis with. Bernard takes him to the dining room, where he is met by the homeowner Doris (Julie Christie). Doris looks to the camera and acknowledges that some of the audience may be confused so she’ll try to recap (a sped-up slideshow accompanies her words):
Pee-wee Herman was born on the comedy circuit of the early 1980s and gathered a small following with his boyish mannerisms and mischievous demeanor. This then turned into two cult television shows and two hit movies. And this was exhausting to Pee-wee, who decided to take a temporary hiatus from the public eye.
A younger woman named Chandi (Rooney Mara) then approaches and kisses Pee-wee on the cheek. He blushes and looks to the camera in embarrassment. He says this will take some more explaining:
After several failed marriages and a miscarriage, tobacco heiress Doris Duke found herself increasingly lonely heading into her twilight years despite being the richest woman in the world. After a chance encounter, a friendship blossomed between belly-dancer/Hare Krishna follower Chandi and the two became inseparable as they traveled the globe. Doris adopted Chandi, convinced that she was the reincarnation of her infant son. At a high-profile party, Doris and I bonded over our mutual obsession over 1950s footwear and I’ve been a close family friend since that day.
At the table, Doris and her guests ask Pee-wee about his newfound retirement and he becomes anxious. His forks and knives come alive and ask him why he left his Playhouse playmates alone in the dark and he starts sweating. Overwhelmed by the voices, he yells at them to stop – causing the dinner guests to all look at him in confusion. He does his signature laugh (in a and takes the spoon and, as a delay tactic, spins the spoon into a ring. He then gets down on one knee and proposes to Chandi. Chandi nervously laughs until she seems to connect with Pee-wee’s visual cues and starts to go along with it. Everyone at the table starts congratulating them, although Bernard watches with a suspicious eye.
Chandi accompanies on his drive home and Pee-wee takes the “ring” and throws it out the window. They laugh about it and she apologizes for the way her family and friends acted towards him. He says it is no big deal, he is just not sure if he is ready to answer the “what’s next” question. When they arrive at his house, an obsessive fan dressed up as Pee-wee is waiting in the drive-way. The fan asks for an autograph but Chandi is quick to act and demands that the fan leaves or she will call the cops. The fan says he is glad Pee-wee’s show was cancelled, spits at him, and runs off. Pee-wee mumbles to himself that it wasn’t cancelled.
Chandi is concerned for her friend and suggest that they take a vacation to Hawaii. A comedy montage commences as Chandi and Pee-wee explore Hawaii. Over the course of the montage (despite being only a week), Pee-wee grows his hair out long and exchanges his tight suit for a halfway-buttoned Hawaiian shirt. When checking out of the hotel, the clerk asks for his room number and she asks if he is Pee-wee. He says no, “my name is Paul”. He puts sunglasses on a leaves the hotel.
Back in LA, we see Paul’s new-found confidence in action. He walks down the street and no one recognizes him and he takes this in stride. He plays high-stakes poker, binge-drinks at bars and visits strip clubs. At the strip club, he runs into famous comedian Phil Hartman (John Cena). Pee-wee turns to the camera to explain but Phil interrupts him, offering to keep it short and sweet:
We were friends. I helped Pee-wee get famous. I never got credit for it. It’s whatever.
They nod their heads at each other and continue on their way, clearly not as friendly as they once were. Paul’s excursion is interrupted when he gets a phone call from his father Lon, telling him that his sister-in-law is in labor and he would like him to come home to see his nephew. Paul hems and haws about it but decides to go.
In Florida, Paul’s family greets him with open arms. Lon (Ned Beatty) is a bit over-aggressive as he has always been but still warm. His brother Todd (B.J. Novak) and his wife Jolene (Lily Rabe) are exhausted from the last few days and Paul introduces himself to their newborn. When everyone returns to Lon’s house, they catch up. Todd talks about the stress of his job and Paul teases him about his receding hairline, calling him a has-been. Todd turns the tables and says “I know you are but what am I?” – one of Pee-wee’s famous catchphrases. Todd then asks how things have been since giving up the Pee-wee act. Paul, nervous, looks around at the household objects but they remain motionless. He then talks about how nice it has been to be able to act like an adult for once instead of maintaining the image of a squeaky-clean prepubescent boy. They share a laugh about it. In private, Lon tells him that he hopes that this break from showbiz means he’ll be able to visit home more often.
Chandi calls Paul hysterical and says that Doris has grown disgusted with her and disowned her. She says that Doris accused her of using Paul for his fortune and fame and taking advantage of his vulnerable state. She is adamant that this is not true but he connects the dots and thinks it might be the case. They hang up the phone call with the issue unresolved.
A frustrated Paul goes out on the town and is cruising the streets with his hair flowing in the wind. He passes an adult theater and then reverses back to it and parks. When he goes inside, the camera stays on an exterior shot of the theater as time starts to rapidly pass. Finally, in the wee hours of the morning, Paul is walked out of the theater with handcuffs on and followed by two undercover policemen.
When he gets out on bail, Paul is horrified to find that his worst nightmares have been realized: Pee-wee Herman and Paul Reubens have merged and all the news outlets are talking as if Pee-wee Herman was arrested for indecent exposure. He visits his father, who he sobs into the lap of. He is angry at himself for letting himself thinking the two worlds would never meet. Todd brings over his young daughter to try and cheer Paul up.
Weeks pass and tons of photographers and journalists remain huddled outside of Lon’s home. Paul remains isolated there when he keeps getting calls from Chandi. Finally, he listens to a shocking voicemail: Doris has had a stroke and passed away suddenly. Paul knows that he finally has to get out of the house as Doris was his close friend. When he leaves, he knows he has to cut his hair and revert back to his Pee-wee outfit.
At the funeral, dozens of paparazzi lurch trying to get pictures of Pee-wee. He and Chandi are met by a solemn Bernard, who is devastated. Chandi is sad that she didn’t get the chance to say goodbye to her mother. When they arrive at Pee-wee’s home, Chandi makes an enquiry into Doris’s will and discovers that she was left out of it entirely. She received nothing of the $1.2 billion inheritance.
This situation intrigues Pee-wee and he feels that something is up. Determined to feel useful, he decides to help Chandi investigate Doris’s death. They discover that her will, which had been revised 5 times over her lifetime – was last changed a week before her death. The sole recipient of her fortune is the Doris Duke Charitable Foundation. More research into that finds that that foundation was founded that very day. They write down the address of the organization and Pee-wee offers her a ride on his Schwinn bike.
When they arrive at the building, they find the door unlocked to Foundation’s office. It is a bare room with only a desk and a few pictures on the wall. All of the pictures are of Doris and her butler Bernard. An actual lightbulb appears above Pee-wee’s head and he posits that Bernard viewed Chandi (and Pee-wee, through their fake marriage) as a competitor for Doris’s fortune and that he intentionally caused a rift between Doris and her daughter so that the notoriously fickle Doris would exclude her from the will. They both look at the camera and ask “But how did Doris really die?”
Bernard sits on a sunny beach, surrounded by servants and flaunting an expensive outfit. He smiles at the camera:
I was incredibly saddened by Doris’s death. Sure, I was quick to spend my newfound wealth but who wouldn’t be? Multiple people tried to sue me but I always ended up on top. The death was never found to be suspicious. Perhaps they were just jealous of my ability to play the long game? Oh well, I die three years after this, anywho. Might as well live it up while I can.
Pee-wee hugs Chandi, realizing that she wasn’t trying to take advantage of him after all. He tells her he has to go back home now. When he arrives in Florida, he tells his family that he is grateful for supporting him along the way. His father suggests that he sell his house in California and live here, out of the spotlight, for a while. He accepts the offer, saying this is the one place where he truly feels himself. Lon tells his son "Do not define yourself by what other people think of you."
His father then says he almost forgot to show him something. They go to the kitchen where dozens of cards are awaiting Pee-wee from various friends, celebrities and relatives. They are all supportive of the man they know him to be. All of this warms his heart. He gives Phil Hartman a call and apologizes for them growing apart over the years.
He goes to his room and hangs his Pee-wee outfit up in the closet. He looks at it with a bittersweet smile when the bed in the background whispers “someday”. He looks back but everything is motionless. He looks at the camera and shrugs his shoulders.
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