Pee-Wee’s inventory of content for a loyal fan base includes a lot. With a trilogy of feature films, 46 episodes of Pee-Wee’s Playhouse, and two live shows separated by thirty years, Paul Reubens could easily retire as an accomplished pop-culture icon, but nobody wants that. When the third Pee-Wee Herman film was in development, there was talk of the plot revolving entirely around the characters established in Pee-Wee’s Playhouse. There were even details revealed about the characters no longer confined to the Playhouse and traveling to get back home. While Big Holiday certainly delivered an excellent adventure filled with signature Pee-Wee humor and offbeat characters, there’s something wildly imaginative awaiting should Reubens stay the course and get the Playhouse movie made.

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Pee-Wee’s Playhouse is really the only concept that Reubens ever revisited on more than one occasion. Pee-Wee’s Big Adventure and Big Top Pee-Wee represent two distinctly different cinematic universes, with Big Holiday establishing a third unique world where the character resides. Revisiting the Playhouse with a movie set in modern times could introduce hilarious self-referential opportunities for the comedic legend to give fans something truly special and totally bizarre. With a tongue-in-cheek revisit to the Playhouse, where we find a truly grown-up version of Pee-Wee, there is no shortage of comedy gold to be found. Embracing the fact that Paul Reubens is approaching 70, there’s a unique opportunity to conceive a more mature script that plays to his fan base, who are all grown up now.

Let us ponder a return to the Playhouse that isn’t quite as kid-friendly as it used to be.

Pee-Wee’s Golden Years

     Netflix

While going hard R is probably a mistake, there are ways a modern take on Pee-Wee’s Playhouse could lean heavier into the adult themes that occasionally showed up in the TV show. This could be particularly funny in imagining more rugged versions of his playhouse pals like Chairry, Globey, Magic Screen, and Randy. Right off the bat, the death of a puppet character like Mr. Window could bring a laugh that also packs some emotion. Sadly, we lost John Paragon last year, who played Jambi, but perhaps he was just a figment of Pee-Wee’s imagination all along. All of it could potentially be framed in such a way if the script ventures into Kaufmanesque territory, which is not outside the realm of possibility.

With themes of losing and finding your inner child, growing up, rites of passage, etc., there is a ton of drama and comedy potential that Pee-Wee could exploit in his golden years. While Reubens has made an effort to maintain a youthful appearance of the beloved icon for years, a sudden reverse on this policy could really grab the attention of media and fans alike. Also, the idea of the Playhouse characters not being confined to that particular set is wonderfully strange to imagine.

Others Who Broke Form

     Shout Factory

1995’s Brady Bunch Movie was a risky proposition but ultimately proved successful by placing the 1970s show into the modern ’90s era as a self-referential plot device. 1987’s Dragnet brought the serious 1960s show onto the big screen in the form of a comedy which went over well with audiences. 21 Jump Street from 2012 made the wise decision to repurpose the late ’80s TV drama into a straight comedy proving to be incredibly successful worldwide. Many of these TV-to-movie projects spawned sequels as well. While the concept certainly calls for the right comedic writer and director to make it work, the Playhouse movie would surely pack a provocative punch in the 2020s, giving Reuben’s the opportunity to explore the material through a new lens.

More successful shifts from TV to cinema include Star Trek, Twin Peaks, The Addams Family, Mission: Impossible, The Naked Gun, and The X-Files, just to name a few. Pee-Wee’s Playhouse was likely the result of Big Adventure being a hit, so there is a certain full-circle irony if Playhouse were to become a movie. At the height of the show’s success, Reubens somehow managed to squeeze in Big Top Pee-Wee, a love letter to rural America and the circus for which Reubens clearly has a great affinity.

The Hollywood legend has successfully maintained an enigmatic presence in the media and survived a pre-internet-culture cancellation attempt in 1991. In recent years, he has appeared numerous times with late-night talk show hosts, especially Conan O’Brien, to share more about himself. His presence always seems to be accompanied by a well-thought-out gimmick, comedic angle, or unexpected shtick. He recently shared his love of collecting strange things on Conan and landed a one-off radio show on KCRW after a social media stunt. He often uses social media to highlight absurd and quirky content that resonates with him.

While a Playhouse movie remains speculative, the actor has mentioned completing a new Pee-Wee script in 2020 while chatting with O’Brien about a childhood tea party with his father. Fans can remain hopeful that a new Pee-Wee project will likely be announced in the future.