He’ll always be best remembered as the man behind Pee-wee Herman, of course, but Paul Reubens’ legacy of laughter includes a vast number of additional characters, cameos, guest appearances and voiceover work. While fans and colleagues mourn his loss to cancer, we also wanted to make sure to celebrate the man behind Pee-wee and many of his other accomplishments. Here then is a look back at the most memorable moments from Reubens’ four decade career in film and on TV.
Before his original stage show, and long before starring in his own TV and movie projects, Pee-wee Herman was introduced to the world by none other than Cheech and Chong. The official first appearance of Pee-wee Herman to a mass audience came in the 1980 stoner comedy Cheech And Chong’s Next Movie as an annoying hotel desk clerk. Even at that early moment, he was already fully formed and recognizable as the character the world would later embrace.
After developing Pee-wee Herman during his time with Los Angeles-based comedy troupe The Groundlings, Reubens built a stage show around the character in 1981, with a supporting cast that included fellow groundling Phil Hartman. Unlike the more family friendly projects to come, the original Pee-wee Herman Show was more subversive, with an edgier sense of humor aimed at adults. It was so popular it attracted the attention of HBO, which filmed a performance and aired it as a comedy special.
Pee-wee hit the big time in 1985 with his first feature film, Pee-wee’s Big Adventure. It was also the debut of an up-and-coming young director named Tim Burton. The film retained many of the offbeat and childlike qualities of the stage show (you can’t have a Pee-wee film without the “big shoe dance”), while toning down the racier material to make it more palatable for a PG audience. It became an instant cult classic and thrust Pee-wee into the national spotlight.
Building on the success of the film, Reubens brought Pee-wee to television for Pee-wee’s Playhouse, a live-action series airing on Saturday mornings on CBS beginning in 1986. It had more in common with the stage show than the film, minus the mature content, and featured many of the same cast members, plus a young Laurence Fishburne as Cowboy Curtis. The show became a favorite of both younger and older viewers, and ran for five seasons before concluding in 1990, with a total of 45 episodes plus a Christmas special.
While filming Pee-wee’s Playhouse, Reubens somehow found the time to provide the voice for fan favorite RX-24, or “Rex,” the quirky StarSpeeder pilot droid who steered guests throughout the Star Wars universe on the Star Tours attraction, which opened in 1987. His role initially was uncredited, but it’s not hard to recognize Reubens’ signature inflections and laugh. After the attraction was redesigned in 2011 and C-3PO stepped in as the new pilot, Rex was moved to the cantina in Galaxy’s Edge, where he currently serves as the house DJ. He even popped up in an episode of the animated series Star Wars Rebels.
Ironically, it took his arrest for indecent exposure at an adult theater in Florida for Reubens to finally make a clean break from Pee-wee, but not before he infamously made a brief comeback appearance at the 1991 MTV Video Music awards just a couple months after the incident. Reubens, in his Pee-wee persona, received a standing ovation from the audience and was visibly moved by the warm reception. After laying low for a while, Reubens would go on to appear in major studio films like Mystery Men in 1999 and Blow in 2001 and started doing more interviews out of character as himself.
In one of his more notable post-scandal projects, Reubens played a supporting role as Amilyn, a loyal vampire servant of the powerful Lothos (played by Rutger Hauer), in the original Buffy The Vampire Slayer film. Sporting a goatee, frizzy hair, and heavy makeup, there’s no trace of Pee-wee in his menacing performance. He does get to do a bit of physical comedy, though, in his overly dramatic and prolonged death scene. He even returns in a post-credits scene to prolong it a little while longer.
Reubens earned his only Emmy nomination for a role that wasn’t Pee-wee Herman in 1995 for a recurring guest role on Murphy Brown. He played Andrew J. Lansing III, the unhinged nephew of network president Stan Lansing (Garry Marshall). Reubens’ Andrew is first introduced as one of Murphy’s (Candice Bergen) doomed assistants (it was a running gag that she’d get a new one each week, only to fire them by the end of the episode), but rather than being fired, he’s promoted to network executive. He later pops up as a mail boy, a producer, and a network vice president. Reubens appeared in a total of six episodes between 1995 and 1997.
Throughout the 2000s, Ruebens delivered a steady string of memorable guest appearances on network TV shows, including Everybody Loves Raymond, Ally McBeal, Reno 911!, and Pushing Daisies. His characters were often delightfully over the top, like Prince Gerhardt Messerschmidt Ramstein von Hoppe, a grotesque royal who takes a liking to Jenna in the 30 Rock episode “Black Tie.”
Reubens had a lucrative career behind the microphone, providing voices for several animated shows and movies. He seemed to particularly relish his role as Bat-mite, a fourth-wall-breaking superfan in Batman: The Brave And The Bold who tries to get the show canceled. He would return to voice Bat-mite again in Lego DC Comics: Batman Be-Leaguered. By that point, Reubens was already a Batman veteran, having played the Penguin’s father in 1992’s Batman Returns.
After putting some distance between himself and Pee-wee for the better part of a decade, Reubens was finally ready to revive the character in 2010. He brought his alter-ego back to the stage in its original incarnation as The Pee-wee Herman Show. There were a few updates to the material, but for the most part it followed the previous script and kept its deviant sense of humor intact. It sold out its initial two-month run at the 7,000-seat Nokia Theater in Los Angeles (now known as the Peacock Theater) and transferred to Broadway in 2011.
Around the same time the stage show returned, Reubens appeared as Pee-wee in a sketch for Funny or Die. In it, he shows off a brand new iPad, which had just hit the market for the first time, and interacts with the various puppet characters on the familiar Playhouse set. Amazingly, if it weren’t for the iPad in Pee-wee’s hand, it would seem like no time has passed at all.
Riding a new wave of Pee-wee popularity, Reubens teamed up with Judd Apatow and Paul Rust to make a third film, Pee-wee’s Big Holiday, for Netflix in 2016. The long-awaited follow up to 1988’s Big Top Pee-wee, it finds our hero inspired by actor Joe Manganiello (playing himself) to expand his horizons and go on adventure outside of his small town. Reubens has admitted that he got some assistance from de-aging technology, but after all those years, the Pee-wee suit still fit him like a glove.
Following an arc in a few episodes of the DC show Gotham, Reubens returned to the fold once again in 2018 to play Mike the Spike, a serial killer with the ability to possess inanimate objects (the official terminology is dybbuk), on DC’s Legends Of Tomorrow. After inhabiting various dolls and puppets with murderous intent, he’s eventually defeated by the Legends and winds up as an entertainer at a magical theme park.
Pee-wee Herman wasn’t the only character Reubens returned to in recent years. In a 2019 episode of What We Do In The Shadows called “The Trial” he played one of the members of the Vampiric Council, bearing a striking resemblance to Amilyn from Buffy The Vampire Slayer (the facial hair and makeup are unmistakable). It was one of many fun cameos by various actors who have played vampires over the years, all going by their real names.