Pee

Paul Reubens, who died at age 70 on Sunday, was best known for creating the character Pee-wee Herman, whose relatable childlike character was beloved by adults and kids of multiple generations. But his love of acting began in sixth grade, when he first hit the stage as Nick Burns in A Thousand Clowns at The Players Theatre in New York.

And as his career moved from stage to television and the big screen, where he reprised his beloved character throughout his life, he also starred in numerous films and television roles that showcased his range. From his most famous character to talk-show appearances, music video cameos, and roles in some classic films, here are some of the most memorable moments in his repertoire.

“This guy made me right here,” Paul Reubens as Pee-wee Herman says to the audience, about David Letterman during a July 5, 1983 episode of Late Night. Pee-wee made regular appearances on the show during the early 1980s, bringing props like weird toys and other curiosities, like a tissue box made from a doll’s head, or a newspaper to read personal ads aloud, and performing bits in front of a green screen, like the one in this clip where he takes Dave “for a ride in the country.” Letterman once theorized to The Washington Post, “What makes me laugh about this character is that it has the external structure of a bratty, precocious kid, but you know it’s being controlled by the incubus — the manifestation of evil itself. I think it has something to do with an important stage of embryonic development — some terrible intrusion or maybe a nutritional deficiency, I don’t know what exactly.” — Lisa Tozzi

As anyone who remembers that scene of Rapunzel’s prince bleeding out of his eyes can attest, Shelley Duvall’s Faerie Tale Theatre series was no stranger to the weird and macabre. Even in that context, however, there’s something of the uncanny in Reubens’ portrayal of Pinocchio in a 1984 episode of the series. Is it Joel Grey as the MC in Cabaret pancake makeup? The weirdly erotic way that his smooth plastic nose tumesces when he tells a lie? The nightmarish marionette sequence, or the fact that the two bullies in the film are played by a pre-Seinfeld and According to Jim Michael Richards and Jim Belushi? Either way, Reubens’ performance as the little wooden boy has the same mixture of creepiness and purity of heart that the American public would embrace with Pee-wee just a few years later. In any event, it clearly sets the stage for Pauly Shore’s yassified take on the role. —EJ Dickson

In the movie that made Paul Reubens a superstar and Pee-wee Herman a household name, Herman pursues his beloved bicycle, which his nemesis, the spoiled Francis Buxton, stole from him. The chase brings him to the Alamo (where he learns a valuable lesson), a biker bar where he dances for his life, the truck cab of Large Marge, and a Warner Bros. studio lot, among other scenic locales. The unwavering determination on Reubens’ face throughout, along with first-time feature-length filmmaker Tim Burton’s typically colorful sets, made the film hilarious and appealing to younger and older filmgoers, paving the way for the widespread success of Reubens’ TV show Pee-wee’s Playhouse. — Kory Grow

If you asked children in the late 1980s where they wanted to live when they grew up, “Pee-wee’s Playhouse” would have been a popular answer. With its surrealist geometry, psychedelic puppets, and inexhaustible, joyous surprises, the set was a dreamworld come to life — and Reubens, as manic Pee-wee Herman himself, was an adult who had somehow never stopped being a kid. While he imparted the usual lessons about kindness and empathy to his young audience on Saturday mornings, it was his infectious enthusiasm, as when he whipped the whole ensemble into a frenzy over the “secret word” of the day, that made the show a treat. And here, on his own turf, the most eccentric parts of Pee-wee’s life made perfect sense, whether it was getting hugs from a living chair named Chairry or that time he decided to marry a bowl of fruit salad (on a dare, naturally). In the end, what you really learned from Pee-Wee’s Playhouse was the value of a sense of humor. —Miles Klee

Three years after Pee-wee Herman traveled the country in search of his bike, he decided to settle down and … become a farmer. In the sequel to Big Adventure, Pee-wee Herman is a humble rancher leading a simple life with a pig and a fiancée (Penelope Ann Miller). But after a storm blows an entire circus, run improbably by Kris Kristofferson (playing Mace Montana), his interests soon shift to show business and the big top’s sexy trapeze artist (actress Valeria Golino). “It had to happen sooner or later,” Miller’s character tells Pee-wee, rolling her eyes. “You’re a man; she’s Italian.” But even when he’s breaking hearts, Herman engages in antics like practicing trapeze, sweet-talking a lion, and doing his “Tequila” dance on a tightrope. But even with the success of Pee-wee’s Playhouse on TV, the film unfortunately attracted middling reviews and underperformed at the box office. —KG

As the 1,200 year old Amilyn helping his master in his mission to turn a SoCal high school into a legion of vampires, Reubens takes what could have been a bit role and turns it into one of the funniest parts of the movie. Whether he’s “feeding” on David Arquette, or going hand-to-(one)-hand with Luke Perry, he holds his own. However the best scene may be his last, where Buffy (Kristy Swanson) finally takes him down — and he bounces and groans for a full 30 seconds before succumbing to his wounds. — Elisabeth Garber-Paul

The fantastical Halloween Town of The Nightmare Before Christmas wouldn’t be any fun without its creepy citizenry of ghouls and horrors, and few of these are menacing as a band of cackling trick-or-treaters assigned to abduct Santa Claus so Jack Skellington can take his place. Again working with a favorite collaborator in Tim Burton, Reubens voices Lock, a diabolical little red-headed boy whose devil mask (as are his companion’s witch and skull masks) is completely superfluous. He rounds out the trio with Danny Elfman and Catherine O’Hara, but seems to relish their brainstorm for how to torture “Sandy Claws” more than either when the gang breaks into one of the film’s catchiest songs. He’s one costumed brat you wouldn’t want to find at your doorstep after you’ve given away the last of your candy. —MK

Even as the straight man, Reubens can’t help but bring a little silliness to any role. In Matilda, Danny DeVito’s adaptation of the 1988 Roald Dahl novel of the same name, he plays an FBI agent investigating Harry Wormwood (DeVito), who’s running a stolen car-parts operation out of his garage. But you can see his brilliant physicality in his expressions, as the titular character (played by Mara Wilson) messes with his head by using her mind to move evidence as he searches their home. And you can see his most famous character come through as he runs down the street, slightly flailing, after she psychically sends his car careening down a hill. — EGP

Long before we were buried under a multiverse of Marvel slop, America was treated to a truly offbeat superhero satire for which it had no real frame of reference: Mystery Men was a flop when it came out in 1999, only becoming a cult favorite later on for its motley ensemble of wannabe crimefighters whose “powers” barely rise to the level of party tricks. Reubens, of course, was ideally pustulent as the grossest loser of the bunch, Spleen, so nicknamed for an ability to knock people out with precision-targeted farts. It’s a six-year-old’s kind of gag, so who else could pull it off? Spleen’s desperation to be accepted by his fellow outcasts — who do their best to avoid him — is matched only by the gleeful pride he takes in his vulgar ability. Pathetic, tasteless, obnoxious, and endearing all the same, Reubens’ performance here is what a goofball underdog comedy is all about. —MK

Few people buying tickets for Blow in 2001 would have expected to see Pee-Wee Herman playing a drug dealer opposite Johnny Depp, but when it comes to crime sagas, you need all the character actor firepower you can get — and Reubens delivers in one of his meatier film roles. That doesn’t mean he abandons his silly side, however: as Derek Foreal, a pot kingpin of Los Angeles, he pervs out upon first meeting trafficker George Jung (Depp), observing that the up-and-coming criminal “looks just like a Ken doll” after holding out the back of his hand for a kiss. Despite this awkward introduction, their business partnership becomes a driving force of the film, up to the inevitable betrayal. With his effete mannerisms and ironic detachment, Reubens effortlessly ushers us through the twilight of the hippies into the sleazy cocaine Seventies, a slippery, chameleon-like foil to Depp’s straightforwardly greedy outlaw. —MK

With a Snidely Whiplash ‘stache and a devious grin, Reubens played the ultimate baddie in the Raconteurs’ derby-themed video for “Steady, As She Goes”: He’s the malicious manager of racer Jack Lawrence and offers advice on how to beat Jack White’s favored “Copper Kid” in the Soap Box Challenge. “If we play it straight, there’s no way to beat this guy,” he cautions, before adding a mischievous pause, “…if.” All kinds of underhanded hijinks ensue, with Reubens sabotaging the drivers, pouring oil on the track and, finally, incapacitating the Copper Kid with a blow dart to the neck. It’s cartoon villainy at its most entertaining. — Joseph Hudak

Tina Fey reportedly wrote the role of Prince Gerhardt Hapsburg, the sickly, inbred Austrian prince who falls hopelessly in love with Jenna (Jane Krakowski) at his ill-fated birthday dinner, specifically for Paul Reubens, and it shows. Prince Gerhardt is a spiritual cousin of Pee-Wee: a deranged yet lovable naif whose optimism is just as incurable as his inability to metabolize grapes. Reubens delivers an unforgettably demented performance as the grotesque lovelorn prince, which is easily one of the top 5 celebrity cameos on 30 Rock, if not in the history of TV in general. —EJD

In the fourth season of Reno 911!, Reubens appeared as Lt. Rick of the Citizen’s Patrol. He’s basically the head of Reno’s Guardian Angels, complete with a red beret. When the sheriff’s department comes across a brutal homicide at an electronics store, Lt. Rick comes in and schools the police at their own job. He notices a missing cash register before they do, finds a single strand of wig hair near the corpse, and even manages to read a note from the killer in Thai. It’s yet more proof that Reubens was brilliant at creating characters even if he’s forever known to the world as Pee-wee. He returned to the world of Reno 911 in their 2007 movie Reno 911!: Miami where he played Sir Terrence, wealthy father of Nick Swardson’s character Terry. —Andy Greene

Paul Reubens makes a surprise cameo as a high-ranking member of the star-studded Vampiric Council during the first season of the hilarious FX show, What We Do In the Shadows. In the episode, “The Trial” the show’s four Staten-Island-dwelling main character vampires are brought before the council –—which also includes Wesley Snipes, Tilda Swinton, Evan Rachel Wood, Danny Trejo, and Taika Waititi — to face punishment for “premeditated vampicide.” All the actors on the council had portrayed a vampire previously in television or film — Reubens’ turn was in the 1992 movie Buffy the Vampire Slayer as Amilyn, follower of the local vampire king. —LT

After years of rumors and false starts, Reubens finally put the Pee-wee tux back on for the 2016 Netflix movie Pee-wee’s Big Holiday. Much like Pee-wee’s Big Adventure, the movie (produced by longtime fan Judd Apatow) finds the eternal child on a crazy road trip. This time around, he heads to New York City after Joe Manganiello, playing himself, invites him to his birthday party. Along the way, he meets up with an Amish community, bank robbers, and a weirdo that lives in a cave. It doesn’t quite live up to the magic of Pee-we’s Big Adventure, but it’s significantly better than Big Top Pee-Wee. It’s also a fitting final outing for Reubens’ most beloved character. —AG