There was no time of the day that Pee-wee Herman couldn’t entertain on television. But it was in late night, specifically Late Night with David Letterman, that Paul Reubens truly launched his character into the zeitgeist.
Reubens’ affable Pee-wee, who presented like a childish Mister Rogers but possessed a wit worthy of Paul Lynde, was developed in the wake of his rejection to join the ill-fated 1980-81 season of Saturday Night Live. The former Groundlings member took his Pee-wee Herman character to the stage in Los Angeles, presenting The Pee-wee Herman Show as a “live onstage TV pilot.” A tour and an HBO special soon followed.
Had he arrived earlier, a character like Pee-wee would not likely have found a home on late night television. But the innovative, meta nature of the character fit in perfectly with the brand of comedy David Letterman brought to network television with Late Night in 1982.
Reubens made his Late Night debut on September 22, 1982. The host introduced him with a simple qualification: “you’re not going to see anything like this gentleman anywhere in the world.”
To put into words a Pee-wee Herman performance is a nearly impossible task. It is an audiovisual experience: from the cadence and pitch of his voice to the slight twists and turns of the body that run down from his eyebrows to his feet. The cheery demeanor accompanied by devastating eyerolls. And, of course, the reactions of his audience. From the moment he walks out, Dave begins to laugh, clearly relishing the chance to witness a brand of brilliant, absurdist comedy not unlike his own.
Before Dave even has a chance to start the interview, Pee-wee launches into a story about a lemonade stand he operates outside his house whenever he is not hosting his own show:
Mr. Letterman came in yesterday and I was sitting there, and he goes, ‘Hi Pee-wee how you doing?’ And I said, ‘Fine Mr. Letterman. How are you?’ And he goes, ‘Good.’ And then he goes, ‘While you’re in New York why don’t you do the show?’ [slight chuckle, turn of the shoulders] I couldn’t believe it, because that’s what I was here for. I mean what else would I even been doing here?
“You cracked me up yesterday,” Pee-wee added. “I didn’t even get to tell ya.” Letterman looks wonderfully lost for words.
That performance would be the first of nearly a dozen visits that Pee-wee would make with Dave. In fact, Pee-wee would return to Late Night the following month, and make five appearances the following year.
On July 5, 1983, he even took Dave for a drive, and that’s our stop on this week’s Late-Night Time Machine.
Pee-wee’s visit that night begins on a rather sweet note, as he comes dashing out to give Dave a gift made by his sister, Hermione Herman: a tissue box made from the head of a doll. “You can use it for a lot of things,” Pee-wee says, before sneezing directly into his hand and plucking a tissue from the head.
He goes on to bring out a newspaper from a recent trip to Minneapolis. He reads a dating add put in the paper by a man, who shares that he is looking for a partner who, among other things, shares a similar comedic sensibility, enjoying acts like “Pee-wee Herman.” He is thrilled and honored by such an ad. “You know it’s from your show too. This guy made me right here! Me and Dave are like this,” he says, crossing his fingers to applause from the audience.
As a sign of his friendship, Pee-wee came equipped with a special effect. Knowing Dave had to work the day before, which was the Fourth of July, he figured his pal might enjoy going for a nice summer ride in the country. The two then sit in front of a green screen, Dave in the passenger’s seat as Pee-wee holds up a steering wheel and takes them for a drive.
Pee-wee begins to grunt and squeal in delight, turning the wheel and smiling from ear to ear as the car takes off. Dave is laughing so hard he can barely stay in the frame. Pee-wee launches into a story but is quickly derailed by video of the car behind him: “this guy is right on my butt here.”
The pair speed ahead, tires squeaking all the way, their seats bobbing up and down. “Dave, take the wheel!” Pee-wee exclaims, handing it over to Letterman. Pee-wee then takes back the wheel, swerving to avoid “giant” puddles. Just before Letterman throws to a commercial break, Pee-wee gets carsick and vomits outside the frame.
The simplicity of the concept. The novel backdrop. It all blends perfectly with the way Pee-wee relishes the chance to exist with his audience in an unclear emotional state: are we to laugh, cringe, pity? All and more? None? To watch the scene recalls another, even greater bit with a similar concept: Dean Martin and Jonathan Winters as airline passengers on The Dean Martin Show. When the latter passed in 2013, Reubens wrote, “Jonathan Winters was an influence on so many and there was nobody like him.”
By 1984, Reubens would take his talents to The Tonight Show Starring Johnny Carson, with Joan Rivers in the host’s chair. Reubens became a friend and a favorite of Rivers, even appearing as one of first guests on her FOX program, The Late Show Starring Joan Rivers.
Though his frequent appearances as Pee-Wee Herman with David Letterman ground to a halt in 1985 (he returned to guest as himself some 15-plus years later), Reubens continued to appear on shows across the late-night landscape throughout the rest of the career, winning fans from viewers and hosts alike.
“No tweet can capture the magic, generosity, artistry, and devout silliness of Paul Reubens,” Conan O’Brien wrote after Ruebens’ death in 2023. “His surreal comedy and unrelenting kindness were a gift to us all.”
The ups and downs of Paul Ruebens’ life and career are the subject of the new two-part documentary Pee-Wee as Himself, premiering tonight on HBO.
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