Christmas at Pee-wee’s Playhouse, the 1988 primetime CBS special from comedian and actor Paul Reubens, is one of the strangest, most glorious, most improbable, most confident pieces of entertainment to appear on television. Thirty-five years after it aired, and in a period of reconsideration after Paul Reubens’s death, the Pee-wee Herman Christmas special still looks like one of the major pinnacles of Reubens as an artist, full of silly delight and winking subversion, all framed inside the relative safety of a big sparkly Christmas extravaganza.
Two years ago, Vulture editor Jesse David Fox and critic Kathryn VanArendonk discussed Christmas at Pee-wee’s Playhouse on their podcast The Specials, a Patreon project that digs into long conversations about comedy specials from the past. That conversation, which predated Reubens’s death, covers plenty of background and cultural context for the incredible oddness of Reubens’s project, especially the way it presents queer sensibility and pulls from Christmas specials and children’s television before it. In an excerpt from that episode below, Fox, VanArendonk, and podcast producer Jessamine Molli consider the legacy of Christmas at Pee-wee’s Playhouse, because it’s incredible to imagine it existing in 1988 on the brink of the American culture wars of the ’90s. Watching it now feels like, as Fox puts it, being in on a remarkable prank.
The full-length audio of this conversation is available for Patreon subscribers here.
Jesse David Fox: We’re talking about Christmas at Pee-wee’s Playhouse, the 1988 special that aired on primetime on CBS. Here’s some context: Paul Reubens joined the Groundlings in the mid-1970s, and in 1977 they did a show where different members of the theater created characters that were different types of people that might be performing at a comedy club. Comedy clubs were a pretty new invention at the time, but they were ripe for satire. Pee-wee Herman was the character that Paul invented because Paul couldn’t remember jokes and wasn’t good at telling them.
It was a freaking sensation, right away. By the 1980s, he was on television in character as Pee-wee Herman — on Cheech & Chong, on Mork & Mindy, and he was on David Letterman a bunch. In 1980, he auditioned for SNL but did not get it, and then dedicated his time to do a live Pee-wee Herman show that eventually became an HBO special. In 1985, his feature film Pee-wee’s Big Adventure was a huge hit, enough that he got a TV show, Pee-wee’s Playhouse in 1986, which was also a giant hit. This 1988 special came out right at the peak of how popular Pee-wee Herman was.
Kathryn VanArendonk: And Pee-wee wasn’t always a kids’ character.
JDF: The movie was for adults, and he had an HBO special. But then in 1986 he created a kid’s show. The bigger comedy context is that David Letterman was doing his thing, which was to blow up the idea of what a late-night show is while still doing a late-night show. 1988 is also when Hairspray comes out, when the John Waters camp aesthetic goes mainstream. CBS was airing Murphy Brown and Designing Women, but they also tried to bring back Dick Van Dyke — CBS was trying to be wholesome family TV.
But let’s just get it out of the way: This special is one of the gayest things I’ve ever seen.
KVA: Ever in my life.
JDF: And it should be noted, Reubens has never come out as gay. But, this special embodies a lot of those things that became identified with gay culture. It is undeniably queer, and it has all these gay touchstones in it. There was something about this special where he decided to go for every single possible reference he could.
Jessamine Molli: At the beginning with the list of all the celebrities who would be on the special, I thought it was a bit. Because obviously it was a joke that they could have that many celebrities. But it was not a bit!
JDF: In my notes about this special, I wrote “hahaha, how was this on TV.†This was a big opportunity, he’s getting network notes. But somehow, they were like, “Of course!†This weird mix of queer icons of the ’80s and camp icons of the ’50s, over and over again. Just the idea that people were watching this on CBS in the ’80s.
What’s so brilliant about it as a piece of queer art is that it is presented so earnestly, and the iconography they’re playing with is Americana. It plays as camp to our modern view of over-the-top earnestness. But it’s a mix of camp aesthetic and an alternative comedy aesthetic of laughing at bad jokes, like the series of fruitcake jokes, which were at the time a cliché, that fruitcake was bad. Why are we going to make this joke about fruitcake over and over again? Because it’s stupid!
KVA: There was more direct address in children’s television at the time, especially live-action direct address. But in this context, and given how much queer iconography was happening in the special, the fact that he’s looking directly at his audience is so bizarre. When my 4-year-old watched this with me, she was really trying to process it. She said, “He was looking at us. We can see him?†I could see her trying to process the strange intimacy of this incredible fantasy world he’s developing, and how blasé he is about it. The floor talks! There are googly eyes on every surface of this house.
JDF: Pee-wee’s Playhouse, the Saturday morning show, is more of a play on kids shows. Kids were able to watch it, but there’s also that feeling of the parents finally watching it and realizing, We were letting our kids watch this? But what’s so incredible about it is that because it’s a kids’ show, you’re allowed to play it straight, no pun intended. And it’s a Christmas special! It works because it’s played exactly like a regular Christmas special, and if you’re not up on queer iconography it just looks like a fun thing. It’s almost more fun watching it now that all these guest stars — like k.d. lang, Grace Jones, Joan Rivers — have such a different meaning in culture. It’s like a prank that we’re in on.
KVA: Some of that prank is because a lot of the audience would’ve been straight and had no idea what they were looking at. But so much of it is also enabled by being a Christmas special. Christmas is the place where you’re allowed to do big, sentimental things. You’re allowed to wear glitter, which is straight at Christmas time. It’s the time of year when we want things. We think about commercialism but also about emotions. You’re allowed to love people in soft, tender ways. It’s a cover, because Christmas is always a big performance we’re all putting on, whether or not we’re aware of that.
JDF: It opens with a military chorus singing a Christmas song. And then they start dancing! You get away with it. Who knows what a 1988 audience would’ve felt about it, but it is presented as silly and for kids, and not as clearly subversive.
The 1980s political context of Ronald Reagan is important, too, because of the 1980s fetishization of the 1950s, and Christmas at Pee-wee’s Playhouse is doing that too. It’s presenting Annette Funicello and the Del Rubio Triplets and the makeup and the big hair, with a real reverence toward them. You watch Drag Race now and the idea of a comedy queen is a person who looks like that. Why is that still the aesthetic of a type of drag queen? Because in the 1980s that art form is also codifying its language around this imagery.
But it’s also so hard because Reubens never came out, and he’s never talked about his work in this way. As a result, there’s this gap in how we think about the Pee-wee character’s role in this history.
KVA: There’s another angle of difficult territory here, especially in conjunction with the scandal that then defined Reubens’s career through the ’90s. It’s a children’s show, and he plays himself as a young innocent. There has been this panic about pedophilia as associated with queerness, and this moral panic about disrupted families and corrupted children. Even without explicit sexual abuse, the idea of queerness and being childlike, this intense panic about homosexuality — it’s not hard to see how a special like this could feed into exactly those narratives. So it’s so lovely to watch how absolutely non-dangerous this is, how gentle and silly and playful. But it’s also that much more surprising that it aired on TV.
JM: I don’t think about it as gay! But it’s because the merging of camp and queer culture didn’t exist to the same extent when I was watching it as a kid. It was just, This is bizarre. I love it.
JDF: And we’re watching it now, where queerness as an aesthetic is more mainstream.
KVA: Watching this now, though, I was thinking about how you can read Lord of the Rings and then read 12 other fantasy novels it inspired, and then go back to Lord of the Rings and note that they all feel relatively similar. You have to remember Lord of the Rings is important because it was the first one, but otherwise, they’re much of a piece. Pee-wee’s Christmas Special, by comparison, seems like the source of so much cultural iconography, and yet, nothing else around feels like this now. You can see Drag Race in it, but it doesn’t feel like Drag Race. You can see John Waters in it, but he’s his own thing.
JDF: The thing we’re not talking about is that he’s doing this character throughout, and Pee-wee Herman is a bizarre invention. This character, this annoying thing. A lot of comedians come up with an annoying boy character. I don’t know why it’s such a common trope, but this character was a sensation. He’s such a weird mix of knowing and not-knowing. Is it a boy or is it a man? There’s a moment in the special where he’s trying to open this safe, and he keeps looking over his shoulder to see if anyone’s watching, which is a very grown-up thing to do. Then when he opens his safe, it’s full of toys!
KVA: The special also has a gag about how long Pee-wee’s Christmas list is, and how many gifts he wants. There’s an underpinning of morality to it, a children’s lesson about how Pee-wee was too selfish and then he’s cruel to his friends (who are Annette Funicello and Frankie Avalon). At the end, Santa comes and shames Pee-wee about how much he asked for. You can almost feel some CBS executive watching it and thinking, This is okay! There’s a message!Â
JDF: Before then, you have a puppet named Randy who says, “Christmas is just a commercial exploitation by big business trying to capitalize on consumer guilt.†That is hard to imagine as a thing you’re seeing on CBS at 8 p.m. It’s so similar to parts of Bo Burnham’s Inside that it’s almost a direct allusion. But then he says, you forgot the true meaning of Christmas, and it cuts to an earnest story of Christmas about the Christ child! And Paul Reubens was Jewish!
So there is an undercurrent of the tradition of Jewish people making fun of Christian traditional values. This is the silly pageantry you guys do, and we as outsiders have gotten to witness it. It’s so silly. This is what you guys look like!
That feeling of, I can’t believe this was on CBS on 8 p.m. … There’s so much going on!
KVA: It’s so confident. There is no moment in this special where anyone flinches. And we see it as a subversion of a kind of Reaganism Americana, but it’s not really a subversion of the Del Rubio sisters. The k.d. lang performance here — it’s not meant to undermine country music as a genre. She’s reclaiming it, and she’s shifting the framing of it. She’s celebrating this particular form of expression, even as she’s saying there are other ways of entering into country music. The Americana is so intense that it’s hard to imagine making it if you didn’t also love it.
JDF: It’s a true camp aesthetic. It’s loving the bad things as much as the good things.
This interview was edited for length and clarity.
Listen to more of The Specials here.