The kooky Christmas At Pee-wee’s Playhouse remains a holiday special for the fruitcake in all of us

Let's look at one of the most beloved television specials from one of the most beloved children’s television shows of the ’80s, which was bursting with so much queer content that it honestly feels inaccurate to simply call it “coded.”

Image Credit: ‘Pee-wee’s Playhouse Christmas Special,’ Image Entertainment

Welcome back to our queer film retrospective, “A Gay Old Time.” In this week’s column, with Christmas fast approaching, let’s revisit one of the queerest holiday specials ever, 1988’s Christmas At Pee-wee’s Playhouse.

The history of holiday-themed queer entertainment isn’t necessarily the most vast or extensive one. Because Christmas (and Christmas-adjacent) movies tend to be so family-focused, and for so long we were treated by mainstream Hollywood as the antithesis of those values, we were never featured in them, or were relegated to minor supporting roles. (You could program a small film festival solely with holiday movies with a queer, usually neglected sibling or family friend as part of the ensemble.)

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It wasn’t until recently that we started appearing front and center in the family units that these movies usually revolve around. Before then, it was up to us to either create alternative, independent festive films, or to read between the lines (as we were trained to do with all other types of media) to find ourselves hidden in the entertainment everyone else can enjoy more openly.

This week, with Christmas right around the corner, we’ll look at one of the most beloved television specials from one of the most beloved children’s television shows of the ’80s, which was bursting with so much queer content that it honestly feels inaccurate to simply call it “coded.”

The Set-Up

Image Credit: ‘Pee-wee’s Playhouse Christmas Special,’ Image Entertainment

Pee-wee’s Playhouse ran on CBS for five seasons from 1986 to 1990 for a total of 45 episodes. The brainchild of Paul Reubens, who created the character of Pee-wee Herman through his stand-up & sketch comedy career, the show was a warped and incredibly innovative take on children’s programming, blending a traditional Sesame Street-style variety format with edgy alternative comedy, intricate character work, stop motion and 2D animation.

Almost forty years later, we have a greater understanding of Paul Reubens and the character of Pee-wee, mainly due to the incredibly insightful two-part docuseries Pee-wee as Himself that premiered on HBO earlier this year. The project officially confirmed the much rumored claim that Reubens was a gay man, and invites us all to see Pee-wee and his world as a direct extension of his queerness: a way for him to turn “otherness” and “weirdness” into an artistic expression that appealed to millions of viewers.

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Stockings Stuffed With Stars

Perhaps nowhere is this more clear than with Christmas At Pee-wee’s Playhouse, the one-hour holiday special that aired on December 21, 1988. The “plot” of this special is quite straight-forward, and should be familiar to anyone that ever watched any similar programs: Pee-wee is getting ready to celebrate the holidays, and throughout our time with him, he’s visited by a cavalcade of characters and celebrities who drop by to wish him well, or participate in some joy-spreading activity.

There’s of course the regular cast of human and animated/puppet characters that populate the Playhouse: Pee-wee wishes for Christmas decorations with Jambi (John Paragon), ventures into the snow with Cowboy Curtis (Laurence Fishburne), receives holiday mail from Reba the Mail Lady (S. Epatha Merkerson), and learns about Navidad from Ricardo (Vic Trevino), among many others. The word of the day is “year” and there’s a delightful running gag about him getting nothing but fruitcakes (double-entendre intended, right?).

But the list of celebrity guests that pop by is a true queer fever dream that could easily double as a guest list for Studio 54 in the ’70s. Frankie Avalon and Annette Funicello are bullied into making five hundred holiday cards with arts and crafts! Magic Johnson takes a sleigh ride with Pee-wee! Little Richard wants to ice skate! Whoopi Goldberg and Oprah Winfrey call to leave their good wishes! Charo shows up to sing “Feliz Navidad”! Grace Jones shows up to sing “The Little Drummer Boy”! Cher is there to announce the word of the day…!

Making The Yuletide Gay

Image Credit: ‘Pee-wee’s Playhouse Christmas Special,’ Image Entertainment

There was always an element of absurdism and surreality inherent to Pee-wee’s Playhouse. Although aimed at young children, the level of comedy and artistry pointed to an elevated sense of sophistication and complexity underneath (something the docuseries really delves into in-depth). It’s not meant to be straightforward and purely educational, but it’s also not quite a parody or spoof. There’s an earnestness in how it always leaned into being different, subversive, and unafraid to perhaps be misunderstood. At its core, the character if Pee-wee and the world he inhabits were inherently queer.

But the already strange elements really take off in the Christmas special. Having so many A-list stars come together (in moments that are essentially blown-up cameos) in an environment that feels so alien and yet not questioned by them at all feels like stepping into an alternate reality. It brings amusement and confusion at the same time, which is the lens a lot more entertainment should be looked through. 

The special takes a well-known and traditional (and by that point, quite dated) television format, puts it in a kaleidoscope, shakes it up and serves us whatever comes out the other end. It’s the clear, singular vision of an artist who understood what it means to feel different, who created a safe space (long before that term evolved into all the connotations that it’s associated with today) where strangeness was the norm, and who saw the inherent joy in having Joan Rivers appear on-screen for three seconds just because he could.

For The Fruitcake In All Of Us

Image Credit: ‘Pee-wee’s Playhouse Christmas Special,’ Image Entertainment

Christmas At Pee-wee’s Playhouse provides an unexpected entry in a genre that is still so hard for the queer community to see themselves in. Though we’re not relegated to the corners of the family table like we used to be, the special’s not as outwardly “about” us as some of the holiday programming you’ll see while surfing Netflix or The Hallmark Channel these days.

And yet it’s a fascinating middle point: a show that is so clearly and unapologetic for us & by us (our tastes, our sensibilities, our sense of community, family, and whimsy), but one that still hides behind a formula that lets us into the homes of millions. And it’s a reminder that Pee-wee’s biggest legacy is to give us permission to simply just play. What a great way to go into the new year (cue screaming because “year” is the secret word of the day).

The full Pee-wee’s Playhouse Christmas Special is available to stream for free via the official Pee-wee Herman YouTube page.

You can keep track of all LGBTQ+ films covered in our A Gay Old Time column via writer Jorge Molina’s handy Letterboxd List.

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