The Pee-wee’s Playhouse Christmas Special put a fresh coat on an old format

You already know the 12 Days Of Christmas, with its drummers drumming and partridges and gold rings, but we here at The A.V. Club like to take everything one step further, for your reading pleasure. Hence, 13 Days Of Christmas, a collection of essays on a handful of beloved holiday classics and a few that have sadly fallen through the cracks. Up today, the 1988 Pee-wee Herman holiday spectacular.
The Pee-wee’s Playhouse Christmas Special aired almost 25 years ago on CBS, and I still know every word to the opening song. More than that, I know almost every detail about the whole special, from the words of Dinah Shore’s bonus verses to “The 12 Days Of Christmas” to Pee-wee’s frustrated blundering of “Merry Christmas” in Spanish, or as he puts it, “Feliz Nabiblah.” More than anything, though, I remember the special’s general sense of happy absurdity. Pee-wee Herman—or maybe, more specifically, the idea of Pee-wee Herman—had the power to get big celebrities to make idiots out of themselves, and to do so happily.
The traditional network Christmas special held that power, too. These mostly extinct programs brought people together for a festive common good. Sometimes, the pairings were more surreal than sensible—Bing Crosby doing “Little Drummer Boy” with David Bowie, or Andy Williams chatting it up with the Cosby kids—but that was the fun of it. Christmas, as Pee-wee notes in the special, is a time to think of others and what they want. For celebrities, if that means painting your teeth green for a gag, as Annette Funicello does, so be it. If Cher can get super-stoked about Conky and the secret word while wearing a bodysuit and pantyhose, great. That kind of ridiculousness makes the audience’s holiday a little brighter. It’s Hollywood’s gift to the viewing public.
It’s a testament to the Pee-wee’s Playhouse Christmas Special that all these years later, it’s still totally weird. It takes the most tried and true holiday punchlines—fruitcake, yellow snow, people falling down when they ice skate, etc.—and, rather than modernizing them, revels in their stodginess. Old knee-slappers like unexpectedly going off a ski jump worked 50 years ago, they worked in 1988 when the special aired, and they work today. Why they work is anyone’s guess—physical humor and the threat of real harm, maybe—but they still do, so why try to reinvent the holiday gag wheel?
Pee-wee creator Paul Reubens and company did manage to shake things up a bit, though. The special’s roster of guests not only seems like a throwback to the televised holiday hullabaloos of the ’50s, ’60s, and ’70s, but also reads like a who’s-who of gay icons of the late ’80s. Cher, Oprah Winfrey, Dinah Shore, Joan Rivers, Grace Jones, Zsa Zsa Gabor, K.D. Lang, Charo, and Little Richard all stop by. A handsome choir of actors dressed as Marines cart around a singing Pee-wee in the opening, and a couple of hunky, shirtless construction workers work on Herman’s fruitcake-clad annex later in the episode.