In 1988, a holiday special in the longstanding tradition of celebrity-hosted variety shows was aired on CBS. Christmas at Pee Wee’s Playhouse was produced as an offshoot of the Pee-wee’s Playhouse series that to this day still has a huge cult following.
The schtick of Pee-wee Herman and the productions creator Paul Reubens mounted around the character could be described as comic, campy, childlike, quirky, and naïve. Pee-wee is surrounded in his Playhouse by kooky inventions and decorations, and lives a pixie-like existence, like Pippi Longstocking or Peter Pan. Though he constantly appears in a grey plaid suit and red bowtie, the character emanates androgyny with rouge and red lips atop pale makeup, and Leave It to Beaver black hair. Reubens has credited the lively fast-paced dynamic of Pee-wee’s Playhouse as the reason it resonates with kids (of all ages).
That great balance does not minimize the transcendent jokes, the queer overtones and undertones, and the physical and facial humor, all of which has allowed Pee-wee’s Playhouse and Pee-wee to stand the test of time despite the personal trials of Reubens that curtailed his career. And of course there is the classic Christmas at Pee Wee’s Playhouse which is a delight of holiday INSANITY.
Christmas at Pee Wee’s Playhouse starts with the most fabulous, over the top musical intro—with the UCLA Men’s Chorus pretending to be a military choir, gay inside joke number one—we get tantalized by a who’s who cast of WTF guest stars (Magic Johnson) and guest stars that make perfectly campy holiday-special sense (Dinah Shore, Charo who sings “Feliz Navidad” as Pee-wee tries to hit a piñata).
Then we see Pee-wee in the Playhouse telling his robot Conky his Christmas wish-list, which prints out miles long.
The wacko cast begins to make entrances one by one, each presenting Pee-wee with a fruitcake. The fruitcake joke continues throughout the special, each time followed by a sad trombone sound, toward an eyebrow-raising end punchline in which all the bricks of fruitcake are being used for a new playhouse wing, built by two chesty construction workers!
King of Cartoons is played by William Marshall, famous for the title role in the Blacula film franchise. He comes in to change the TV channel to play a holiday cartoon. Zsa Zsa Gabor plays Princess Zsa Zsa, and tells Pee-wee she loves him. “Then why don’t you marry me?” he asks back, using one of Pee-wee’s trademark phrases.
Playhouse regular Ms. Yvonne spins a mistletoe gag in a suggestive manner. When all the talking gadgets and furniture (like Chairy) beg her for a mistletoe kiss she responds: “Don’t worry. There’s enough of me for everyone!”
Another regular, Reba the Mail Lady, delivers Grace Jones in a crate to Pee-wee. In a jaw-dropping metallic futuristic getup, the gorgeous diva sings Little Drummer Boy.
Frankie Avalon and Annette Funicello (wearing a 1950s Mouseketeer-era sweater and skirt) are enlisted by Pee-wee to make X-mas cards (wholesome and educational). When they laugh at their own cornball jokes, Pee-wee snaps his fingers and scolds, “All right, I’m gonna have to separate you two,” and orders them to each make 500 cards. Sad trombone.
Cher! She appears looking for the day’s secret word—it’s year, and everybody screams at its mention. Pee-wee recites a poem in her honor.
“That was Cher! Cher was right over there! In the same room as my chair! I hope I didn’t stare! Oh well! I don’t care!”
Joan Rivers appears in a Hollywood Squares joke wearing an angel wing angora “Merry Christmas” sweater.
Pee-wee goes out in the snow, makes a yellow snow joke, and proceeds to go over the top again by teaching Little Richard how to ice skate.
The casting pendulum swings after that, with k.d. lang singing “Jingle Bell Rock.” According to IMDB trivia, k.d. lang’s appearance was the longest to shoot, half a day (veteran Cher took 25 minutes).
Keep reading, because Dinah Shore calls Pee-wee up to sing him “The 12 Days of Christmas.” An incoming call from Oprah with a holiday wish puts Dinah on hold. After speaking with Oprah he resumes listening to Dinah, then quickly puts a mannequin with a Pee-wee mask in his place and leaves the phone booth.
OMG, we are then entertained by Sofia Vergara-predecessor Charo, Mrs. Rene teaching about Hanukkah also singing “The Dradel [sic] Song,” a visit by Shakespearean actor and series regular Laurence Fishburne as Cowboy Curtis, and the Del Rubio Triplettes who had a significant cult following in their own right. Santa Claus shows up, informs Pee-wee his greedy Christmas list has depleted the world’s toy supply, and guilts him into giving back all the gifts so that they can be fairly distributed among children. In Pee-wee’s sincerely earnest send-off to the television viewing audience, he says, “My wish is that there’s peace on Earth, and that everybody has the very Merriest of Christmases and,” here he rolls his lips to deliver his last thoughts in that tooty Ethel Merman timbre, “a Happy New YEAR!” Everybody screams with delight at the word of the day!