The special begins in a snowy landscape, as we pan to the title card. We then move on to the Playhouse. Inside, the UCLA Men's Glee Club, as a Marine Choir, sings the introduction. Pee-Wee welcomes the viewer to the special, and introduces the cast and guest stars. As Pee-wee finishes the song, the choir lifts him above their heads.
Next, while Pee-Wee goes over his really, really long list of gifts, he lists a yo-yo, but Conky points out that he already has a yo-yo, which Pee-wee finds and plays with, but ends up breaking the camera. Pee-wee concludes his list with a really long closing, and a really long postscript. While Conky goes crazy rapidly printing it out, Pee-wee brings in a large envelope, when Miss Yvonne visits, with her hair styled like a Christmas Tree. She gives Pee-wee a present - a fruitcake! Then Pee-wee gives her a present - Eau de Pee-wee Perfume. As Pee-wee goes to put his first fruitcake in the fridge, he sees the food celebrating Christmas. The freezer food fish out another present for Pee-wee - a teeny-tiny fruitcake.
Then, someone calls on the Picutrephone. Pee-wee receives a call from Whoopi Goldberg, who asks him if he can be cast in his Christmas special, but Pee-wee has already booked too many stars as it is, even in next year's Christmas special. He hopes he'd be able to see Whoopi in about two years from now. After saying goodbye, Magic Screen invites Pee-wee to play Connect the Christmas Dots with her. The dots form a sleigh. Magic Johnson, Magic Screen's cousin, joins in the ride with him.
Back in the Playhouse, Pee-wee realizes he forgot about the decorations. After he says he wishes he hadn't been selfish, Jambi comes out and Pee-wee tells him his problem and lets him accept an extra wish to use for later. After chanting the magic words, Jambi magically decorates the Playhouse festively. Then, Reba enters the house with a bag of Christmas cards, along with another present for Pee-wee - another fruitcake! Pee-wee then gives Reba his envelope and a present for her: press-on toenails. It reminds Reba that she has a great big package delivered to the house. Grace Jones comes out of the box. When she sees Pee-wee, she says "You're not the President. You're Pee-wee Herman." Reba reads the label that the package was supposed to be delivered to the White House, not the Playhouse. However, Grace decides to perform a musical number right here, right now, singing "Little Drummer Boy".
After a break, Pee-wee shows us his next guests - Frankie Avalon and Annette Funicello, making Christmas cards. Pee-wee commands them to make 500 of them before sundown. Next, Pee-wee sees Cher decorating Conky like a Christmas tree. It reminds Pee-wee that he forgot to know what today's secret word is. So, Conky displays today's secret word - year. After he explains the secret word rules, he asks Cher how she likes Christmas so far. Cher: "Christmas is my favorite time of year". Everyone screams. After Cher leaves, the King of Cartoons arrives. He has a present for Pee-wee - two more fruitcakes! As the King turns on the TV, Joan Rivers appears, playing Hollywood Squares. Pee-Wee, King, and Annette wish Joan a Merry Christmas, before they watch a Christmas-themed cartoon.
After that, Billy Baloney decides to sing on the Christmas special, when Pee-wee reminds him maybe next year. Then outside, Mr. Kite announces that it's snowing. Pee-wee, reacting excitedly, puts on his winter outfit, letting Frankie and Annette continue working with cards. Out in the snow, Pee-wee makes a snow angel and makes mystery tracks. When Cowboy Curtis comes by and wonders who made those footprints, Pee-wee surprised him, saying he made his mystery tracks. Then they hear the Del Rubio Triplets singing "Winter Wonderland".
After that, Pee-wee and Curtis build a snowman, which talks, scaring them away. Later, Pee-wee meets Little Richard at the skating pond. While Richard is having trouble skating, Pee-wee demonstrates by performing stupendous tricks. However, Richard is left surprised when he sees Pee-wee's stunt double, Hans, dressed in the same outfit he's wearing.
Back in the Playhouse, while everyone warms up with some hot chocolate, KD Land sings "Jingle Bell Rock". After that, while Pee-wee hangs stockings, Randy doesn't believe in Santa Claus. Pee-wee hangs up two giant stockings. Then Clocky announces that it's time for a Penny Cartoon. After the cartoon, Frankie and Annette are starving, so Pee-wee gives them bread and water. Next, the Cowntess gives Pee-wee a present - another fruitcake. Then Pee-wee gives the Cowntess a present - a cowbell that plays "We Wish You a Merry Christmas". Then Zsa Zsa Gabor visits Pee-wee to give him a Christmas kiss.
Then the Picturephone rings again. Dinah Shore calls him and sings him "The Twelve Days of Christmas". While she was singing, Oprah Winfrey calls from another line to wish him Merry Christmas. Not wanting to stay for the whole song, Pee-wee sneaks out of the phone and places his lookalike dummy in his place.
Then, Ricardo comes to visit and says "Feliz Navidad" and allows Pee-wee to play break the piñata, a Mexican Christmas tradition. While Pee-wee plays, Spanish singer Charo sings "Feliz Navidad". At the end, the piñata breaks open with toys and sweets. Then, Charo gives Pee-wee another pastel de fruta - fruitcake. Next, Renee comes to visit, but because she's Jewish, she celebrates Hanukkah, and gives Pee-wee eight fruitcakes, one for each night. Then they sing "The Dradel (sic) Song" with on-screen lyrics, before they play it. The dreidel spins into the Dinosaur Family's home. It breaks open with chocolate gelt. Later, Frankie and Annette are done with the cards. Pee-wee asks them to make envelopes.
After another break, Pee-wee and his friends are putting the finishing touches on the Christmas tree. Pterri puts the star on the top of the tree, and then it lights up. Then Randy unplugs the tree. Pee-wee reminds him that he forgot about the True Meaning of Christmas. Magic Screen plays a video of the Nativity of Jesus, making Randy feel touched by the True Meaning of Christmas. He gives Pee-wee a small fruitcake. When Cowboy Curtis gives him another fruitcake, Pee-wee shows his friends a new wing in the Playhouse, made entirely out of fruitcakes.
Then, while everyone sings "Pee-Wee's Christmas Medley", he hears sleigh bells, which signals the arrival of Santa Claus. Pee-wee gives him a plate of milk and cookies, but Santa has one problem: his list of so big that he didn't have enough presents for children, and he wants all his presents. Pee-wee then remembers what he said earlier: "Christmas is the time we should be thinking about what we can do for others." This makes him decide to let Santa have his presents. Santa then lets Pee-wee ride in his sleigh and help him deliver presents to the children. Pee-wee says goodbye to his friends, before Jambi asks "Hey, Pee-wee, what about that special wish?" Pee-wee decide to wish that everybody would have the merriest of Christmases and a Happy New Year! Everyone screams, and Pee-wee leaves on Santa's sleigh. The credits roll while Dinah reprises "The Twelve Days of Christmas".
- Aaron Fletcher as Santa Claus
- UCLA Men's Glee Club as Marine Choir
- Frankie Avalon
- Del Rubio Triplets
- Annette Funicello
- Zsa Zsa Gabor
- Whoppi Goldberg
- Magic Johnson
- Grace Jones
- K.D. Lang
- Little Richard
- Joan Rivers
- Dinah Shore
- Oprah Winfrey
- Hans as Pee-wee's Stunt Double
- This was a one hour special.
- This special was divided into two shows, and several parts were cut, during Fox Family airings.
- Magic Screen and Magic Johnson are cousins.
- Grace Jones sings "Little Drummer Boy."
- Pee-wee has Frankie and Annette make Christmas cards.
- Annette starts the cartoon.
- The secret word is displayed in the middle of the episode.
- Cher responds to the secret word instructions by screaming.
- Del Rubio Triplets sing "Winter Wonderland."
- k.d. lang sings "Jingle Bell Rock."
- Dinah Shore sings "12 Days (or so) of Christmas."
- Charo sings "Feliz Navidad."
- Pee Wee and Mrs. Renee sing "The Dreidel Song" with lyrics on the screen.
- Pee Wee & his friends sing "Pee-Wee's Christmas Medley":
- Jingle Bells
- It Came Upon The Midnight Clear
- Deck The Halls
- O Come All Ye Faithful
- Winter Wonderland
- Pee-Wee gets lots of Fruit Cakes.
- This special reveals that Mrs. Renee are Jewish, and so is the Dinosaur Family.
- This is the only episode where Pee-Wee doesn't ride the scooter eject at the end, and instead helps Santa deliver presents. The credits show Pee-wee and Santa riding the sleigh.
- Dinah Shore is still on the phone at the end.
- Fourth Wall (and Camera Lens) Broken: Pee-wee breaks the camera with his yo-yo. He asks Conky too put a new camera on the list.
- Out of all characters, Globey is the only character in the special without a speaking role.
- Accommodations for the show were provided by the (now-defunct) Los Angeles Registry Hotel.
- The snowman's line - "Why don't you take a picture it'll last longer!" - is said earlier in Pee-Wee's Big Adventure.
- Secret word: "year".
- Connect-the-dots: sleigh (w/ Magic Johnson).
- Snack: hot chocolate.
- First Wish: Playhouse was decorated.
- Second wish: Everyone would have a Merry Christmas and a Happy New Year.