Pee-wee's Playhouse Christmas Special is a Christmas television special based on the American Saturday-morning children's program Pee-wee's Playhouse. The special is a variety show that features a number of celebrities of the time as well as several musical numbers, educational segments, and segments commonly found in the show: a secret word ("year"), connect the dots with the Magic Screen, a visit from the King of Cartoons, a clay animation Penny cartoon, etc.
It is Christmas Eve of 1988 and Pee-wee, with the help of his robot pal Conky 2000, has spent a great deal of time creating an abnormally large Christmas list for Santa. Only after Miss Yvonne stops by the Playhouse (wearing a new hairdo and a beautiful Christmas dress) to drop off a Christmas fruitcake does Pee-wee realize that he hasn't yet decorated for the holidays. Thankfully, Pee-wee's genie Jambi grants his wish that the playhouse be magically decorated, though the man-child decides to tack on an extra wish that is going to be granted later.
As the special continues, various characters from the show as well as various celebrity guest stars stop by to visit Pee-wee - for instance, Cowntess the Cow arrives with pal Zsa Zsa Gabor, the Magic Screen's cousin Magic Johnson makes an appearance, and Jewish neighbor Mrs. Rene gives a short lesson on Hanukkah and the dreidel.
At the end of the special, Santa arrives and informs Pee-wee that since his list was so large, there wasn't room on the sleigh for any presents for the other kids of the world. Although he initially acts selfishly and conceitedly (much to his friends' and viewers' displeasure), Pee-wee decides to give up all of his presents so all the rest of the children on Earth and their families and friends can have a merry Christmas - after all, "Christmas is the time when we should be thinking of what we can do for others." Pee-wee then uses his extra wish from Jambi to wish for peace on Earth and that everyone will have a Merry Christmas and a Happy New "Year".
- Pee-wee is often seen giving odd or humorous gifts to his friends: Miss Yvonne gets a bottle of "Eau de Pee-wee" perfume that smells like Pee-wee, Reba the Mail Lady gets a set of press-on toenails, and Cowntess the Cow gets a cowbell that plays "We Wish You a Merry Christmas".
- Pee-wee keeps receiving fruitcakes as Christmas gifts - Miss Yvonne, Reba the Mail Lady, the King of Cartoons, Cowboy Curtis, the food in the refrigerator, Mrs. Rene, Randy and Charo are all seen giving Pee-wee a fruitcake. Eventually, we learn that Pee-wee is having a new wing added to the playhouse made completely out of fruitcake when he opens a door to deliver fruitcakes to three shirtless male construction workers busy working on the new wing.
- Annette Funicello and Frankie Avalon give a lesson on making homemade Christmas cards with paint, stencils and potatoes. Pee-wee holds Frankie and Annette captive until they made 1000 cards and envelopes. Pee-wee stops by to check on their progress several times during the special, and offers them bread and water when they complain that they are hungry and thirsty.
- Dinah Shore calls Pee-wee on the Picturephone to sing a song to him - "The Twelve Days of Christmas". Pee-wee tires of the song and sneaks out of the Picturephone booth. Several times during the special, Pee-wee passes by the booth to hear Dinah still singing the song past the original twelve days ("On the five-hundredth day of Christmas...")
- Annette Funicello
- Frankie Avalon
- Grace Jones (sings "Little Drummer Boy")
- K.D. lang (sings "Jingle Bell Rock")
- Dinah Shore (sings "The Twelve Days of Christmas")
- Little Richard
- Magic Johnson
- Zsa Zsa Gabor
- Del Rubio Triplets (sing "Winter Wonderland")
- Whoopi Goldberg
- Oprah Winfrey
- Joan Rivers
- Charo (sings "Feliz Navidad")
- Miss Yvonne wears a red, green, and white Christmas-themed dress in the special. This dress also appeared in the Pee-wee's Playhouse series in the episode "Miss Yvonne's Visit." Lynne Marie Stewart, the actress who played Yvonne, stated in the actors' DVD commentary that she still owns the dress.
- The Del Rubio Triplets would again appear on Pee-wee's Playhouse in the episode, "Dr. Pee-Wee and the Del Rubios." In that episode, they perform "These Boots Are Made For Walking".
This special was released on VHS and Laserdisc by Hi-Top Video in 1989, and again by MGM Home Entertainment in 1996. The special made its DVD debut in 2004, when it was released on the format by Image Entertainment. It was also included in Image Entertainment's Pee-Wee's Playhouse: The Complete Series set, and made its high-definition debut on the Blu-ray set of the same name, released by Shout! Factory on October 21, 2014. Shout! Factory would later give the special its own individual Blu-ray release on October 6, 2015.