The original adult-oriented version of what would eventually become an award-winning children's classic. This version of the show features Pee-wee's playhouse and many of the characters of the later series, but with irreverent overtones and jokes including 'mirror shoes' and others.

Pee-wee Herman and pals are celebrating Christmas in the Playhouse in their own creative ways: Pee-wee makes a list for Santa Claus 1.5 miles long, teaches Little Richard how to ice skate, goes for a sleigh ride with Magic Johnson, enslaves Frankie Avalon and Annette Funicello into making Christmas cards, receives a long phone call from Dinah Shore, even has more musical fun with k.d. lang, the Del Rubio Triplettes and Charo! Finally, Big Red arrives and announces that Pee-wee's Christmas list was so big, he didn't have enough presents for all the children of the world. Will Pee-wee follow his own advice and help others?