Raised in the Tennessee mountains, Wayne White started his career as a cartoonist in NYC. He quickly found success as one of the creators of the Pee-wee's Playhouse TV show which soon led to more work designing some of the most arresting and iconic images in pop culture. Recently his word paintings featuring pithy and and often sarcastic text statements finely crafted onto vintage landscape paintings have made him a darling of the fine art world. The movie chronicles the vaulted highs and crushing lows of an artist struggling to find peace and balance between his professional work and his personal art. This is especially complicated for a man who struggles with the virtues he most often mocks in his art...Vanity, ego and fame.

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?