It features many characters that would go on to appear in Playhouse, including Captain Carl, Jambi the Genie, Miss Yvonne, Pterri the Pterodactyl, and Clocky.

While enjoying continuous popularity with the show, Reubens teamed with young director Tim Burton in 1985 to make the comedy film Pee-wee's Big Adventure.

Production began in New York City in the summer of 1986 in a converted loft on Broadway, which one of the show's writers, George McGrath, described as a "sweatshop".

[11] The creative design of the show was concocted by a troupe of artists including Wayne White, Gary Panter, Craig Bartlett, Nick Park, Richard Goleszowski, Gregory Harrison, Ric Heitzman, and Phil Trumbo.

The first day of production, right as Panter began reading the scripts to find out where everything would be situated, set workers hurriedly asked him, "Where's the plans?

The house is filled with toys, gadgets, talking furniture and appliances (such as Magic Screen and Chairry), puppet characters (such as Conky the Robot and Pterri the baby Pteranodon), and Jambi (John Paragon), a disembodied genie's head who lives in a jeweled box.

[8] Each episode features specially written soundtrack music by rock and pop musicians such as Mark Mothersbaugh (Devo), Todd Rundgren, Mitchell Froom, and The Residents.

The show's theme song performance is credited to "Ellen Shaw", though in her autobiography, Cyndi Lauper admits to being the actual singer.

Many now-well-known TV and film actors appeared on the show, including Sandra Bernhard, Laurence Fishburne, Phil Hartman, Natasha Lyonne, S. Epatha Merkerson, Jimmy Smits, and Lynne Stewart.

[28] The Christmas special episode, "Pee-wee's Playhouse Christmas Special", aired between seasons 2 and 3 and included the regular cast, along with appearances by Annette Funicello, Frankie Avalon, Magic Johnson, Dinah Shore, Joan Rivers, Zsa Zsa Gabor, Oprah Winfrey, Whoopi Goldberg, Little Richard, Cher, Charo, k.d.

As soon as it first aired, Pee-wee's Playhouse fascinated media theorists and commentators, many of whom championed the show as a postmodernist hodgepodge of characters and situations that appeared to thumb its nose at the racist and sexist presumptions of dominant culture.

[35] O'Connor lauded the show's mixed-media format and commented that the Saturday morning kids' programming of "low-cost, dreary and occasionally questionable cartoons will never be the same" after Pee-wee.

[35] Of Pee-wee, O'Connor said, "He whips up a tightly contained world in which anything is possible as long as it doesn't hurt anyone", and "He's sweetly looney and unpredictable, gentle yet always tip-toeing on the edge of devastating absurdity.

[36] Captain Kangaroo's Bob Keeshan hailed the show's "awesome production values", adding, "with the possible exception of the Muppets, you can't find such creativity anywhere on TV.

[5] On November 1, 2011, in commemoration of the 25th anniversary of the show, a book by Caseen Gaines called Inside Pee-wee's Playhouse: The Untold, Unauthorized, and Unpredictable Story of a Pop Phenomenon, was released by ECW Press.

[39] In the wake of Reubens' death from cancer in 2023, John Jurgensen of The Wall Street Journal wrote: "Pee-wee Herman wasn't originally meant for kids.

With his wild remix of the kids' shows that he grew up with as a baby boomer, Reubens put a stamp on Generation X.⁠"[40] Image Entertainment first released all 45 episodes of Pee-wee's Playhouse on DVD in 2004.