HBO’s latest docu-series, “Pee-wee as Himself,” chronicles the life and times of actor and comedian Paul Reubens, best known for originating the character of Pee-wee Herman in “The Pee-wee Herman Play Show.”
The upcoming two-part documentary, which will be available to stream on HBO/Max from 8:00pm ET on Friday, May 23, looks back on the highs and lows of the late actor’s life, including his work on “Pee-wee’s Playhouse,” a children’s musical comedy series starring Reubens as Pee-wee Herman that aired as part of CBS’s Saturday morning lineup from 1986 to 1990.
Amongst the many actors who appeared on “Pee-wee’s Playhouse” during its four-year run on CBS, many went on to have illustrious careers in Hollywood, including stars like Laurence Fishburne and Natasha Lyonne.
Laurence Fishburne Then & Now
CBS/20th Century StudiosShortly after appearing in “The Color Purple” in 1985, Laurence Fishburne joined the cast of “Pee-wee’s Playhouse” in the role of Cowboy Curtis. The prototypical 1950s cowboy was a close-friend of Pee-wee’s on the show until Fishburne left the production in Season 3 to film “A Nightmare on Elm Street 3.”
Since his time on “Pee-wee’s Playhouse,” Fishburne has become an Oscar-winning actor thanks to his role in the 1993 film “What’s Love Got to Do With It.” Now 63, the actor made a name for himself in the science-fiction community, starring in a string of successful sci-fi franchises including the Marvel Cinematic Universe, “John Wick” and, most prominently, “The Matrix.”
In 2025 Fishburne is still acting in films, like “The Amateur” with Rami Malek, and on TV, in Season 4 of “The Witcher” on Netflix.
S. Epatha Merkerson Then & Now
CBS/NBCFrom humble beginnings as Reba the Mail Lady on “Pee-wee’s Playhouse,” S. Epatha Merkerson went on to win Emmys, Golden Globes, and Obie Awards for her acting performances in film and TV.
After playing Puppetland’s mail delivery woman on “Playhouse,” Merkerson made a name for herself when she joined the cast of NBC’s “Law & Order” as Lieutenant Anita Van Buren in 1993. Merkerson remained with the show until 2010, starring in a total of 388 episodes.
In 2025, Merkerson continues her primetime television career in the role of Sharon Goodwin in NBC’s medical drama “Chicago Med.”
Sandra Bernhard Then & Now
CBS/Apple TVStand-up comedian Sandra Bernhard only appeared in one episode of “Pee-wee’s Playhouse,” in the role of Rhonda the Picturephone Operator, before going on to join the cast of ABC sitcom “Roseanne.” In the role of Nancy Bartlett Thomas, Bernhard stayed on the cast from 1991 until its conclusion in 1997.
More recently, Bernhard has starred in projects like Ryan Murphy’s “Pose” from 2018 to 2021, and in the Apple TV thriller “Severance” in 2025. Beyond her acting career, Bernhard has also been named one of Comedy Central’s Top 100 Greatest Stand-Up Comic’s of All Time since her time on “Pee-wee’s Playhouse.”
Natasha Lyonne Then & Now
CBS/PeacockBefore she was an Emmy Award-winning actress, Natasha Lyonne appeared on the first season of “Pee-wee’s Playhouse” in 1986 as Opal, a member of The Playhouse Gang. Lyonne, along with her Playhouse Gang co-stars Shaun Weiss and Diane Yang Kirk, were later fired from the show due to destructive behavior on set.
The actress would go on to star in films like “But I’m A Cheerleader,” “Slums of Beverly Hills” and “American Pie” in the late 1990s. In the 2010s Lyonne took to television, starring in series like “Orange is the New Black” and “Russian Doll.” In 2025, the 46-year-old actress is making her MCU debut in “Fantastic Four: First Steps,” and continuing to appear in the Peacock thriller “Poker Face.”
Diane Yang Kirk Then & Now
CBS/SHOWTIMEUnlike her The Playhouse Gang co-star, Diane Yang Kirk, who played Cher on “Pee-wee’s Playhouse,” hasn’t seen the same success in acting, but that hasn’t kept her from appearing as background and side characters in a plethora of projects, ranging for “NCIS: Los Angeles” and “Criminal Minds: Beyond Borders,” to “Grey’s Anatomy” and “How I Met Your Father.”
Most recently, Kirk appeared in the role of Mary in the Netflix series “Monsters: The Lyle and Erik Menendez Story” in 2024.
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’Pee-wee’s Playhouse’ Cast Then & Now