A look back at 6 surprising guest stars… including Oprah

Paul Reubens’s delightfully demented alter ego Pee-wee Herman entertained a generation of kids during the five-season, Emmy-winning run of Pee-wee’s Playhouse airing on CBS from 1986 to 1990.

With the shocking news Monday of Reubens’s death at age 70, following a private bout of cancer, we wanted to look back at the seminal Saturday morning show, which had such a huge impact on pop culture that some of Hollywood’s biggest names lined up as guest stars.

If you are looking for episodes to watch in tribute — the show is streaming on Hoopla and is available to rent/buy from Prime Video and Google Play, here are a half-dozen drop-ins by notable celebrities.

1. Phil Hartman

Paul Reubens and Phil Hartman (Screengrab: Pee-wee Pictures)

Paul Reubens and Phil Hartman on Pee-wee’s Playhouse. (Screengrab: Pee-wee Pictures)

“The Restaurant” (Season 1, Episode 7)
Friends with Reubens since their days in the storied Los Angeles comedy group the Groundlings, Hartman (who also co-wrote Tim Burton’s Pee-wee’s Big Adventure) appeared as the cantankerous mariner Captain Carl for several episodes during Playhouse’s first season. In this particular voyage, he dropped by Pee-wee’s recently opened restaurant, but got salty when he learned that the only item on the menu was PB&J.

2. Laurence Fishburne

Laurence Fishburne and Paul

Laurence Fishburne and Paul “Pee-wee” Reubens on Pee-wee’s Playhouse. (Screengrab: Pee-wee Pictures)

“The Cowboy and the Countess” (Season 1, Episode 10)
Fishburne’s stylish cowpoke was a favorite visitor around the Playhouse, and one of Pee-wee’s closest human confidants. They were such good friends that Pee-wee even did the unthinkable in this episode and let Curtis have dibs on his weekly Jambi-granted wish. The lucky dude also gets to go on a date with Miss Yvonne, an experience that probably gave him plenty of great campfire stories.

Speaking to Yahoo for our Role Recall series, Fishburne recalled his time on set. “When I think about Pee-wee’s Playhouse I think about what it might have been like to work on the Batman television series with Adam West, because it was … campy and colorful and sort of for kids and grownups, too. That’s my attempt at working in a Western.”

(Fun fact: While working on Playhouse, Fishburne struck up a friendship with a USC film student who was moonlighting as a security guard on the set. He told Fishburne he was working on a script and wanted the actor to star in it. The student turned out to be John Singleton and he did cast Fishburne in the role of Furious Styles in what became the Oscar-nominated sensation Boyz n the Hood.)

3. Natasha Lyonne

Natasha Lyonne (Screengrab: Pee-wee Pictures)

Natasha Lyonne on Pee-wee’s Playhouse. (Screengrab: Pee-wee Pictures)

“Party” (Season 1, Episode 13)
The future star of Orange Is the New Black, Russian Doll and Poker Face was one of three members of the Season 1 Playhouse Gang, a group of kids that Pee-wee invites over for fun and games. In the Season 1 finale, they’re among the guests at a big Playhouse party that’s a celebration of all things Pee-wee.

Upon news of his death, Lyonne expressed her love and gratitude for Reubens for her Hollywood break. “Thank you for my career and your forever friendship,” she wrote.

4. S. Epatha Merkerson

S. Epatha Merkeson (Screengrab: Pee-wee Pictures)

S. Epatha Merkeson on Pee-wee’s Playhouse. (Screengrab: Pee-wee Pictures)

“Reba Eats and Pterri Runs” (Season 3, Episode 1)
Before she laid down the Law & Order, the Emmy-winning actress made her screen debut as Playhouse’s dependable mail-deliverer.

Neither snow nor rain nor heat nor gloom of night keeps away Pee-wee’s faithful letter carrier Reba from her appointed rounds. When Season 3 rolled around, he decided to get to know her a little better, inviting her for breakfast after she swings by on her day off to pick up a letter bound for his pen pal. In an unwelcome surprise, though, the breakfast table turns out to be filled with imaginary food. You gotta stock the Playhouse fridge with more ingredients, dude!

5. Oprah Winfrey

Oprah Winfrey (Screengrab: Pee-wee Pictures)

Oprah Winfrey on Pee-wee’s Playhouse. (Screengrab: Pee-wee Pictures)

“Pee-wee’s Playhouse Christmas Special” (Season 3, Episode 3)
Although a host of celebrities attended Pee-wee’s Christmas shindig — including former Mouseketeer Annette Funicello, superstar singer Little Richard and music/fashion icon Cher — Oprah’s literally phoned-in cameo impresses the most. Her dead-on impression of Pee-wee’s trademark laugh is one more reason why she’s the television royalty.

6. Jimmy Smits

Jimmy Smits and Paul Reubens (Screengrab: Pee-wee Pictures)

Jimmy Smits and Paul Reubens on Pee-wee’s Playhouse. (Screengrab: Pee-wee Pictures)

“Conky’s Breakdown” (Season 5, Episode 1)
When Conky goes on the fritz, Smits (taking a timeout from his breakthrough role on L.A. Law), comes to the rescue as an officially licensed Conky repairman. He also trades vaguely PG-13 rated double entendres with the always-risque Miss Yvonne. Good luck explaining to your kids why she’s smiling when Smits says that qualified repairmen always “have the right tools and know how to use them.”

All five seasons of Pee-wee’s Playhouse are currently streaming on Hoopla and are available to rent/buy from Prime Video and Google Play. Season 1 is also streaming on Apple TV+.

Editor’s note: a version of this story originally ran on March 18, 2016.

Leave a Comment