Credit: Photofest

There’s simply no other way to put it: Pee-wee’s Playhouse was a totally bizarre television show, especially when you consider that it was made for children. An effeminate, over-sized man-child ran around like a loon in a giant, surreal house that featured a rotating cast of characters and puppets even wackier than him? Yes, surely, that was Pee-wee’s Playhouse, indeed.

But that description actually brings us to the important thing about Pee-wee’s Playhouse, the thing that made the show so darn addictive and special: its cast of insane, memorable characters, all of which fall into two camps. The humans, led by master-of-ceremonies Pee-wee, of course, and pretty-pretty Miss Yvonne and aww-shucks-ish Cowboy Carl. And then there were all the puppets and object characters, ranging from Clockey, the talking clock, to Pterri, the sweet pterodactyl. Everyone had a distinct and important role on the show. But who was the coolest? Well, the obvious answer would be, of course, Pee-wee. But maybe it’s not quite that easy? We’ve broken down a handful of the faves (sorry if yours didn’t make the list — there are literally dozens on the show!) below:

Pee-wee Herman

Hobbies: Being loony, talking to puppets, making lots of weird faces.

Why He Is Cool: Because he was the ringleader of it all, and because this was one of his many catchphrases: “I know you are, but what am I?”


Hobbies: Telling time.

Why He Is Cool: Because — duh — he’s a talking clock.


Hobbies: Hugging Pee-wee.

Why She Is Cool: Because she’s so dang sweet — you can’t really not love Chairry.

Cowboy Curtis

Hobbies: Talking slow, flirting with Miss Yvonne.

Why He Is Cool: Because he was played by Laurence Fishburne.


Hobbies: Granting wishes.

Why He Is Cool: Because of that kick-a– turban he wore.

Miss Yvonne

Hobbies: Obsessing over her beauty, wearing a bouffant hairdo, being “the most beautiful woman in Puppetland.”

Why She Is Cool: Because of the insane hair.


Hobbies: Getting picked on, being scared and overly sensitive.

Why He Is Cool: Because he can fly. Sort of.


Hobbies: Speaking with a French accent, helping Pee-wee with questions about language, geography, and history.

Why He Is Cool: Because he had all the answers.

King of Cartoons

Hobbies: Playing old cartoons.

Why He Is Cool: Because what kid doesn’t love someone who plays cartoons for them?

Now, tell us who your fave is in the poll here:

Was your favorite character not on the list? Let us know below in the comments, if not!

Tanner on Twitter: @EWTanStransky

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