Who is the coolest character from 'Pee-wee's Playhouse'?


Image 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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Comments (40 total) Add your comment
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  • Destro the Scottish Love Machine

    where is Reba the mail lady?

    • Lindsay

      I loved Reba the Mail Lady! Agreed. She was sassy.

      • BJG

        I liked Reba bcause she was kind of sensible which made here odd in the Playhouse. I think I liked Penny most of all, though, because her imagination would just go on forever.

  • Chris

    Randy, because he was a smoker. Which is kind of ironic, since he was made out of wood.

    • Karate Pants

      Randy was SUCH a d!ick.

      • Chris

        Seriously, I liked Conky the best. Secret Word!

  • Karate Pants

    The show would be without Pee Wee, obviously…but I gotta give it Jambi.

    • jj

      Funny how I hated this show when I had to watch it while babysitting my 8 year old cousin and find it fabulously craptastic in its campiness as an adult. Just saw the broadway show on HBO the other night and was RIVETED. Peewee forever!

  • Kelly

    Cowboy Curtis hands down. Jambi a close second

    • tiacheryl

      I’ve had a crush on Laurence Fishburne ever since his Cowboy Curtis days, weird Jheri curl and all.

  • Shameless

    Cowboy Curtis was in Apocalypse Now an junior high and grew up to be Morpheus, how cool is that?

    • time4bedlam

      but the King of Cartoons was Blacula, how cool was that!

      • kennedyDC

        Really? I did not know that. How cool!

  • Bobby’s Robot

    Tito the lifeguard

  • tracy bluth

    Chairy was always my favorite, but I think Cowboy Curtis is the coolest (you can’t really argue with Shameless’ logic). Although Miss Yvonne also plays Charlie’s mom on It’s Always Sunny, so that earns her some cool points in my book.

  • MailPlease

    Hey, what about Reba The Mali Lady (S. Epatha Merkerson)?!

  • AA

    I immediately thought of Pterri when I saw the headline. I always had a soft spot for him. Penny (and her eyes) was pretty good too.

  • JPX

    It’s all about Konky!

  • Butters

    mecca-lecka-hi-mecca-johnny-ho. mecca-lecka-hi-mecca-hiny-ho!

    • MikeB

      Love it!!!!!


    How could you forget Conky? He gave out the secret word, after all.

    I also liked Pterri.

    • Caracticus

      I wanted to vote for Conky and he wasn’t listed. Consider this a write-in (I voted for Jambi as my second choice)

  • Anne

    Twenty-plus years later I still get cracked up thinking of, “Here a chick-chick and there a chick-chick, and there a chick-chick, and there a chick-chick, and there a chick-chick, and — AAAHHHHHHH! TOO MANY CHICK-CHICKS!!!!!!”

  • EG

    It’s “Cowboy Curtis” not “Cowboy Carl” as stated in this write-up. The show also had a Captain Carl played by Phil Hartman.

  • maxwell19596

    Having recently purchased Season 1, and 2 DVD set I am happily reliving this show every day. I used to watch it every Saturday morning way back in the 80’s, I would video tape it, and watch it again with my girlfriend who always was asleep when it came on ( I think it was aired at 10am) Conky was certainly one of the coolest how many kids have a robot, soon maybe, but not yet. I am thrilled that the Pee Wee Broadway show was a hit, and now Paul is writing a new movie! Yes! BTW today’s secret word is “Cool” so anytime you read the secret word on this page scream real loud! now how cool (aaaahhhh) is that!

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