My Lifelong Journey to Find Pee-wee Herman

My first attempt to meet him turned out to be a cover story for my parents' messy split. Thirty years later, I decided to find Pee-wee on my own terms.

Three years ago, Paul Reubens – a.k.a Pee-wee Herman, a.k.a. my lifelong hero – read this Narratively story of mine from August 2020 and initiated what has become one of my life’s joys: our little friendship. 

“I just read your story about meeting me in New York at Comic Con,” Paul wrote. “It was so lovely; I seriously got choked up reading it. I want you to know that I remember just about every detail of what you said to me— Especially about the taped up VHS box and me telling you to tell your dad thank you. I really appreciate Your story, and you -- it has real meaning and impact for me. I wish you love and luck -- and sorry it took so darn long for us to finally meet! 😀”

Since then, Paul and I have exchanged encouraging notes and emoji streams. With each one, I whispered to myself, “my friend Pee-wee.” And it blew my freaking mind. 

Sharing what Pee-wee Herman meant to me in my Narratively story was all I could’ve wanted. That Paul gave me even more is a testament to the kindness that I hope, just after hilariousness, will be his legend. 

Last May, when I was eight months pregnant and going through a difficult time, I made a Pee-wee’s Playhouse-themed nursery to surround myself with positivity. And then, there he was: Paul shared my nursery photos and congratulations across his social media feeds, and thousands of uplifting comments poured in from fans across the world. 

In a video message, Paul talked about parenthood being my next Big Adventure. And again, he brought up my Narratively story, republished in full below, calling it “a valentine.” Amid the tremendous sadness of his passing this week, I am so grateful for what that valentine made possible. By doing what Paul taught me to — being my weirdo writer self — I finally found Pee-wee. And I will miss him very much.

–Angelina Drake

Illustration by Siah Files | Edited by Lilly Dancyger

I can’t remember a time before Pee-wee Herman. This is true chronologically, as Paul Reubens began appearing exclusively as his most iconic character years before I was born, but Pee-wee has also been a constant in my family story. My first trip to meet him was a cover for my parents’ separation and the harsh means through which it was achieved. As a result, I experienced what should’ve been the defining traumatic event of my early life as something else entirely: a big adventure.

In the mid-1980s, my mom and dad forged their identities in the punk music scene at the edges of the University of Florida. Pee-wee’s Playhouse had an in-your-face energy and subversive visual reinterpretation of old-school children’s television that made it required watching among their friends.

“You have to understand,” my dad explains every time we pass the apartment where my godmother, Mom’s first bandmate, used to live. “Very few people had cable back then. CBS didn’t have a local affiliate, but Sharon had a 12-inch TV with a wire hanger antenna that caught the Jacksonville signal. When I met your mom, we all went over there on Saturday mornings to get stoned, eat grits and watch Playhouse.”

In the rush to prepare for parenthood a few years later, my folks thought it convenient that they were already watching a children’s show. My dad made a ritual of recording Pee-wee’s Playhouse every weekend for the first three years of my life. He’d sit within arm’s reach of the VCR so that he could modulate the record button, saving me from the influence of commercial breaks. On the cardboard sleeves, he scrawled his own summaries of the episodes in theatrical cursive: “Pee-wee Has a Cold and Gets Real Cranky!” or “Whomever Will Pee-wee Bring to the Luau (to Eat the Pupu Platter!)?”

We played those VHS mixtapes and a copy of the feature-length Pee-wee’s Big Adventure from the bargain bin at Pick ’n Save nonstop at home. Every time the phone rang, the three of us zigzagged around the house yelling, “I’ll get it! I’ll get it!” like outfielders under a fly ball. On Playhouse, this was how Pee-wee answered his Picture Phone. The yelling was ironic, as he was the only nonstationary being at home.

My mom’s favorite character from the show, she said, was “a tie between Cowboy Curtis and Chairry.” The concept was new to me, that you could love two choices just as much.

Chairry was a plush, teal-colored recliner with long eyelashes, and was the centerpiece of the Playhouse. Trusty and comforting, she was always there to soften Pee-wee’s landing when he flew out of an adventure inside Magic Screen.

“Oh, where would I be without you, Chairry?!”

“On the floor, Pee-wee.”

Thirty years later, the call-and-response routines that Playhouse set up are still automatic for me. You know what to do when someone says today’s secret word? Scream! Real! Loud! Miss Yvonne? The most beautiful woman in Puppetland! Going door-to-door with an incredible offer? Aaah! Salesman!

My dad created similar cues during a long drive west in 1991, just after preschool. The two of us were going to see Pee-wee, he said. It would be worth the wait.