Streaming services are teeming with celebrity documentaries, but few of those movies have inspired responses more sentimental than Pee-wee as Himself. Its overwhelming to take that in, director Matt Wolf tells The Hollywood Reporter. The scope and depth of peoples emotional reaction to the film has been surprising.

The HBO two-parter, now nominated for five Emmys (including outstanding documentary or nonfiction special), has united the many TV viewers who grew up with Paul Reubens, the Groundlings alum who subsumed his own identity through the childlike character he popularized in the 1980s. Pee-wee Hermans distinct brand of buffoonery his honking laugh, his brattiness, his oddball aesthetics felt like outsider art that somehow made its way into the Saturday morning mainstream. Wolf was one of those Pee-wee disciples. In fact, Reubens was the documentarians dream subject. What he didnt expect was a tense relationship with an artist anxious to control his legacy, having seen his reputation plummet after being arrested in 1991 for indecent exposure at an adult movie theater. My first conversation with Paul, he said, I want to direct this documentary myself, and everybodys telling me I cant, and I dont understand why, Wolf recalls. Pee-wee as Himself became as much about the push-and-pull between filmmaker and subject as it was an examination of a complicated performer.

At first, Wolf assembled a film he calls rose-tinted and vanilla. He didnt want to disrespect Reubens, who died unexpectedly of cancer in 2023. But peers who saw Wolfs early cut could sense a certain edginess left in the margins. I always encouraged Paul to embrace his complexity, and I needed to take my own advice, Wolf says. So he put more of himself in the film, which provided opportunities to show Reubens wrestling with how to reveal his full self.

Wolf, whose credits include Recorder: The Marion Stokes Project and Spaceship Earth, interviewed Reubens for roughly 40 hours in total, finding him unbelievably smart and tricky, and at times sweet and at other times cranky. At one point, Reubens walked away from the project. At another, he struggled to find the words to come out as gay, having retreated into the closet in the 80s in an effort to preserve his career. And until Wolf heard the voice message Reubens recorded for him the day before he died, the director had no idea the person hed spent so much time with was sick.

As Wolf and his team recut Pee-wee as Himself, they turned it into both a celebration and a meta dissertation on celebrity. Unlike the highly micromanaged pop star hagiographies that have flooded the marketplace in recent years, the film uses a clear directorial hand to illustrate its stars psychology. That insight, in Wolfs view, is part of why audiences have responded so passionately to Reubens candor.

Hes a generation-defining artist who was torn down by the media and lost control of his personal narrative and completely separated himself personally from his alter ego and was choosing, unbeknownst to me, at the end of his life, to finally share his story, Wolf says. That is unto itself very intense, and I needed to lean into that intensity and to depict it with nuance.

This story first appeared in an August stand-alone issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.