How the Director of Pee-wee as Himself Convinced Paul Reubens to Finally Open Up

Time​ Magazine

23-05-2025

On July 31, 2023, Matt Wolf received news that no documentarian wants to hear: The subject of his uncompleted film was dead. This was no mere talking head. It was a man who left an indelible mark on pop culture, whose manic persona, gray suit, and bowtie helped define the 1980s. On a personal note, says Wolf, it was someone who 'changed who I was through his art.' The subject was Paul Reubens, the actor best known as Pee-wee Herman, who had been diagnosed with cancer six years prior.
'Paul was very preoccupied with the film being finished before he died,' says Wolf, whose two-part HBO documentary, Pee-wee as Himself, debuted at Sundance to rapturous praise and premieres on May 23 on HBO and Max. Though Reubens never said his death was imminent, or even told Wolfe of his cancer diagnosis, his legacy was clearly on his mind. 'Every day I woke up saying, 'You must rise to the occasion. Do not drop the ball,'' says Wolf, whose previous documentary subjects include the musician Arthur Russell and the Biosphere 2.
Reubens was, according to Wolf, intense, complex, and 'the funniest and one of the smartest people I've ever met.' He was also a 'resistant subject.' That resistance plays out onscreen and distinguishes Pee-wee as Himself from other celebrity bio-docs. This one tells, but it also shows. The telling comes via recollections from Wolf's talking heads—drawn from 40 hours of interviews with Reubens, plus friends, family, and colleagues—as well as Reubens' career archive, including 1,000 hours of video footage and tens of thousands of images. These take us from Reubens' early life as a precociously creative child growing up not far from the Ringling Bros. Circus headquarters in Florida, through his work in the improv group the Groundlings, to his career successes: creating and starring in the hit 1985 film Pee-wee's Big Adventure and practically rewriting the book on children's programming during the five-season run of his Saturday morning CBS show Pee-wee's Playhouse.
Where the doc shows rather than simply tells, however, comes when Reubens breaks the fourth wall about the process of making it, including wanting to be more hands-on with the production and his suspicious regard of Wolf. The tension is palpable. At one point, Reubens tells Wolf that he made 'one documentary that I liked out of, what—six?' 'There were times I was angry at Paul,' recalls Wolf. 'I accepted this was great material for the film, and he knew it.'
Reubens, who admired people 'living conceptually' during his college days at California Institute of the Arts, had devised Pee-wee as a character meant to exist in the real world as well as showbiz. He was often billed as Pee-wee Herman during interviews and in movies, rarely letting his real self show in service of his full-time performance art piece. For Wolf, the trick was to pull back the curtain on the performance to reveal the man himself.
Reubens was Wolf's 'dream subject.' They connected in 2020, during the height of pandemic lockdown, after Wolf caught wind that Reubens was interested in making a film about his life. So began a series of FaceTime and Zoom interactions that would number in the hundreds of hours. 'With Paul, there was no 15-minute conversation,' Wolf says. Reubens, unsure whether Wolf was the right guy for the job, proceeded begrudgingly. And then one day, the resistance just abated. 'He said, 'I'm in. Sometimes you gotta take a leap of faith,'' remembers Wolf.
Though the line between director and subject was fixed, Wolf nonetheless considered Reubens a collaborator. But the question of just how much Reubens was to contribute added to the strain. Before Wolf had completed his interviews, Reubens went incommunicado. 'We were at an impasse as to what post-production would look like, and I was holding my ground that I would be doing that independently, and that he would have opportunities to see the cut,' says Wolf. 'And that didn't feel like enough to him.'
'Paul was very particular,' says Cassandra Peterson (better known as Elvira), who befriended Reubens in the 1970s when both were in the Groundlings and who appears in the doc. 'He wanted to control things, and have things exactly the way he wanted, to a really extreme degree. So I kind of felt sorry for the filmmakers. I knew it would be a tough road.'
Peterson recalled falling out with Reubens due to a work issue that she did not specify. It happened not long after the 1986 debut of Pee-wee's Playhouse and lasted for years until they found themselves reunited while presenting an award together. 'It was great to be friends with Paul,' she says. 'He was funny, brilliant and a fantastic friend, but I really had to separate the work from the friendship.' She expressed great admiration for her friend's creativity. 'One of Paul's strong points was remembering how he was and what happened to him as a child,' says Peterson. 'He kept ahold of that childhood thing that everybody wishes they could hold on to. The freedom and creativity that you had when you were a child, Paul never let that go.'
Wolf was initially reluctant to include his own presence in the movie, but he and Reubens decided together to explore their dynamic on-screen. Control was a frequent topic behind the scenes and in front of the camera, where Reubens openly pondered if he should be the one making the film. Wolf attempted to shoot candid footage of Reubens to augment the talking-head material, but it didn't work. 'If anything that wasn't planned happened, he would be unhappy,' Wolf recalls. As to Reubens' need for control, Wolf has some theories. 'Many exceptional artists are incredibly controlling,' Wolf says. But also: 'He was controlling because he lost control of his personal narrative in the media.'
Wolf is referring to two arrests that resulted in career-upending scandals. The first occurred in 1991, when Reubens was picked up in an adult movie theater in Sarasota, Fla., and charged with indecent exposure. This resulted in the effective cancellation of Pee-wee's Playhouse; he pleaded no contest and maintained publicly that the allegations were false. The second happened in 2002, when Reubens was charged with possession of child pornography. He eventually took a lesser plea of obscenity, while maintaining that nothing in his archive of vintage gay erotica constituted child sex abuse material. The impasse between Wolf and Reubens occurred before Wolf got to ask about these arrests in detail. Those parts of the movie are largely told through the recollections of his friends and family.
Wolf did capture Reubens discussing his sexuality, which Reubens had never done publicly. Though he had relationships with men, he was closeted for the sake of his career. In the film, Reubens seems at ease discussing his life as a gay man, but Wolf says the filming of that interview 'was not a chill, easy day.' Sexuality was both a point of connection and tension among director and star. Wolf, too, is gay, but came out at 14 and values his sexuality as a key feature of his identity, a position Reubens didn't share. When Wolf engaged Reubens about his sexuality, he noticed his subject was 'squirmy and procrastinating a lot' then spoke only in vague terms. Finally Reubens took Wolf aside and said, 'I don't know how to do this.' To that, Wolf had a simple directive: 'Just say, 'I'm gay.'' Once the cameras were back rolling, Wolf asked Reubens point blank, 'Are you gay?' Reubens joked and then 'snapped in,' discussing his sexuality freely. 'It was extraordinary, and I felt very proud of him,' Wolf says.
In July 2023, Wolf and Reubens resumed communication and agreed to proceed with the shoot. But the interview they planned never came to pass—Reubens died at 70 just two weeks later. Peterson says she was aware of the cancer 'from day one'—Reubens had called her crying the day he received his diagnosis of lung cancer. But he fought it and seemed to recover completely only to find out that he had a brain tumor some time later. Treatment for that also seemed to go well. 'He never dwelled on it,' Peterson recalls. 'He never talked about it. He ate healthy. He really turned his life around.' But then maybe a month or two before his death, Reubens told her that he wasn't feeling well. 'He'd had a few episodes of feeling sick, and I was getting worried,' she says.
As indicated in the documentary, Reubens left behind a partner when he died. Peterson could not recall how long they were together before Reubens' death, but she said that their bond was undeniable. 'It was the first time I heard Paul talk about somebody who he really, really liked,' she said. 'It was nice that Paul had somebody at the end, a very nice person who really cared about Paul. I was so happy to see that.'
The day before he died, Reubens recorded a voice note in which he reflected on his 2002 arrest and sent it to his publicist, Kelly Bush Novak, who passed it on to Wolf. Toward the end of the film, a frail-voiced Reubens says, 'More than anything, the reason I wanted to make a documentary was to let people see who I really am and how painful and difficult it was to be labeled something that I wasn't. The moment I heard somebody label me as, I'm just going to say it, a pedophile, I knew it was going to change everything moving forward and backwards.'
Reubens' death put Wolf in a shaky position. He pushed down feelings of grief in order to finish his film. The stakes couldn't have been higher. 'I've never felt so trusted to take on such a big thing,' Wolf says. Peterson loves the resulting film. 'I really felt like Matt got Paul. He had a handle on what he was doing,' she says.
The documentary is an honest portrait of a creative technician, his drive, his process, and the way he negotiated life in the public eye. The film rather explicitly asks a question that has preoccupied the culture on conscious and subconscious levels in the age of social media and scorn for traditional media: Who gets to tell people's stories? It seems clear that, had Reubens been in creative control, we wouldn't have seen the glimpses of his humanity that, while not always flattering, make Pee-wee as Himself so riveting. And, while they might not have been what Reubens wanted, they are the product of the deep respect and admiration Wolf had for his subject. 'I was determined to make meaning out of this,' says Wolf. 'I said to Paul, 'I will do right by you.' I meant it.'