Alison Stewart: This is All Of It on WNYC. I'm Alison Stewart. If I say, "I know you are, but what am I?" Or, "Everyone I know has a big but." Better yet, here's the man himself.

Pee-wee Herman: Hello, Dottie? It's me, Pee-wee.

Dottie: Where are you calling from?

Pee-wee Herman: Texas!

Dottie: Where?

Pee-wee Herman: Honest. Listen, I'll prove it. [sings] The stars at night. Are big and bright.

All: Deep in the heart of Texas.

Alison Stewart: Pee-wee Herman, aka Paul Reubens, was a performance artist, a clown, a serious soul. You get to see all sides of him in a new documentary called Pee-wee as Himself. The film debuts on HBO this Friday, and it almost didn't get made. For the previous six years, Reubens had been privately battling two forms of cancer, and he died in 2023. During that times, Reubens was being interviewed for a documentary about his life and career, but not even the filmmakers were aware of his diagnosis.

In the two part documentary, Pee-wee as Himself, Reubens doesn't discuss it, but he does talk about many other aspects of his life in unprecedented detail. His childhood, his time with The Groundlings, his relationship with a man. The documentary was directed by my next guest, Matt Wolf. Hi, Matt, thanks for coming to All Of It.

Matt Wolf: Thanks for having me.

Alison Stewart: The documentary begins with a card that mentions, unbeknownst to the filmmakers, he had been fighting cancer for years. What was your immediate reaction to that news and learning the cause of his death?

Matt Wolf: Oh, it was a total shock.

Alison Stewart: Yes.

Matt Wolf: I had no idea. Paul and I were scheduled to do a final interview a week after he passed away. We had a conversation that I could tell something was off, but I certainly didn't have a sense of the gravity of what was going on, but Paul gave me the assurances that we could move forward with the project, and I found out on Instagram, along with the rest of the world.

Alison Stewart: After his death, and after thinking about it as a whole, it's a three-hour documentary, two parts, how did the purpose of the documentary change, if at all?

Matt Wolf: In some ways, it didn't change. The day that Paul died, I started to read the 1,500-page transcript of our 40-hour interview, and certain things that he said had, I guess you could say, enhanced significance in the context of his death, but my mission from the beginning was to do a complex and nuanced portrait of an artist. Paul's mission was to set the record straight and to overcome the media controversies that had become unfortunate footnotes to his career. Those goals hadn't changed, but the level of profound responsibility I was grappling with was quite different.

Alison Stewart: It's interesting because your goals, they seem like they would be the same, but at times during the filming, it was interesting. The two of you kind of not went at each other, but went around it.

Matt Wolf: Yes, there was a power struggle throughout the making of the film. Paul was somebody who lost control of his personal narrative in the media. Of course, he had reservations and skepticism about a filmmaker, like myself coming in, and saying, I'm going to have final cut. I'm going to take your life story and make it the raw material for my work. That concern he had didn't go away. In fact, the first time I met Paul, he said something very similar to the opening of the film. I want to direct this film myself, but everybody's advising me against it, and I don't understand why.

When we began this epic interview, Paul was rebellious against the process of being led, the way you're leading me right now. He didn't like that. The ways in which he rebelled initially were frustrating to me. Then I thought, hey, this is portraiture. While this film covers things that happened in the past to Paul, this is him relating to telling his story in real time in the present. He may be in conflict with me, but really he's wrestling with himself to decide how much to share.

Alison Stewart: It also showed us what he was feeling, what he was thinking during the course of the interview. It wasn't just question, answer, question, answer. It was like you saw him thinking about it.

Matt Wolf: Yes. I think many public personalities have been interviewed many times as themselves, and they're familiar and have a certain way of framing the narrative of their life. Paul, to some extent, had done that but very little. The things that he was sharing were vulnerable and intimate in a way that he had never been before. Of course, there was a kind of internal struggle in that process, and the way we work that out is by talking on camera for just an incredible amount of time that I don't know many filmmakers who have had that experience with subjects.

Alison Stewart: I'm talking to director Matt Wolf about the two-part documentary Pee-wee as Himself. It drops on HBO and Max this Friday. We go all the way back to his childhood. He really liked The Little Rascals. He loved I Love Lucy. What did you learn about Paul Reubens from his media consumption that he took in as a kid?

Matt Wolf: Well, I think I got a sense of who he was generationally in terms of what his kind of touchstones were, like Pollyanna and the young Disney stars. To some extent, it's not surprising that classic TV shows like Captain Kangaroo were an inspiration to the maker of Pee-wee's Playhouse. I think what became more interesting was the activity he was involved in in the late 1970s, particularly at CalArts, an art school known for conceptual art, where Paul really trained as a performance artist.

He would continue that when he fell into The Groundlings, which was an improvisation troupe, but at a point in the entertainment industry where comedy wasn't necessarily king, that wasn't the stepping stone to a huge career in movies. He also was adjacent to the punk scene that was taking place on Melrose in Los Angeles. In fact, The Groundlings was next door to the most famous punk record store called Vinyl Fetish. All of these things from the classic TV shows like I Love Lucy to performance art to punk, it all collided into Pee-wee Herman, and I just found that fascinating.

Alison Stewart: His dad was a pilot in the Israeli Air Force. He seemed like a real bit of a character. He described his parents as being a vaudeville team when they were together. What was interesting to you about the way that Paul Reubens talked about his parents and his family?

Matt Wolf: I think Paul loved his parents, and intensely idealized his father as this larger-than-life figure who he called macho more than a few times, but he called him swaggering, like Indiana Jones. I think that Paul, like many gay people, felt a need to prove himself to his father and live up to his father's expectations, and kind of ideas about success. Paul was just enormously driven, unabashedly ambitious. I don't think that was driven by his parents, but I do think that Paul was preoccupied with his father's approval. That was clear to me.

Alison Stewart: You interviewed his sister in the film. She's a civil rights attorney. She took a more serious path as a civil rights attorney. What was similar about the two of them, and then what were their differences?

Matt Wolf: They both are gay, and both stubborn and hot-headed. It's hard to make that comparison. I think Abby had a great appreciation for Paul, and they also had distance in their differences. Abby, I think, was perplexed by Paul's decision to live as a closeted person. I think she wished that he would be in a traditional gay relationship and would be out, but also recognized that in some ways that was a survival strategy for Paul to truly embrace the ambition that he possessed.

Alison Stewart: Yes, and the film towards the end, one of his friends says, he didn't really talk about his sexuality very much, but he did talk about it with you. Were you surprised?

Matt Wolf: Well, when Paul started the documentary with me, we had literally hundreds of hours of conversations leading into that interview. Right away, he said he wanted to come out. I'm a gay filmmaker. I think that was a point of affinity between us. It also was a point of tension. Paul, while he did want to come out, did not want to be characterized as a gay icon, or he didn't want the film to be made entirely from a queer lens. I think I had concerns that I might do that.

When I heard the story of his early relationship with a painter named Guy, I was struck by how emotionally intense that relationship was, and also what Paul did when they broke up. Paul decided to go back into the closet to pursue his career because that was something he could control. It was very poignant, but to me, it also was hugely significant. In some ways, Paul became two different people in that moment, which would foreshadow the creative and professional choices he made while he separated himself from Pee-wee Herman.

Alison Stewart: Please, correct me if I'm wrong. Did you reach out to Guy, or Guy--

Matt Wolf: Guy passed away-

Alison Stewart: He passed away.

Matt Wolf: -from AIDS-related illness.

Alison Stewart: That's right.

Matt Wolf: Paul saw him several hours before he passed away. It's a very poignant story and moment in Paul's life that I think had a huge impact on him over the decades.

Alison Stewart: It was so interesting. He often said that parts of Pee-wee were parts of Paul, the way that Paul used to be, like, mm, chocolaty.

Matt Wolf: Oh, you mean Guy. Guy, the boyfriend.

Alison Stewart: Guy, sorry.

Matt Wolf: Yes. I think a lot of artists crib things from real life, and Guy, I think, inspired aspects of that character. Well, I know so, because Paul said so.

Alison Stewart: He wanted to be a dramatic actor, at least in part. When did he find comedy? When did he decide, you know what, this is right for me?

Matt Wolf: Well, Paul wasn't having success as a dramatic actor. As a teen, he was sort of the resident juvenile at this prominent regional theater company in Sarasota, Florida. He found himself at CalArts by accident and trained in performance art, and I think kind of saw a path of being an underground performer, but Paul had more mainstream aspirations. When he wasn't getting cast in roles besides being on The Gong Show--

Alison Stewart: That was hilarious.

Matt Wolf: Yes, it is. He did amazing stuff on The Gong Show.

Alison Stewart: Amazing.

Matt Wolf: That was a dead end. I think he realized that he was funny and to go with it. At the time, comedians like Andy Kaufman were doing comedy in a way that intersected with performance art. People like Robin Williams were getting television specials. Paul saw that as an avenue, and that's when he discovered The Groundlings, which really changed his life and gave birth to that character.

Alison Stewart: It was so interesting. I never knew that he and Phil Hartman were such good friends.

Matt Wolf: Yes. It was Phil Hartman, Paul, and a comedian named John Moody, who really were this holy trinity within The Groundlings, the real breakout stars, and they all collaborated intimately on the creation of The Pee-wee Herman Show, the midnight show that Paul would put on there.

Alison Stewart: That show looked like it was a riot. Like in the early days, it was so raw. It was so out there. What was the original response to it, that one-man show?

Matt Wolf: The initial show, which wasn't a one-man show. It really was the product of collaboration with all these other gifted improvisers and punk artists like Gary Panter. The original response, I think, immediately was ecstatic. It was something that clearly was becoming a cultural phenomena immediately. I think it was because Paul and his collaborators built a full world. They built a world for his impish character to live in and a constellation of characters who brought out this sweetness and subversiveness that came to characterize Pee-wee's world.

Alison Stewart: I wanted to ask you about Gary Panter. Would you explain to people who he was?

Matt Wolf: Gary was initially a graphic designer who got involved in record labels, but he became the preeminent artist of the punk movement in Los Angeles, and just made some incredible logos and album covers, but also comics like Jimbo. Paul would go to Vinyl Fetish, the record store next door to The Groundlings. He loved everything Gary did. He asked him to make a poster for his play, and Gary said, I want to design the whole thing. What Gary made became, in some ways, a blueprint for Paul's children's television show, Pee-wee's Playhouse.

Alison Stewart: In playing Pee-wee Herman, he made a decision to become Pee-wee Herman, even on The Dating Game as Pee-wee Herman. Why was it important for him to give over himself to Pee-wee?

Matt Wolf: Well, Paul always said to me, I wanted people to believe that Pee-wee Herman was a real person, and that's why Pee-wee was a conceptual art project. Part of the early experiments with that notion was to bring Pee-wee out into the wild, and The Dating Game was his first experience with that. He, in the film, recalls going to the audition for the show in character as Pee-wee, and everybody just looked at him immediately. They gravitated to him like a magnet. It's hilarious to see him being chosen as the winner of the show. Spoiler alert. I think he started to realize the character isn't as good or as strong if people are thinking about Paul, and he abandoned the career of Paul Reubens to focus on the career of Pee-wee.

Alison Stewart: That's why it was like performance art. The character of Pee-wee was performance art.

Matt Wolf: Yes. When Paul really started to get known by a national audience, it was when he appeared on the early David Letterman Show, and he became a sort of regular who would do these kind of skits that would be in front of rear projections and green screens. Him and David had an incredible rapport, but as Paul says in the film, he was doing performance art in mainstream pop culture. That was unprecedented to the extent that he was doing it. That artistic ingenuity coupled with the level of ambition that Paul held, it really broke new ground.

Alison Stewart: How did Paul Reubens deal with the idea that Pee-wee became very famous, but Paul wasn't as famous?

Matt Wolf: Begrudgingly. I think that Paul at once appreciated his anonymity, and also had an ambivalence about the fact that people didn't know who Paul Reubens was. When the title for the film Pee-wee as Himself comes from his credit in his debut film, Pee-wee's Big Adventure, in the end credits, it says Pee-wee played by himself. When Paul's writing credit came up with Phil Hartman and Michael Varhol, nobody knew who Paul Reubens was. That was a source of tension for him, particularly with Tim Burton, who would go on to have this enormous career as a film director, but not everybody knows that Pee-wee's Big Adventure was his first film when he was 26 years old.

Alison Stewart: I'm talking to director Matt Wolf about the two-part documentary Pee-wee as Himself. It drops on HBO and Max this Friday. In the 1990s and 2000s, Reubens faced two media scandals and arrests for indecent exposure in adult cinema, and later mistaken charge of child pornography. How did these arrests and the scandal around them and everything, how did it break down the wall between Pee-wee Herman and Paul Reubens?

Matt Wolf: It was devastating for Paul, obviously, but he had spent his entire career so diligently creating this separation between Pee-wee Herman and Paul Reubens, and that really worked for him, and then it didn't. The world met Paul Reubens through this scary mugshot. It was a worst case scenario for him. What Paul would say to me is that he was in a prolonged state of shock. I think it was years of really just being in a kind of state of shock about the consequences of what happened. We look at it now and think of that initial incident as being pretty provincial, but this was the early days of the media's growing appetite for salacious takedowns, and Paul was an early casualty of that.

Alison Stewart: You were born just a couple of years before Pee-wee's Big Adventure was released. What did Pee-wee Herman mean to you before you started this film?

Matt Wolf: Well, I came of age on Pee-wee's Playhouse, and I wouldn't have been able to put words to it at a time, but I think it was really my first engagement with art that I had a strong emotional relationship to. I was transfixed by that television show. I had that kind of iconic Pee-wee pull string doll, and it dangled above my bed all the way through my adolescence. I looked at it every night before I went to bed, and high school photography class, I took a picture of him, and that photo still hangs on my refrigerator today.

Pee-wee became, in some ways, an intuitive touchstone for me, even if I hadn't, in specific terms, analyzed why. Paul Reubens remained a point of fascination because he was unknown. I often make films about people who might be called unconventional visionaries, and I like to do a reappraisal. While Pee-wee was well known, Paul wasn't. In some ways, he fit into my wheelhouse.

Alison Stewart: All right, the film airs. Somebody wants to make a version of this film, a fictional version. Who would you want to play Pee-wee Herman? I have my choice, but who would you want to play Paul Reubens?

Matt Wolf: Oh, God, I have no idea. I'm sure there's some 3D scan of Paul, and that he would prefer to play it himself. I don't know. I can't speak for him, but he was a big Timothée. Okay, I buy it.

Alison Stewart: Timothée Chalamet playing Paul Reubens?

Matt Wolf: I can see that. He wears those little bow ties sometimes for those award shows.

Alison Stewart: I was thinking about, like, just watching the first half of the film. He was good looking. He was like a gorgeous guy.

Matt Wolf: Oh, he was gorgeous, yes. He's beautiful. Some of the best archival is by Paul's friend Ann Prim. These gorgeous photographs of Paul and his gender-bending friends in high school in Sarasota. They look like they're shot out of the Warhol factory. In fact, all of them were obsessed with Andy Warhol. There's just some revelatory, incredible archival footage from a period in which nobody has seen Paul. It's also very rare that archival exists from that late '70s period in these art scenes. Paul, yes, he was a just magnetic, compelling person across all eras of his life.

Alison Stewart: I'm telling you, Timothée Chalamet, watch it this weekend. I am talking to director Matt Wolf about the two-part documentary Pee-wee as Himself. It drops on HBO this Friday. Thank you for coming to the studio.

Matt Wolf: Thank you so much for having me.