Director Matt Wolf Details Struggles Making ‘Pee-wee as Himself’

Pee-wee as Himself director Matt Wolf had his work cut out for him.

Making a documentary film or series is hard enough as it is. Add in a subject with difficult personality and who disappears for months (or even a year) at a time, and you’ve got bonus problems. And just when it seemingly can’t get any more difficult, your subject dies from an illness you weren’t even aware he had.

Paul Reubens put Wolf through the ringer.

So there’s not much The Hollywood Reporter could do to rankle Wolf — especially not on the morning after Pee-wee as Himself won the inaugural outstanding original film, broadcast or streaming trophy at the second annual Gotham Television Awards — but we tried anyway.

This interview has been lightly edited and condensed for clarity.

You recently wrote a very personal essay about your experience making the film, and why you chose to include both yourself and your bouts with Paul — before the very first take, did you think you would be in the film at all?

I never had put myself in a film, and was very reticent to do so. I’m pretty allergic to documentaries in which the filmmaker inserts themselves unless it’s essential to the story. That said, Paul and I had hundreds of hours of conversations in advance of filming the interview, and we started to record our phone conversations early because we thought our relationship reflected aspects of who Paul was. So that idea already existed between us. And then, as we were filming on that first day, and Paul was so rebellious and so resistant to the process, I recognized that it was strong raw material for portraiture to really show who Paul was and how he was engaging in this process.

After Paul died and I was editing the film, I was very rose-tinted in my first cut. Other filmmakers and friends were like, “You need to tell a story about the actual person that you knew, instead of a self-censored version.” That’s when I started to experiment with incorporating myself in ways that were funny but also more barbed. And I understood in that process that this wasn’t about me. It wasn’t narcissistic for me to put myself in the film because it was a device to show Paul’s own wrestling with his decision to share aspects of his private self.

I always recognized there was something there, and we were capturing material that would allow us to get meta in the film. And initially, when I made the film, I thought it might be mean-spirited to include that, but through the encouragement of other filmmakers, I went there and found a way to do it that felt respectful.

So there was a cut that didn’t have you at all?

It had me, but it was a little neither here nor there. I think what people respond to in the film is that, with that device in particular, it shows how controlling Paul was and how ambivalent he was about being known and being the subject of a documentary. And I think I initially used it just as funny anecdotes, kind of like schtick between him and I. Most of the exchanges between us are funny. They had a bite to them that I was self-censoring for a while.

What has the reaction been from the filmmaking community in your choice to keep those moments in?

Everybody sees how hard [making the film] was, particularly filmmakers. And then I wrote that essay, which I wanted to do for a while, and a lot of filmmakers reached out because it it reflected experiences they’ve had that aren’t often discussed publicly.

Paul is an executive producer on the film. Do you believe the inclusion of your spats with Paul help separate this documentary from what people pejoratively refer to as “vanity projects”?

Yes and no, because I don’t think we know when a subject is an executive producer on a film. I don’t think anybody knows what that means because there’s no blueprint for it. And I think more and more viewers are skeptical of projects that feel like they’re vanity exercises. Why wouldn’t somebody feel that way? Why wouldn’t they feel like, “I wish this person could kind of cede control so that I could see them with nuance and complexity,” because that’s what makes a documentary subject compelling, not just their notoriety. Sophisticated subjects understand that their complexity is what is appealing and compelling.

I’m not a documentary subject, I don’t understand fully the motivators for putting yourself out there, and I don’t understand the motivators for censoring or limiting the amount to which you’re willing to share. But I don’t presume to understand what the arrangements are between filmmakers and their subjects. And I also think that people, particularly journalists, assume that we have some sort of separation of church and state that we just don’t have. Documentary filmmakers, we need so much stuff from our subjects that you don’t need while interviewing us as a print journalist, and that the idea of not getting close to your subject who you’re intimately filming is completely unrealistic.

The idea of maintaining a level of trust in which that person understands that what you’re doing is in service of a broader goal that likely is based in shared interests — I don’t think that’s compromise. I think that people, when they make films, need to be transparent for the most part about what they’re doing, and that in that transparency, there should be a certain level of respect for the autonomy of the filmmaker. Granted, I don’t make films that are hit pieces or “gotchas,” and there are all sorts of public figures who should be hit or should be the subject of a “gotcha” investigation, but it’s asking a lot for that person to be intimately involved in a project and then to betray them in that sense.

The conversation about vanity projects and the conflict of interest, there’s a certain lack of nuance about that. What does it look like to tear down someone you were intimately involved in filming versus what does it look like to basically be employed by them and to service their interest for public relations? I don’t think things are that black and white. Things exist on a much more nuanced spectrum.

As depicted in the documentary, the was a lot of starting and stopping on the project — often with long breaks — did you ever regret even beginning the film?

No, no, I definitely wanted to make the film. I felt like I had gotten in so deep and there was no turning back. And I felt trapped. It was a situation that felt out of my control.

It must have been scary though, not knowing if it would ever be completed.

Well, it was unbelievably difficult. It wasn’t, like, chill. I wasn’t like, at peace about that. I was very, very tormented by the uncertainty about whether this film would exist or not. I had never poured myself into a project like I had with this — it could have been devastating.

I did lose hope (at times) that the project would come to fruition. I hoped that he and I could move forward in our lives in a way that would not be tormented by the status of this project.

You are a big Pee-wee Herman fan. Did the difficult nature of working with Paul end up being a never-meet-your-heroes situation for you?

No, because Paul is so different than Pee-wee. Pretty quickly after interacting with him, he’s just a separate person. I didn’t feel a prolonged starstruck-ness with him, because he was someone who I intuitively felt I would have a connection to, which I did, but was in some ways disconnected from the thing that I had fandom for.

Also, I’m not like a big fan type. I’m more someone who can separate my admiration and fascination with somebody’s work from them as a person. So it wasn’t really that. It was more like I had met my match, someone who was not necessarily going to be receptive to the things I normally do to gain trust from somebody or to kind of get my way. But also, I dreamed of doing the most difficult project possible, and I, to some extent, was cocky or in denial that it wouldn’t be as difficult as it was.

Paul died before your final interview(s), which were to include him discussing his arrests, took place. Is Pee-wee as Himself a complete documentary?

Yeah. I mean, I’m not a speculative person. People ask me, “What would you have asked in the final interview?” I had prepared the final interview, I know what I would have asked — but I don’t know why Paul didn’t conduct that final interview. Obviously, there was a whole constellation of things going on that I was unaware of, but Paul shared what he was able to share on the timeline in which he was able to share it, and it was extraordinary to have that material.

Documentary filmmakers, we traffic in the limits. We have a limited amount of material. There’s always things missing. You can’t have everything. It would be selfish to think that you could have everything. This film was an embarrassment of riches. I had 40 hours of interviews with my subject and over 1,000 hours of archival footage, and the idea that that’s not enough is greedy. So, I don’t feel the film is incomplete. I feel that the film is tragically complete.

Did you get the impression that Paul was waiting to die to not do the interview about his arrests?

No, I don’t know. I don’t know what was motivating Paul during our conflict, and I don’t know— what I do know is that he was motivated for the film to be finished. He made sure that that was known and before he died. I just didn’t, at the time, understand what was going on.

You don’t feel like you got played.

No, not at all. I feel like I was trying to do a project with somebody who was going through a lot of things I was unaware of that made what already was an intense process much more intense, and that I got clarity that my subject, Paul, wanted this film to be completed, and I took that responsibility very seriously.

Having gone through this experience and coming out successfully on the other side, do you think your next projects will feel easy?

I do feel that way a bit, but also this film was a once-in-a-lifetime situation. Both because of who Paul Ruebens was to the world and to me, and because of the extraordinary access that I had, and also kind of unforeseen circumstances of Paul’s death. There is not going to be another film in which I am working with a extraordinarily-controlling subject who then passes away and I’m granted total creative freedom to render a complex portrait of that person. I don’t expect other films to have stakes as high as this one had.

When I watch this film, it’s a very emotional experience. I’m learning as the film has been released that it is also emotional for the people who watch it. And that has been, I guess, a little surprising to me. I just didn’t understand how the intensity of feelings that I felt having gone through this relationship and through this process would translate so directly to the viewer. And that seems to be what’s happening.