How a love letter becomes a documentary (and vice versa)

Filmmaker Matt Wolf on the making of "Pee-wee as Himself," plus Bloomberg’s report on one city's relationship with a private ICE detention center

by Mark Armstrong

Image for How a love letter becomes a documentary (and vice versa) — Paul Reubens in "Pee-wee as Himself" (photo courtesy HBO)

May 30, 2025

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Dear Storyboard community,

Like any good Gen X-er whose childhood was filled with quotes like "I'm a loner, Dottie, a rebel," I spent the past weekend deeply absorbed in the new HBO documentary, "Pee-wee as Himself," a moving, heartbreaking, and funny portrait of an artist (Paul Reubens) who wholly inhabited a character (bow-tied '80s film and TV icon Pee-wee Herman) and then had his real life exposed to public scrutiny, starting with a 1991 arrest at an adult theater in Florida. (He pleaded no contest to an indecent exposure charge.)

Notably for journalists and storytellers, the film offers a revealing meta-narrative, in the form of Reubens (playfully?) sparring with director Matt Wolf, evading questions, and arguing over control of the story — and at one point halting the project entirely. All the while, Reubens hadn't told Wolf or the producers that he was battling cancer. He died in July 2023, shortly before the filmmaker's last interview with Reubens was to take place.

On camera, the push-and-pull between the filmmaker and his subject makes it clear that each needs the other to bring the project to fruition. For New York magazine, Wolf wrote about how the film came together (and then didn't, and then did). Here's how it starts:

When I approach someone to make a documentary about them, I write a love letter. In the 20 years I’ve been making films, I’ve written countless ones — to Siegfried & Roy, to Marianne Williamson, to soap-opera stars and reclusive musicians. Sometimes I’m appealing to their vanity, sometimes their sense that they’ve been wronged. Always, I end my letters with the same sentence: “Trust shouldn’t be expected. It needs to be earned.”

And documentaries, Wolf writes, require a level of collaboration that can go much deeper than what's required from a regular interview subject:

The dynamic between a documentarian and a subject is tricky. The relationships are more collaborative than people might expect because we documentary filmmakers don’t just need access. We invade the lives of private people with equipment and a crew, and we take their personal photos to scan and digitize. We ask subjects to sign release forms that grant us permission to use their life as the raw material for our work. Paul and I were bonding, but we were also working out how to get what we needed from each other.

Trust is hard-earned in any relationship, let alone in the practice of journalism. It also takes time: Reubens sat for 40 hours of interviews and the film took four years to complete. Even then, Wolf writes, "I remember confiding to [Reubens's longtime assistant Allison Berry] about my struggles with Paul. 'I think he trusts me,' I said tentatively. 'Or maybe he doesn’t, and that’s okay,' she said." The result is a beautiful love letter to an artist who deserved, and got to have, the last word.

Behind the Scenes: Bloomberg examines a private detention center and a town 'Addicted to ICE'

The Torrance County Detention Facility in Estancia, N.M. (AP Photo/Andres Leighton)

Bloomberg reporters Rachel Adams-Heard, Polly Mosendz, and Fola Akinnibi looked at local government agreements with U.S. Immigrations and Customs Enforcement (ICE) to detain immigrants in New Mexico.

[Read the story]

Links of note

#1000WordsofSummer starts tomorrow: Over the past eight years, author Jami Attenberg has created a beloved community and tradition for writers to motivate each other to write 1,000 words a day for two weeks. “Through this project people have: made friends, built cohorts and writing groups, finished proposals and entire books, sold and published those books, and in fact written all kinds of things, but perhaps most importantly, found their voices. I hope that it ends up being meaningful for you in one way or another.” This year’s session runs from May 31-June 13.
"Listening is the hardest art." Julia Barton (2024 Nieman Fellow) chats with "Death, Sex, and Money" host Anna Sale about the life of radio pioneer Mary Margaret McBride, who hosted live interview shows starting in the 1930s. Sale relates her own lessons from both live interviews and edited podcast conversations: "When you are a live interviewer, you have less control over the pacing of how things unfold. So you have to be a more assertive conductor."
In news from Harvard, President Alan Garber received a standing ovation at Thursday’s graduation ceremony when he reaffirmed the university's commitment to international students in the face of attacks from the Trump administration: "Welcome, members of the Class of 2025, from down the street, across the country, and around the world. Around the world, just as it should be." As Nieman Foundation Curator Ann Marie Lipinski shared last week: "Since 1952 when the first international fellows arrived in Cambridge, journalists from around the world have played a vital role in the success and vitality of the Nieman Foundation. Two years ago, in welcoming a reporter from Cambodia, the Nieman family swelled to 100 countries. We cannot imagine the fellowship otherwise and we stand with our international fellows."