Thank you Austin Kleon, Carolyn Mary Scott, Louis Venezia, Sean Horlor, Ruth Leitman, Jeremy Workman, Craig Charland and many others for tuning into my live video on Monday with Matt Wolf!
It was fascinating to hear Matt describe his background as a gay teen activist “during Matthew Shepard and Ellen Degeneres” — he was actually the subject of a documentary film in this era (!!), which helped him get a scholarship to NYU Film School, but also turned him away from a certain type of activism.
We also spoke about our shared roots in the community media movement of the early 2000s as well as our shared early commitments to experimental film and video art. Here is the Paper Tiger documentary Fenced Out Matt shouted out as an important artifact of that movement, and here is an incredible series of related events Matt curated for The Whitney Biennial. Other films he mentioned as important to the media activism movement of that era are two directed by Spencer Nakasako: Kelly Loves Tony and A.K.A. Don Bonus.
We discussed his inspiration and process for two of my favorite films he’s directed, his very first, Wild Combination: A Portrait of Arthur Russell (2008) and his most recent (Pee-wee as Himself (2025), both of which are reclamations and reconsiderations of major gay artists. I was struck by how much Matt talked about the primacy of emotion in his storytelling, and how intensely involved we can become in our projects, how each film is a network of relationships as well as a record of that time in your life.
Matt references this shattering piece he wrote for Vulture about why making a film about his childhood hero nearly destroyed him, the complete breakdown of the relationship with Pee-wee, and the book (now in progress) that emerged from that piece. While he’s not actively writing on Substack now, his beautifully illustrated essays collected here are all worth reading.
I am really enjoying these conversations, and hope you are too!
My next live chat will be with Gary Hustwit on March 23.
Gary is a pioneer in so many ways. I first came to his work through the now-classic typography doc Helvetica (2007). I want to speak with him about artistic innovation, developing your own audience, and how he exploded the form of the “music doc” with his film Eno, which uses a custom built (not AI) algorithm to generate an entirely new film with each viewing. I’ve been long eager to see what his digital release looks like. Lo! Behold! Here it is — it’s happening this week, although I’m sure this is just the beginning. Buy a ticket — or buy all 5, because each one will be a different version of the film — so you can come with your own questions for Gary.
