We were supposed to be in Central Park. We are not. It’s raining so we’re in Penny Lane’s apartment, shoes off, with a cat named Luna auditioning for the role of “the action,” and Flaco the Owl on the TV behind us. So much for a walking show.

Penny’s deep in what she calls PR season for WILD INSIDE, her new HBO doc about the Eurasian eagle-owl who broke out of the Central Park Zoo in 2023 and spent a year as the most photographed bird in New York. Then she tells us she barely shot it. A volunteer army of Central Park bird photographers had already amassed infinite footage, so Penny’s crew went back and shot the reverse angles — Flaco’s POV of the people watching Flaco — and rebuilt a whole year of seasons to match. “I don’t think anyone understands that we just weren’t there all the time.”

We go long on money and fear. Eight features in, a ninth half-funded, and her first thought is the tenth. That festivals and awards absolutely do matter, whatever people tell you. That this is her worst financial year and she has a hit, simultaneously.

Plus: NUTS! and the Kansas goat-testicle doctor, cornering the cool dad market, the grad school shoot where Ben watched the levels all night and recorded nothing, Letterboxd as the only proof anyone’s watching, EXIT THROUGH THE GIFT SHOP as the film that taught her to make one movie for the 1% and the 99% at once, dirty fuel versus the clean kind — and the thing she can’t stop thinking about, which is how much of the internet is just bots talking to bots.

DISCUSSION LINKS:

WILD INSIDE (2026) | CONFESSIONS OF A GOOD SAMARITAN (2023) | LISTENING TO KENNY G (2021) | HAIL SATAN? (2019) | NUTS! (2016) | OUR NIXON (2013) | EXIT THROUGH THE GIFT SHOP (2010) | TARNATION (2003) | THE PERFECT NEIGHBOR (2025) | MARY OLIVER: SAVED BY THE BEAUTY OF THE WORLD (2026)

TIMESTAMPS:

00:00 We were supposed to be outside 01:15 Introducing Penny Lane 01:23 PR season for WILD INSIDE 02:02 Lynn, Massachusetts and the city of sin 02:58 Newbury Comics and finding culture pre-internet 04:04 NUTS! and the Kansas goat-testicle doctor 05:43 Cornering the cool dad market 07:16 Kindles, hardbacks, and a book a day 08:51 Podcasts ate her reading and her music 10:48 Grad school at UT Austin with Naiti Gamez 11:33 The shoot where she recorded no sound 14:08 Meeting Gabriel Sedgwick and building a crew 16:52 A year spent arranging the art wall 18:40 Competing with the entire Seinfeld catalog 20:00 Four Kenny G albums before a hit 20:50 When did movies become a prestige art form 22:39 The future of documentary, and why AI can’t do it 23:42 Nobody knows your movie is out 24:39 The broadcast era is kaput 25:58 Hunting for her own film on Netflix 28:20 Eight features, a ninth half-funded, already worried about the tenth 30:24 Festivals and awards do matter 31:05 Who paid whom to release the movie 32:40 Not a business, a calling 33:39 The only reward is getting to do the work 34:34 Williams, Hampshire, Colgate, tenure — then quitting 36:07 Dirty fuel and the clean kind 37:40 Stay in shape, paddle out, catch the wave 38:48 Letterboxd as the only feedback loop 41:25 iMovie, mini DV, and TARNATION 44:02 Why she doesn’t care what camera it’s shot on 45:14 How WILD INSIDE was built from birders’ footage 47:18 Shooting the reverse angles 48:46 Rebuilding a year of seasons 50:54 Jeremy finds Flaco first 52:08 How a project actually starts 53:10 Donating a kidney before there was a film 55:45 The film as an imprint of a life 58:13 A hit movie in her worst financial year 59:32 Why a filmmaker runs a Substack 1:02:27 Geeta Gandbhir and THE PERFECT NEIGHBOR 1:04:19 Advice: do what you can do right now 1:05:22 EXIT THROUGH THE GIFT SHOP, the gateway drug 1:06:30 One movie for the 1% and the 99% 1:08:31 Lightning round: is anyone on the internet real 1:09:35 Next time, we actually walk