by Steve Dollar | May 22, 2025

Iconic Comedians and Directorial Debuts: May in Florida Film

Film critic Steve Dollar explores Pee-Wee Herman's legacy and the future of Florida film

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Pee-Wee as himself cover art
“Pee-Wee as Himself,” as documentary series released two years after Paul Reubens’ death, airs in late May on HBO. Photography courtesy of HBO

Growing up in Sarasota, the young Paul Reubens became obsessed with the Ringling Bros. and Barnum & Bailey Circus, which wintered there, and later joined the Asolo Theater, renowned as the largest repertory theater in the Southeast. Years later, Reubens would discover film fame under another guise: bow-tied manic manchild Pee-Wee Herman.

Before his untimely death two years ago, the subversive comic mastermind spent considerable time with filmmaker Matt Wolf (“Teenage,” “Spaceship Earth”), peeling back the layers of his life for the new HBO Max documentary “Pee-Wee as Himself.” The two-part portrait piece offers Reubens a chance to reveal facets of his real self—obscured by his public persona as the impish actor and Emmy-laden children’s TV show host Pee-Wee Herman—and look back on a career derailed by a 1991 indecent exposure arrest inside an adult movie theater in his hometown.

“He wanted to really set the record straight and overcome some of the controversies from his arrest,” Wolf told The Daily Show recently. “And I said, ‘Well you know, that’s the easy part. The harder part is to really look inward. Who are you really as a person? The world doesn’t know, even though your character is so iconic.’”

Another Florida native getting some high-profile attention is Miami filmmaker Paula Gonzalez-Nasser, whose debut feature “The Scout” premieres next month at the Tribeca Film Festival, New York’s sprawling summer showcase that flaunts a lot of shiny celebrity photo ops—but also offers a launchpad for promising indie filmmakers from around the world. Gonzalez-Nasser, now a Brooklyn resident, is aligned with a cluster of fellow Florida State University film school grads who have put together low-budget comedies like Ryan Martin Brown’s “Free Time” and Justin Zuckerman’s “Yelling Fire in an Empty Theater.”

The story is based on Gonzalez-Nasser’s own experiences breaking into the film industry when she first moved to New York. “I thought it looked like an easy job,” she says, “but it quickly turned out to be a really interesting, intricate job of (picking up on) social cues and learning how to talk to people and getting them to trust you.” The filmmaker filed away her most colorful encounters with an array of strangers she met, scouting for Brooklyn-shot productions like “Search Party,” “Broad City” and “High Maintenance,” and the film “Never Rarely Sometimes Always.”

“I would always leave those appointments (thinking) that felt like such an interesting scene, where it had a beginning, a middle and an end,” Gonzalez-Nasser says. “And there was such a weight to those interactions that I thought would be interesting to kind of fictionalize.” Look out for “The Scout” as it takes to the festival circuit following its Tribeca premiere—and expect a lot more to come from Gonazalez-Nasser and her partners.


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