Paul Reubens Tells His Story in HBO’s Two-Part Pee-wee Herman Documentary – Trailer

HBO Original two-part documentary ‘Pee-wee as Himself’ debuts May 23.

HBO is set to premiere the original two-part documentary Pee-wee as Himself on Friday, May 23, from 8:00 p.m. to 11:20 p.m. ET/PT. Both parts will air back-to-back on HBO and will be available to stream on Max. Directed by Matt Wolf (The Stroll), Pee-wee as Himself offers an intimate and unfiltered look at the life of the late Paul Reubens, best known as his iconic alter ego, Pee-wee Herman.

The film is largely driven by a candid interview with Reubens, filmed before he died in 2023, in which he opens up about his personal journey, the evolution of Pee-wee, and the impact of his decades-long career in entertainment.

Compiled from over 40 hours of interviews, 1,000 hours of archival footage, and tens of thousands of never-before-seen photographs, the documentary explores Reubens’ roots in Sarasota, Florida, his early exposure to circus culture, and his training at the California Institute of the Arts. His creative spark ignited at the Los Angeles improv group The Groundlings, where he developed Pee-wee Herman — a character that would go on to define his public identity and shape a generation of pop culture.

Back-to-back premiere.

The first part of the documentary (8:00-9:40 p.m. ET/PT) follows Reubens’ childhood dreams of becoming an actor, inspired by shows like Howdy Doody, Captain Kangaroo, and I Love Lucy. It tracks his rise from avant-garde performer to breakout star with the success of Pee-wee’s Big Adventure in 1985. As fame swells, Reubens increasingly hides behind the Pee-wee persona, struggling with the pressures of living in character.

The second part (9:40-11:20 p.m. ET/PT) dives into the creation and cultural significance of the Emmy-winning Pee-wee’s Playhouse, which celebrates inclusivity and imagination. It also addresses Reubens’ legal battles and the intense media scrutiny he faced in the early 1990s.

Through it all, Reubens remains resilient, making a comeback with a Broadway show, guest appearances, and a final Pee-wee film — all while refusing to let controversy overshadow his contributions to entertainment.

The film includes interviews with close friends, collaborators, and artists who helped shape Pee-wee’s world. Featured voices include Reubens’ sister Abby Rubenfeld, artists Gary Panter and Wayne White, and actors Lynne Stewart, Laurence Fishburne, Natasha Lyonne, and S. Epatha Merkerson. Filmmakers Tim Burton and Judd Apatow also reflect on their time with Reubens.

At once funny, emotional, and eye-opening, this documentary captures the full spectrum of Paul Reubens’ life — a man who never stopped believing in the power of joy, imagination, and being unapologetically different.

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