Paul Reubens Wins Emmy for Pee-wee as Himself

The 2025 Creative Arts Emmy Awards celebrated a significant achievement as Paul Reubens won his first Emmy for the documentary ‘Pee-wee as Himself’.

Paul Reubens Wins First Primetime Emmy for ‘Pee-wee as Himself’

The 2025 Creative Arts Emmy Awards concluded on Sunday in Los Angeles, marking a bittersweet milestone: Paul Reubens has won his first Primetime Emmy Award for Best Documentary or Nonfiction Special for co-producing HBO’s Pee-wee as Himself. This two-part film, directed by Matt Wolf, offers fans an unprecedented look into the life, artistry, and resilience of the late comedy icon. Other nominees in this category included Deaf President Now!, Martha, Sly Lives!, and Will & Harper.

Reubens’ Posthumous Recognition

Reubens, who passed away in July 2023 after a private battle with cancer, is the only posthumous winner at this year’s Emmys. This achievement marks his fourth Primetime Emmy nomination and his first victory, adding to his two Daytime Emmy Awards for Pee-wee’s Playhouse in 1988 and 1991.

A Personal Journey for Matt Wolf

For Wolf, this award symbolizes the culmination of a deeply personal journey to tell Reubens’ story. “When you make documentaries, people often ask who your dream subject is. Mine was always Paul,” Wolf shared with Gold Derby. After several unsuccessful attempts to connect with the notoriously private Reubens, a chance meeting through the Safdie brothers eventually led to their collaboration.

Building Trust

However, establishing trust was a significant challenge. “It was a constant struggle to earn Paul’s trust while also acknowledging the limits of his willingness to open up,” Wolf explained. Reubens’ complicated history with the media made him cautious, and Wolf dedicated months to fostering a relationship strong enough to make the documentary possible.

Filming Amidst Adversity

Unbeknownst to Wolf and the crew, Reubens was battling cancer during the filming of the documentary. “I was scheduled to conduct a final interview with Paul the week after he died,” Wolf recounted. “I learned of Paul’s passing on Instagram, just like everyone else.”

Completing the Project

Despite the shock of his passing, Wolf continued with the project, knowing Reubens wanted it completed. “I read the 1,500-page transcript of our interview right after he passed,” Wolf said. “I aimed to honor his legacy under these extraordinary circumstances.”

Exploring Dual Identities

The documentary delves into the delicate balance between Pee-wee Herman, the childlike, irrepressible alter ego, and Paul Reubens, the intensely private man behind the character. “He wanted people to believe that Pee-wee Herman was a real person,” Wolf noted. “Yet, on a deeper level, Paul was very protective of his privacy and anonymity.”

A Revolutionary Legacy

The film traces Reubens’ early years at CalArts, his struggles to break into the entertainment industry, and how rejection from Saturday Night Live inspired him to create Pee-wee Herman. It also highlights his creative partnership with Tim Burton on Pee-wee’s Big Adventure and the groundbreaking legacy of Pee-wee’s Playhouse.

A Moment of Recognition

Reubens’ Emmy win signifies a long-overdue acknowledgment for an artist who blurred the lines between persona and performer. Wolf hopes Pee-wee as Himself enables audiences to see Reubens in his entirety. “Paul Reubens created Pee-wee Herman,” Wolf reflected. “Now that Paul has passed away, I hope people can respect and appreciate the artist who was always present, behind and alongside his creation.”

Pee-wee as Himself is currently streaming on HBO Max.