Paul Reubens: See Photos Of ‘Pee-Wee Herman’ Through The Years: Photos

By:

Elissa Anderson, James Crowley

July 31, 2023 1:50PM EDT

Following the sad news of Paul Reubens’ death, look back on his career from his days at Pee-wee Herman to more recent photos.

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Paul Reubens Through The Years

Paul Reubens Through The Years — Paul Reubens was an icon of children’s TV, best known for playing the character Pee-wee Herman. The actor’s death following a private battle with cancer was announced on Monday, July 31. He was 70 years old. Following his death, he posthumously released a statement. ‘Please accept my apology for not going public with what I’ve been facing the last six years. I have always felt a huge amount of love and respect for my friends, fans, and supporters. I have loved you all so much and enjoyed making art for you,’ he said.

Born in Peekskill, New York, Paul began working in television after completing school at the California Institute for the Arts. After a few appearances on programs like ‘The Gong Show,’ Paul joined the improv troupe The Groundlings, where he began to develop the character that would become Pee-wee Herman.

After a failed ‘Saturday Night Live’ audition, Paul began ‘The Pee-wee Herman Show’ as a live stage show. He became a mainstream star when HBO showed the performance in 1981. He began making many public appearances as Pee-wee, including in films like ‘Cheech And Chong’s Next Movie’ in 1981. The character proved so popular that it led to the movie ‘Pee-wee’s Big Adventure’ and TV show ‘Pee-wee’s Playhouse,’ which ran from 1986 until 1991.

Following a 1991 arrest, Paul avoided the public eye, but slowly began making appearances in other non-Pee-wee-related projects like ‘Murphy Brown’, ‘The Nightmare Before Christmas’, ’30 Rock’, and ‘Blow.’

In 2010, Paul starred in a new version of ‘The Pee-wee Herman Show,’ which ran on Broadway and was taped for HBO. In 2016, ‘Pee-Wee’s Big Holiday’ was released on Netflix. He continued to take on small acting and voice-acting roles in recent years.

Following the sad news of his death, scroll through our gallery to see photos of Paul over the years.

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‘Pee-Wee’s Big Adventure’ (1985)

‘Pee-Wee’s Big Adventure’ (1985) — One of the biggest movies to bring Paul Reubens widespread fame was ‘Pee-wee’s Big Adventure’ in 1985. The film followed Pee-wee on a mission to find his treasured lost bike.

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‘Pee-wee’s Big Adventure’ (1985)

‘Pee-wee’s Big Adventure’ (1985) — Paul Reubens is seen in Pee-wee Herman’s signature gray suit in the debut movie. The character went on to star in three full-length movies.

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‘Batman Returns’ (1992)

‘Batman Returns’ (1992) — Paul Reubens poses for a photo with Carol Kane at the premiere of ‘Batman Returns’ on June 16, 1992. The actor had a minor role as the Penguin’s dad in the Tim Burton-directed movie. Tim also directed ‘Pee-wee’s Big Adventure.’

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Paul Reubens At The 1998 Marlboro 500

Paul Reubens At The 1998 Marlboro 500 — Paul Reubens is seen enjoying the sun at the Marlboro 500 race on November 1, 1998. He had a very different look than his Pee-wee character with a shaved head.

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‘Mystery Men’ (1999)

‘Mystery Men’ (1999) — Paul Reubens starred alongside other major comedic talents like Ben Stiller in the 1999 movie ‘Mystery Men.’ He played ‘The Spleen’ an amateur superhero, who uses farts as his power.

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‘Mystery Men’ (1999)

‘Mystery Men’ (1999) — Paul Reubens is seen in character as The Spleen in ‘Mystery Men.’ The movie follows a team of lesser-known superheroes trying to save the day with ridiculous powers.

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Paul Reubens In New York

Paul Reubens In New York — Paul Reubens sported an all-black leather look as he went to ‘Late Night’ with David Letterman’ in New York. Paul made a bunch of appearances on ‘Letterman’ as Pee-wee Herman.

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Paul Reubens At The 2001 ‘Vanity Fair’ Oscar Party

Paul Reubens At The 2001 ‘Vanity Fair’ Oscar Party — Paul Reubens smiles in a black suit as he attends the ‘Vanity Fair’ Oscar Party on March 25, 2001. While never receiving an Oscar, Paul did get three Primetime Emmy nominations in his life.

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Paul Reubens On ‘The Late Show With David Letterman’

Paul Reubens On ‘The Late Show With David Letterman’ — Paul Reubens is seen with a blue, pinstriped suit heading to ‘The Late Show’ on July 11, 2006. At the time, he took on small roles in a variety of projects.

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‘Reno 911: Miami’ (2007)

‘Reno 911: Miami’ (2007) — Paul Reubens smiles at the premiere of ‘Reno 911: Miami’ on February 15, 2007. He played Rick from the Citizen’s Patrol on the sitcom and reprised the part for the movie.

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‘Pee-wee Herman Show’ (2010)

‘Pee-wee Herman Show’ (2010) — Paul Reubens smirks as Pee-wee Herman on the red carpet for the premiere of the new ‘Pee-wee Herman Show’ in Los Angeles on January 20, 2010. Of course, he wore the classic gray suit and red bowtie.

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‘The Pee-wee Herman Show On Broadway’ (2011)

‘The Pee-wee Herman Show On Broadway’ (2011) — Paul Reubens appears as Pee-wee Herman for his Broadway show in 2011. Here he could be seen sitting in the anthropomorphic Chairry.

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Paul Reubens At The ‘True Blood’ Premiere

Paul Reubens At The ‘True Blood’ Premiere — Paul Reubens smiles for a photo with Cheri Oteri at the premiere of ‘True Blood’ season five on May 30, 2012. He sported a red t-shirt with a black suit.

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‘Pee-Wee’s Big Holiday’ (2016)

‘Pee-Wee’s Big Holiday’ (2016) — Paul Reubens speaks at an AOL event while promoting ‘Pee-wee’s Big Holiday. The Netflix film was the long-awaited followup to ‘Big Top Pee-wee.

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Paul Reubens Heading To ‘Jimmy Kimmel Live’

Paul Reubens Heading To ‘Jimmy Kimmel Live’ — Paul Reubens could be seen walking to a taping of ‘Jimmy Kimmel Live’ on February 4, 2020. He kept his outfit casual for the set visit.

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