As the stage performance gained further popularity, Reubens took the character to motion picture with Pee-wee's Big Adventure in 1985, toning down the adult innuendo for the appeal of children.

In June 2007, Reubens appeared as Pee-wee Herman at the Spike TV's Guys' Choice Awards for the first time on television since 1992.

[1] After a lengthy hiatus, a third film, Pee-wee's Big Holiday, was released by Netflix in 2016 and was the last time Reubens portrayed the character before his death in 2023.

In the 1970s, Reubens joined the Los Angeles–based improvisational comedy team the Groundlings and remained a member for six years, working with Bob McClurg, John Paragon, Susan Barnes and Phil Hartman.

The inspiration for the name came from a Pee-wee brand miniature harmonica and the surname of an energetic boy Reubens knew from his youth.

Pee-wee is commonly portrayed as an impatient and fun-loving child with dainty, effeminate mannerisms and quirky facial expressions.

David Letterman once said of the character, "What makes me laugh ... is that it has the external structure of a bratty little precocious kid, but you know it's being controlled by the incubus – the manifestation of evil itself.

Reubens said that he feels Pee-wee "resets" after each adventure, his experiences only changing him slightly, and compared him to Dorothy Gale at the end of The Wizard of Oz.

The show featured the writing and acting of Groundlings alumni Phil Hartman and John Paragon, who would both reprise their characters on Pee-wee's Playhouse.

The Pee-wee Herman Show played for five sellout months at The Roxy Theatre in Los Angeles, whereupon HBO filmed it and aired it as a special on September 11, 1981.

Hartman, Reubens and Michael Varhol co-wrote the script for Pee-wee's Big Adventure, basing the story loosely on Vittorio De Sica's The Bicycle Thief.

[10] Phil Hartman, who would become an SNL cast member the following year, was credited for writing the "Pee-wee Herman Thanksgiving Special" sketch and appeared as a pilgrim in it.

The following year, Pee-wee (along with Hartman) found a home on the small screen with the Saturday morning children's program Pee-wee's Playhouse on the American CBS network for the next five years (Shirley Stoler, Johann Carlo, Gilbert Lewis and Roland Rodriguez appeared only for the first 13 episodes before their characters were dropped or recast).

The show starred Pee-wee living in his wild and wacky Playhouse, full of talking chairs, animals, robots and other puppet and human characters.

[19][20] In reality, the show had been canceled in 1990 due to a combination of multiple complaints of overworked crew members and a feeling that the Pee-wee character had run its course, which ultimately resulted in Reubens deciding against a sixth season.

[21][22] Reubens's fans also organized rallies of support after CBS canceled the scheduled reruns, with several dozens of "Pee-weeites" picketing in Los Angeles, New York and San Francisco.

[16] He remained in a state of shock for weeks and was haunted by the arrest for several years, refusing to give interviews or appear on talk shows.

E. G. Daily (Dotty), Judd Omen (Mickey), Diane Salinger (Simone), Daryl Keith Roach (Chuck, the bike shop owner), and Mark Holton (Francis) were all present.

He first announced he had finished the script on Late Show with David Letterman, and later revealed further details to Time magazine reporter Dennis Van Tine.

[25] During the 2011 Comic-Con in San Diego, Reubens told MTV that he hoped to have Justin Bieber make a cameo appearance toward the end of the movie.

[45][46] While promoting his voice role in The Smurfs 2, Reubens told the Los Angeles Times on the long-gestating project, saying the film has funding, a finished script, and a director lined up.

[49] Paul Reubens confirmed in a January 2009 interview with Swindle magazine that there are indeed negotiations under way for the Pee-wee Herman stage show to return.

The Pee-wee Herman Stage Show: The Return opened on January 12, 2010, at Club Nokia in Los Angeles for a limited four-week schedule.

[61] To promote his Broadway show, Pee-wee Herman guest starred on the November 1, 2010, edition of WWE Raw at the Nassau Coliseum.

[63] Pee-wee Herman returned to WWE at WrestleMania XXVII in a segment with The Rock and Gene Okerlund in which he admitted to being John Cena's number one fan.

[25] In January 2009, Reubens told Gary Panter that the rejected first script of Pee-wee's Big Adventure (which they co-wrote) could have a movie deal very soon, and that it would be "90 minutes of incredible beauty".

This persona, speaking in altered pitch similar to Pee-wee's, persists for the rest of the movie, a stark contrast to Max's original HAL 9000-esque tone.

Shortly after Reubens's 1991 arrest, Jim Carrey impersonated Pee-wee Herman on the FOX sketch comedy series In Living Color.

Later, rapper Eminem imitated Herman in the song "Just Lose It", copying his trademark laugh and even dressing as the character in the music video.

While the Pee-wee Herman character had not originally been intended for a child audience, during the mid-1980s Reubens started forming him into the best role model he possibly could, making of his TV program a morally positive show that cared about issues like racial diversity, the four food groups, and the dangers of making prank calls, but in a manner not overly preachy.