During winters, the Ringling Bros. and Barnum & Bailey Circus called Sarasota home, and young Paul counted such big-top families as the Wallendas and the Acchinis among his neighbors. The circus sparked his interest in entertainment.
Reubens attended Sarasota High School, where he was named president of the National Thespian Society. He also joined the local Asolo Theater and Players of Sarasota Theater, appearing in a variety of plays.. After graduating he attended Boston University for one year before deciding to seek his fortune as Paul Reubens in Hollywood. There, he enrolled as an acting major at the California Institute of the Arts and accepted a string of pay-the-rent jobs ranging from pizza chef to Fuller Brush salesman.
In the 1970s, Reubens performed at local comedy clubs and made four guest appearances on The Gong Show as part of a boy-girl act. He soon 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. Hartman and Reubens became friends, often writing and working on material together.
Reubens auditioned for Saturday Night Live for the 1980-1981 season, but Gilbert Gottfried got the place. Reubens was so angry and bitter that he decided he would borrow money and start his own show in Los Angeles using the character he had been developing during the last few years, "Pee-Wee Herman".
After acquiring a small group of followers, Reubens took his show to The Roxy Theatre where "The Pee-Wee Herman Show" runned for five sellout months, going into the mainstream with the successful 1981 HBO special The Pee-wee Herman Show. Reubens act had mainly positive reactions and quickly acquired a group of fans, despite being called by critics "naturally puny", and Reubens being described as "the weirdest comedian around". Pee-Wee was both "corny" and "hip", "retrograde" and "avant-garde".
When "Pee-Wee"'s fame started growing, Reubens started to move away from the spotlight, keeping his name under wraps and making all his public appearance and interviews in character while billing Pee-Wee as playing himself; Reubens was trying to "get the public to think that that was a real person". In the early and mid 1980s Reubens made several guest appearances on Late Night with David Letterman as Pee-wee Herman. These performances gave Pee-wee an even bigger following than he had with his HBO special. During the mid 1980s Reubens traveled the United States with a whole new The Pee-wee Herman Show, playing notably at the Guthrie Theater in Minneapolis, Caroline's in New York City and, in 1984, in front of a full Carnegie Hall.
Reubens went on to say that it was his appearances on David Letterman's show that made Pee-wee a star.
Playhouse was designed as an educational yet entertaining show for children, being greatly influenced by 1950s shows Reubens watched as a child like The Rocky and Bullwinkle Show, The Mickey Mouse Club, Captain Kangaroo and Howdy Doody, Playhouse quickly acquired a dual audience of kids and grownups. Reubens was also after making a significantly moral show, one that would teach children the ethics of reciprocity. He was always conscious of the importance of having an ethnically diverse cast. Reubens believed that children liked the Playhouse because it was fast-paced, colorful and "never talked them down"; while parents liked the Playhouse because it reminded them of the past.
Playhouses premise was host Pee-wee Herman living in a wild and wacky house, known as the Playhouse, full of talking furniture, animals, robots, and other puppet and human characters. Each episode usually contained a running gag particular to that episode, and/or a specific occasion that would send Pee-wee into an emotional frenzy. The show had many recurring gags, themes, and devices, for example at the beginning of each show, viewers were told the day's "secret word" and were instructed to "scream real loud" every time a character on the show said the word. Despite being a live action show there were lots of puppet and clay animation sequences, some of them made by Peter Lord and Nick Park, creators of Wallace & Gromit. Occasionally brief clips from the 1930s, the Golden Age, would appear, usually presented by the "King of Cartoons".
The show aired from September 13, 1986 until November 10, 1990. Reubens had originally agreed to do two more seasons after the third, and when CBS asked Reubens about the possibility of a sixth season he declined, wanting to take a couple of sabbatical years. Both parties mutually agreed to end the show after five season, which included 45 episodes and a Christmas Special. Playhouse garnered 22 Emmy Awards, most of them in the Creative Arts Emmy Award category.
In 1987, he provided the voice of REX, the bumbling pilot droid in the Disneyland attraction, Star Tours, and reprised the role of Pee-wee Herman in a cameo appearances in the film Back to the Beach and TV show Sesame Street. In 1988, Reubens reprised the role of Pee-wee Herman in a sequel to Pee-wee's Big Adventure, entitled Big Top Pee-wee. Also that year, "Pee-wee" was awarded a star on the Hollywood Walk of Fame.
In early July 2006, Cartoon Network began running a promo during its Adult Swim lineup. The promo consisted of a black screen with the text, "Remember This?" displayed, while the beginning of the Pee-wee's Playhouse theme song played in the background. The commercial then faded to the text "Coming July 10, 2006." A later press release and many other promos confirmed that the show's 45 original episodes would air on the block Monday to Thursday at 11 P.M. ET starting on that date. However, later on in August 2006, Adult Swim started airing Pee-wee's Playhouse at 12:00 A.M. ET.
On Saturday, August 5, 2007 at a showing of Pee-wee's Big Adventure in the Hollywood Forever Cemetery in Hollywood, CA, Reubens made an appearance on stage before the show, bringing with him almost the entire cast of the film to the uproarious applause and standing ovation. 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.
In October 2006, Reubens made a rare public appearance at an east-coast fan convention, "Chiller Theater," with "Pee-wee's Playhouse" co-star, Lynne Marie Stewart. There he donned a gray suit with a bold red necktie, and signed autographed pictures and other memorabilia-- along with posing for photographs with fans.
In early 2007 Nike SB released a style of Nike SB sneakers, Grey/Heather Dunk High Pro SB, that use a grey and white color scheme with red detail inspired by the colors of Pee-wee Herman's trademark suit and an illustration on the insole suggesting Reubens' theater arrest. No explicit reference is made to the inspiration as they are unauthorized. They are part of a "Fallen Heroes" pack which also features shoes inspired by Milli Vanilli, MC Hammer, and Vanilla Ice.
Despite the negative publicity and backlash from CBS, many spoke out in support of Reubens. Bill Cosby defended Reubens, saying "Whatever (Reubens has) done, this is being blown all out of proportion." Reubens' fans also organized rallies of support. According to Entertainment Weekly, "several dozen vocal Pee-weeites picketed in L.A. and New York [a week later], and 250 demonstrated in San Francisco the following day." Supportive fans chanted, "All we are saying is give Pee-wee a chance! It was much implied at the time that he had gotten arrested on purpose to "get out from under the Pee-Wee character", allegations Reubens has dismissed many times as ridiculous: "That’s like saying Lana Clarkson shot herself in the face.” (Which is what Phil Spector, the record producer, on trial for her murder, says she did in 2003.)
In November 2001, while he was filming David La Chapelle's video for Elton John's This Train Don' Stop There Anymore Reubens learned that policeman were at his house with a search warrant, acting on a tip from a witness in the pornography case against Jeffrey Jones. founding among kitsch memorabilia what the city attorney's office characterized as a collection of child pornography.
Reubens turned himself to the Hollywood Division of the LAPD on Novemeber 15, 2002 and was charged with misdemeanor possession of obscene material improperly depicting a child under the age of 18 in sexual conduct. He was released on $20,000 bail and could at the time face a maximum sentence of one year in prison and a $2,500 fine.
Reubens was represented by Hollywood criminal defender lawyer Blair Berk, who has also represented geneticist and convicted felon William French Anderson, actor Mel Gibson, actress Lindsay Lohan and other celebrities. On December 13, 2002 Reubens pleaded innocent through Berk, who from the beginning seeked to have the charges thrown out. She also complained to court Commissioner that the city attorney's office hadn't turned over its evidence to the defense, which City Attorney Richard Katz countered that prosecutors were not required to do so until after the arraignment, after which they did, although neither side disclosed the contents of the documents.
On March 19, 2004, child pornography charges against him were dropped by Los Angeles City Attorney Rocky Delgadillo after Reubens pleaded guilty to possessing obscene images of minors so as to avoid going to court and risking jail. For the next three years Reubens had to register his address with the sheriff's office and could not be in the company of minors without their parents' permission.
Reubens later stated that he was a collector of "erotic artwork", a collection that includes films, muscle magazines and a sizeable collection of vintage erotica, such as photographic studies of teen nudes. Reubens claimed that what the city attorney's office viewed as pornography, he considered innocent art and that what they described as people underage engaged in masturbation or oral copulation was in fact a judgemental point of view of the nudes which Reubens described as people "one hundred percent not" performing sexual acts.
Personally, I think we're living in a very scary time. Do we let the legal system decide in a courtroom what's obscene and what's not obscene?(...) One thing I want to make very, very clear, I don't want anyone for one second to think that I am titillated by images of children. It's not me. You can say lots of things about me. And you might. The public may think I'm weird. They may think I'm crazy or anything that anyone wants to think about me. That's all fine. As long as one of the things you're not thinking about me is that I'm a pedophile. Because that's not true.
Prior to his arrest, Reubens had made a guest appearance on the hit TV series Everybody Loves Raymond, playing the role of Amy McDougall's comic-book-obsessed brother (Russel McDougall). His arrest prompted the show's star, Ray Romano, to object to Reubens being a part of the show's cast and actor Chris Elliott was cast as the character of Peter McDougall, apparently a second brother of Amy's, to replace Reubens' role.
On July 30, 2006, Reubens played Rick of the citizen's patrol on the popular Comedy Central show Reno 911!. The character, Rick, wore a red beret with numerous pins on it, a pair of white gloves, and a small cape. Rick always found clues and evidence that the officers would have otherwise never found, usually making them look very novice. He spoke with a scratchy whisper throughout the entire episode until near the end when officer Dangle plays a voice recorder where Rick is making chicken noises and laughs like Pee-wee Herman.
Reubens played a prince on the 30 Rock episode "Black Tie", which aired on February 1, 2007. Paul Reubens played a veteran journalist on the FX series "Dirt". The episodes were titled "The Secret Lives of Altar Girls" (aired Feb. 6, 2007) and "Come Together" (aired Feb. 13, 2007). On February 25th, 2007, Reubens made an appearance on the Tim and Eric Awesome Show, Great Job! as the moon in the closing segment of the episode "Cats". Reubens makes a cameo in Reno 911!: Miami as Terry's dad. Reubens appears in The Tripper with David Arquette and Courteney Cox. It was released April 20, 2007. Starting May 2, 2007, Paul Reubens reprised his role as Golly Gopher in the television series based on Re-Animated. He has a recurring role on Chowder as the voice of the character Reuben. Paul has made an appearance on The Andy Milonakis Show in season 3, as "Weird Beard the Weirdly Bearded Weirdsman." He also provided the voice for the character Paul, in the episode "Puddins" of "Tom Goes to the Mayor".
Reubens appeared as the Pee-wee Herman character for the first time since 1992 at Spike TV's 2007 Guys' Choice Awards in June 2007.
Reubens was slated to appear as homeopathic antidepressant salesman Alfredo Aldarisio in the third episode of Pushing Daisies. The role was recast with Raúl Esparza. Reubens instead appeared in the role of Oscar Vibenius in the series' 7th and 9th episodes.
Reubens' third scripted movie, written at the same time as his adult-oriented Pee-wee script, was announced in late summer 2006. He first announced he had finished the script on the Late Show with David Letterman, and later revealed further details to Time reporter Dennis Van Tine. Filming was expected to start in early 2007. According to IMDb, it is expected for a release in 2009 because of delays with the writer's strike. It is also known that Paul Reubens currently made three scripts relating to this latest film. In a 2004 interview with Entertainment Weekly, Reubens said that he was working on a few television and movie ideas, and that Hollywood, he hoped, had not seen the last of Reubens or his alter ego, Pee-wee. Reubens has also stated a strong possibility of a Pee-wee's Playhouse movie on an NPR interview with Terry Gross on December 27, 2004. A third Pee-wee movie was also suggested. Both, said Reubens, are actively being worked on, but no dates or official announcements were made as of this date. On July 11, 2006, Reubens made a rare talk show appearance to promote Pee-wee's Playhouse on the Late Show with David Letterman, and made mention that a script was completed for a Pee-wee's Playhouse Movie which would take the characters from the 1980s television show out of the playhouse for the first time and into the real world. In a Time interview, Reubens said production would start early next year for the film.