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On July 26, 1991, Reubens was arrested in Sarasota, Florida for masturbating publicly in an adult theater during a screening of Nurse Nancy. The news media went into a frenzy and the scandal marked the near-death of the character "Pee-wee Herman," reducing both the actor and the persona to a ubiquitous punchline. Although the series Pee-wee's Playhouse had already ended by that time, CBS reacted by dropping its reruns from their lineup. Reubens made a deal with the Sarasota County court: in exchange for a fine and producing a few PSAs, he was given a clean record.

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!"[9][10]

2002

Reubens was arrested again in 2002 in connection with an investigation involving child pornography. Public news stories concerning his case cast doubt upon the suggestion that Reubens intentionally acquired child pornography, as he stated that he was a collector of "erotic artwork" and that he had a sizable collection of vintage erotica with samples dating back to the 18th century. On March 19, 2004, child pornography charges against him were dropped by Los Angeles City Attorney Rocky Delgadillo after Reubens pleaded guilty to a separate "misdemeanor obscenity" charge.

"The DA waited 364 days (one day before the statute of limitations would have run out) and then alleged that some of it was 'child pornography' - decades-old physique poses, old art photos, and yellowed nudist magazines. Some of the nude photos were of minors - when the pictures were taken many years ago. All of the photos, Reubens maintained, were legal when they were first published. The charges were reduced to 'obscenity', and Reubens pleaded guilty and paid a US$100 fine in exchange for probation."[11] Said Reubens:

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