Bruce and his stand-up were largely targeted by police in the early 1960s. He was arrested a whopping five times.
In 1961, the comedian was arrested in San Francisco and later acquitted of obscenity. The following year, he was arrested twice in Los Angeles and once in Chicago on obscenity charges. Only the Chicago charges stood.
In hopes of a pardon, Bruce took his crime to New York City in 1964, where he was summarily attacked by undercover and district attorney investigators who attended two of his performances. Armed with evidence from his crime, the prosecutor convinced a grand jury to charge Bruce with obscenity, which he denied.
When investigators testified using handwritten notes gleaned from Bruce’s act, he said, “I will be judged his bad timing, his Ego, his garbled speech.”
Bruce was sentenced to four months in prison. He later appealed the conviction, but died of a morphine overdose before he could appear in an appeals court.
https://www.latimes.com/entertainment-arts/movies/story/2022-12-12/5-comics-arrested-onstage A brief history of comics being arrested onstage