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I hate small towns because once you've seen the cannon in the park there’s nothing else to do.
Just a few years after his discharge from the US Navy, Leonard Schneider was arrested in Miami, Florida, for impersonating a priest. He had stolen several priests’ clergy shirts and a clerical collar while posing as a laundry man. He then solicited donations for a leper colony in British Guiana after he legally chartered the “Brother Mathias Foundation”. He was found not guilty due to the legality of the New York state-chartered foundation, the actual existence of the Guiana leper colony, and the inability of the local clergy to expose him as an impostor. He made approximately $8,000, sending $2,500 to the leper colony and keeping the rest.
Soon after changing his last name to Bruce, Lenny earned $12 and a free spaghetti dinner for his first stand-up performance in Brooklyn. From that modest start, he got his first break on the Arthur Godfrey’s Talent Scouts Show, doing Bavarian impressions of American movie stars.
In the time when stand-up comics would come out on stage in a cute little suit and tell cute little mother-in-law jokes, Lenny Bruce was a trailblazer. His routines touched on previously taboo subjects, like moral philosophy, politics, patriotism, religion, law, race, abortion, drugs, the Ku Klux Klan, and Jewishness. His stand-up act featured lines like “If Jesus had been killed twenty years ago, Catholic school children would be wearing little electric chairs around their necks instead of crosses.”  No comedian of that time would dare tread near that type of subject matter. He appeared on the nationally televised Steve Allen Show, where he commented on the recent marriage of Elizabeth Taylor to Eddie Fisher by making his first line an unscripted ‘will Elizabeth Taylor become bar mitzvahed?’
San Francisco columnist Herb Caen was an early and enthusiastic supporter of Lenny, writing in 1959: “They call Lenny Bruce a sick comic, and sick he is. Sick of all the pretentious phoniness of a generation that makes his vicious humor meaningful. He is a rebel, but not without a cause, for there are shirts that need un-stuffing, egos that need deflating.”
In October 1961, Lenny was arrested for obscenity at the Jazz Workshop in San Francisco. He had used the word cocksucker on stage. He was acquitted, but other law enforcement agencies began monitoring his appearances, resulting in frequent arrests under charges of obscenity. The increased scrutiny also led to an arrest in Philadelphia for drug possession in the same year, and again in Los Angeles two years later. By 1963, he had become a target of Manhattan DA, Frank Hogan, who was working closely with Francis Cardinal Spellman, the Archbishop of New York. In April 1964, Lenny appeared twice at the Cafe Au Go Go in Greenwich Village, with undercover police detectives in the audience. On both occasions, he was arrested on obscentiy charges upon leaving the stage. Despite despite positive testimony and support from the likes of Woody Allen, Bob Dylan, Jules Feiffer, Allen Ginsberg, Norman Mailer, William Styron and Dorothy Kilgallen, Lenny was sentenced to four months in the workhouse.
Lenny was arrested 15 times in two years. His performances were banned in Great Britian. At his first show in Sydney, Australia, he got up on stage, declared “What a fucking wonderful audience” and was promptly arrested.
By 1966 he had been blacklisted by nearly every nightclub in the United States, as club owners feared prosecution for obscenity. The less work Lenny got, the more he turned to drugs. His last performance was June 25, 1966, at San Francisco’s Fillmore Auditorium, on a bill with Frank Zappa and The Mothers of Invention. The performance was not remembered fondly by promoter Bill Graham, who described Lenny as “whacked out on amphetamines”.
On August 3, 1966, Lenny was found dead in the bathroom of his Hollywood Hills home. Lenny was lying naked on the floor, a syringe and burned bottle cap nearby, along with various other narcotics paraphernalia. Sportswriter Dick Schaap famously eulogized Lenny in Playboy, with the line: “One last four-letter word for Lenny: Dead. At forty. That’s obscene.”
Lenny Bruce paved the comedic way for George Carlin, Robin Williams, Chris Rock and many others. Thirty-seven years after his death, Lenny was granted a posthumous pardon for his obscenity conviction by New York Governor George Pataki.




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