By the late 1950s long-held social mores were being challenged on a daily basis. President Dwight D. Eisenhower had sent federal troops to Little Rock, Arkansas, to enforce desegregation in public schools. Elvis Presley transformed the music industry by the highly sexualized and energetic manner in which he performed. The Beat Generation had established a foothold in the cultural landscape. The Beats, who would be akin to today’s hipsters, questioned and/or rejected materialism and values related to love, marriage, family, culture, and politics.

An iconoclastic leader of the Beats was the comic Lenny Bruce, a Long Island–born social satirist who used taboo language and graphic sexual verbiage and imagery in his routine. Bruce’s humor was described as edgy and hip. When he appeared on the nationally televised Steve Allen Show in April 1959, the host described him as “the most shocking comedian of our time—a young man who is skyrocketing to fame.”

Although Bruce behaved himself on television, he was in perpetual conflict with the authorities while traversing the world’s nightclub circuit. He was deported from London and banned from Australia for what was considered to be a blasphemous account of the Crucifixion. He was not allowed to perform in Canada or Detroit. He was arrested for obscenity in San Francisco, Chicago, New York, and Los Angeles, where one of the young city attorneys prosecuting his case was Johnnie Cochran, who would successfully defend O. J. Simpson on double murder charges three decades later. Having also been arrested several times for narcotics possession, Bruce was vilified by many as a foul-mouthed drug addict whose humor had no redeeming quality.

Bruce was vilified by many as a foul-mouthed drug addict whose humor had no redeeming quality.

With the World’s Fair coming to Flushing Meadows–Corona Park in Queens in mid-April 1964, city leaders prepared for the onslaught of international tourists by having the NYPD implement Operation Pornography. Officers converged upon Times Square, arresting smut merchants who were selling anything that might offend puritanical sensibilities. The city enacted a Coffee House Law in an attempt to rein in dissenters who read controversial poetry in Greenwich Village venues. To give the law more sinew, they redefined poetry readings as “entertainment,” which required the locales to operate under the stringent and easily enforceable guidelines of a cabaret license.

On March 31, 1964, three weeks before the commencement of the World’s Fair, Bruce opened at the Café Au Go Go on Bleecker Street. The controversial comic took to the semicircular stage and mused to as many as 350 audience members about his pending court cases, all of which involved either obscenity or drug possession, interspersed with tawdry tidbits that included graphic descriptions of former first ladies.

He commented on Eleanor Roosevelt’s breasts and glibly stated that the iconic photo of Jacqueline Kennedy crawling on the trunk of the convertible seconds after her husband, President John F. Kennedy, was assassinated four months earlier, was not to assist him, but to escape the carnage. She “hauled ass to save her ass,” opined Bruce. “Just what anyone would likely do under the circumstances.”

In a riff Bruce called “Red Hot Enema,” he poked fun at Francis Gary Powers, the CIA pilot whose U-2 spy plane had been shot down over Soviet airspace in May 1960. Powers was interrogated by his KGB captors for months, eventually convicted of espionage, and sentenced to ten years in a Russian gulag. Powers was exchanged for a Soviet spy in February 1962. He did not betray any of America’s military secrets, which led Bruce to say that “putting a funnel up his ass” containing “hot lead” would make him lose his patriotic swagger. In another refrain, “Guys Are Carnal,” Bruce described males as oversexed creatures who would have a one-night stand with anything that moves, including a chicken.

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The sardonic Lenny Bruce is deported from London for a second time. Officials kept him out of the country under the charge of not having a work permit.

Lenny Bruce was arrested shortly before he was to begin a 10:00 P.M. performance at the Café Au Go Go, a Greenwich Village hotspot that catered to the Beat Generation.

In the audience was a cabaret license inspector named Herbert Ruhe, who fastidiously took notes on Bruce’s use of language and masturbatory simulations with the microphone. He described them as “philosophical claptrap on human nature.” A few minutes before Bruce was to begin his ten P.M. show on April 3, he was arrested by the NYPD and booked at the Sixth Precinct on West Tenth Street in the heart of Greenwich Village, presumably the most liberal bastion for artistic freedom in the country.

The case aroused widespread controversy. Scores of prominent academics, literati, and entertainers rallied to Bruce’s defense, describing him as a satirist as relevant as Jonathan Swift and Mark Twain. The six-week trial, which was heard by three judges and no jury, commenced in June 1964 and had to be moved to a larger courtroom to accommodate the throngs of media and observers.

The defense argued that Bruce’s language, while coarse and unconventional, did not inspire the “lustful and lecherous thoughts” that were required by the legal statute. While the defense presented several psychiatric and media experts who testified about Bruce’s social relevance, the prosecutor, Richard Kuh, lamented his difficulties finding experts to counter the defense for fear of being considered squares.

In November 1964, three months after the testimony ended, the judges were set to announce their verdict. Prior to that happening, a bedraggled, desperate, and flat-broke Lenny Bruce dismissed his own attorneys and pleaded with the judges, “Don’t finish me off in show business. Don’t lock up these six thousand words. That’s what you’re doing, taking away my words, locking them up.”

Two of the three judges found Bruce guilty of all charges, explaining that his words were “patently offensive to the average person in the community.” On December 16, Bruce returned to court, where he was sentenced to four months in jail. He remained free pending appeal, during which time the Playboy Press published his autobiography, How to Talk Dirty and Influence People. Although Bruce’s antics would continue to influence people for decades to come, he died of a drug overdose two years later at his Hollywood home on August 3, 1966. He was forty years old.

After Bruce’s untimely death, an assistant district attorney involved in his prosecution expressed remorse for the role he played in the case. “I feel terrible about Bruce,” said Vincent Cuccia. “We drove him into poverty and bankruptcy and then murdered him. I watched him gradually fall apart. It’s the only thing I did in [District Attorney Frank] Hogan’s office that I’m really ashamed of. We all knew what we were doing. We used the law to kill him.”

Decades later, numerous people, including the late comedian Robin Williams, lobbied Republican New York governor George Pataki to posthumously pardon Bruce. In issuing the first such pardon in the state’s history, the staid and conservative Pataki said by doing so it was “a declaration of New York’s commitment to upholding the First Amendment.”