In 1966, Lenny Bruce’s dead body was found. The comedian had overdosed on morphine while naked on the toilet in Los Angeles. It was an ignominious end for a man who had once been the most infamous performer of his day. But by the time he died at 40 years old, had been blacklisted by almost every comedy club in America.

Now, almost 50 years since his death, performers of all types cite Bruce as an influence and inspiration. But he wasn’t just inspiring, Bruce was enabling. He was not simply avant-garde or ahead of his time; Lenny Bruce was a performer who almost singlehandedly ushered in a new era. He challenged audiences, testing their ability to accept new and challenging material. By questioning the status quo, Bruce also challenged the authorities. And the freedoms today’s artists enjoy are in part the result of his bravery and battles.

Lenny Bruce’s act, which included profanity, monologues and stories, even raised constitutional questions, dancing as it did at the edges of the First Amendment. Arrested multiple times, Bruce was the subject of lawyers’ arguments, judges’ and juries’ rulings, and newspapers’ editorials. He became both a star and almost unemployable. Clubs would be fined or have their licenses revoked if they booked him. The Catholic Church, the police and politicians attacked him.

“They said that he was sick ’cause he didn’t play by the rules,” Bob Dylan sang in “Lenny Bruce.” “He just showed the wise men of his day to be nothing more than fools.”

From early in his career, Lenny Bruce said things on stage that no one had ever said before. He broke every taboo. This made him the first modern comedian. But pioneering also came at a heavy price. Bruce was criticized, prosecuted and hounded in the 1950s and 60s for what he enabled others to later do with impunity.

Bruce challenged and transgressed every assumption about what comedy was and what a performer could say. In a noble Jewish tradition, the man born Leonard Schneider questioned everything. But although he posed more questions than even the most eager yeshiva bocher, the closest thing Bruce had to a religion was jazz. He worked with the attitude of a jazzman—riffing, improvising, breaking rules—and employed the language of jazz like “hip” and “dig.”

Bruce was born into a show business family. His mother, Sally Marr, was a dancer, and a comic and stage performer. Often on the road when Lenny was a child, she split from his father, a shoe salesman, when Lenny was still a young boy. Bruce grew up on Long Island, New York, in a culturally Jewish home and was just 16 when he joined the Navy during World War II. He saw active duty in North Africa and Italy. Then after performing in drag for fellow sailors, Bruce left the Navy with a dishonorable discharge having convinced officers that he had gay urges.

Returning to New York, Bruce began performing comedy. He married a stripper named Honey Harlow in 1951, and two years later the couple moved to Los Angeles. They both performed at strip clubs, where Bruce was the house comedian. The couple divorced in 1957 and Bruce’s life would go in another direction when one evening a nightclub owner from San Francisco saw him perform in LA and was impressed. She took him to Northern California, where he met many of the beatnik writers. Laurence Ferlinghetti, the owner of the legendary City Lights bookshop, became a huge fan, as did Jack Kerouac and other writers. Bruce was an artist’s artist, which like “writer’s writer” is a moniker often synonymous with penury. Yet Bruce was gigging.

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He explored meta-humor in which he did not just tell jokes but also made the process of writing and telling jokes his subject. He brought backstage onto the stage. Although it is now easy to see Bruce as ahead of his time, he was in many ways a product of his era—he inspired and fed off beatnik writers and, of course, was even more influenced by jazz.

Jazz provided Bruce with a milieu, an aesthetic and style. He liked everything associated with it–the clothes, the attitude and the lifestyle. Its philosophy of free-flowing association and improvisation resonated with him. He loved to improvise in his act; he felt stifled sticking to script. And his approach seemed to tap into the zeitgeist, for Bruce was on the rise and by 1961 would perform his one-man show at America’s most prestigious venue, Carnegie Hall.

“I have a reputation for being sort of controversial,” Bruce once said onstage. “[…] But you might be interested in how I became offensive.”

Some of his jokes might seem rather tame today (while others remain just as edgy). For instance, one bit for which Bruce was criticized went as follows:

“When people say to me, ‘how are you divorced?’
I always make up a lie and say, ‘my mother-in-law broke up my marriage.’
They say, ‘well how did that happen?’
‘Well one day my wife came home early from work and found us in bed together.'”

This was pretty racy in the late 1950s—as was talking about race, which Bruce also did with regularity. By discussing race, racism and sexuality, Bruce was talking about subjects that he thought important, and that no other performer would touch.

As a result, Time magazine castigated him as a “sick comedian.” It became open season on attacking him.

Bruce got into big trouble for recounting a conversation he had with his agent about a possible gig at a gay bar. In retelling the exchange, Bruce mocked the agent’s use of a homophobic term. But for using the term at all he was prosecuted for obscenity and promoting immorality.

“The bust. What did I get arrested for in San Francisco?” Bruce later recounted on stage. “In San Francisco I got arrested for—I’m not gonna repeat the word because I wanna finish the gig here tonight—[but] they said it was ‘vernacular for a favorite homosexual practice.’”

Bruce had used a term that prosecutors considered an obscenity. And having recently failed in their prosecution of beat poet Allen Ginsberg for obscenity during his performance of “Howl,” the authorities in San Francisco were determined to get Bruce. He was quickly tried and convicted. But his lawyer Al Bendich, who had also represented Ginsberg and worked for the ACLU, found evidence of a technical error by the judge and won Bruce a retrial. This time a jury rather than a judge would hear the case.

The jury agreed with Bruce’s lawyer’s argument that the first amendment entitled Bruce the same freedom of expression onstage as he had at home. They found him not guilty. However, although the jury ruled that Bruce had not committed an illegal offence, they made it known that he was guilty of offending their morals by using such language in public and by discussing subject matter they found uncomfortable. Perhaps true artists disturb people–Bruce certainly did.

Thereafter, police would turn up at his shows, ready to arrest him for any indiscretion. If Bruce knew there were cops present he would often bait them. He was showing off his self-destructive side, sure, but also his bravery and moral courage. Never one to shy away from an argument, Bruce was a fierce critic of organized religion. This, as well as his profanity, drew ire.

The New York County District Attorney Frank Hogan became a sworn enemy of Bruce. A devout Catholic, Hogan believed that Bruce needed to be punished for his attacks on the Catholic Church. So he prosecuted him for his performances in New York City, won his case and Bruce was convicted of obscenity. Police departments in almost every town in which he performed would take an interest in his act. Increasingly Bruce would be prosecuted, and convicted. But believing in his innocence, and that it was the obscenity laws that were criminal in the eyes of the American constitution, Bruce took the fight to the Supreme Court.

In the meantime, the convictions stopped him from being able to perform. And he took more and more drugs. Then he would be tried for drugs, too. Being unable to work was almost a death sentence for Bruce. His inability to perform and mounting legal fees forced him into bankruptcy.

The culmination was his death on August 3, 1966.

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“America’s foremost, and certainly most truthful, philosopher died from an overdose of police,” Phil Spector wrote in an ad he published in Billboard magazine after the event. For despite his convictions and blacklisting, Bruce was also much loved. Even in his own lifetime he was compared to Swift and Aristophanes. Many saw him as an artist prosecuted for transgressing morals in the tradition of D.H. Lawrence and Henry Miller.

Bruce’s trial was considered a landmark in the fight to preserve the freedoms set forth in the US Constitution’s First Amendment. “Lenny Bruce’s legacy is freedom of speech and telling it as it is, getting your life and putting it out on the table, telling everyone about it,” said British comedian Eddie Izzard.

Two years after he died, the Supreme Court ruled as Bruce had hoped: they reversed his conviction and formally dismissed all outstanding charges against him. Almost 40 years later, in 2003, Governor of New York George Pataki gave Bruce the state’s first posthumous pardon.

But these legal victories came too late for Bruce, who was perhaps only guilty of coming too soon. Perhaps, as Bruce once said, “Life is a four-letter word.” Or maybe his obituary in Playboy, written by Dick Schaap, put it best with, “One last four-letter word for Lenny: Dead. At 40. That’s obscene.”

Top Lenny Bruce famous quotes:

“Every day people are straying away from the church and going back to God.”

“The ‘what should be’ never did exist, but people keep trying to live up to it. There is no ‘what should be,’ there is only what is.”

“The role of a comedian is to make the audience laugh, at a minimum of once every fifteen seconds.”

“There are never enough ‘I love you’s.’”

“If you live in New York, even if you’re Catholic, you’re Jewish”

“Life is a four-letter word.”

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