Comedian Lenny Bruce gives a victory sign as he leaves a U.S. customs office in New York in 1963 after having been refused entry to Britain “in the public interest.” (John Lindsay / AP)

A version of this essay appeared in the Los Angeles Times.

Wednesday marked the 50th anniversary of the death of controversial comedian Lenny Bruce from an overdose of morphine. His death occurred while his New York obscenity conviction at Café au Go Go was still on appeal, and on the same day he received a foreclosure notice at his Los Angeles home.

But it wasn’t suicide. In the kitchen, a kettle of water was still boiling, and in his office, the electric typewriter was still humming. He had stopped typing in midword: “Conspiracy to interfere with the 4th Amendment const”—constitutes what?

Bruce was a subscriber to my satirical magazine, The Realist, and in 1959 we met for the first time at the funky Hotel America in Times Square. He was amazed that I got away with publishing those profane words for which other periodicals used asterisks or dashes. He had been using euphemisms like “frig” and asked, “Are you telling me this is legal to sell on the newsstands?”

I replied, “The Supreme Court’s definition of obscenity is that it has to be material which appeals to your prurient interest.” He magically produced an unabridged dictionary from the suitcase on his bed and looked up the word “prurient.” He closed the dictionary, clenching his jaw and nodding his head in affirmation of a new discovery. “So,” he observed, “it’s against the law to get you horny.”

When we were about to leave the room, he stood in the doorway. “Did you steal anything?” he asked furtively. I took my watch out of my pocket, since I didn’t like to wear it on my wrist, and without saying a word, I placed it on the bureau. Bruce laughed one loud, staccato “Ha!” and kissed me on the forehead.

We developed a friendship integrated with stand-up comedy. Bruce had broken through traditional, stereotypical jokes about airplane food, nagging wives, Chinese drivers, mothers-in-law. Instead he weaved his taboo-breaking targets—teachers’ low salaries vs. show-business celebs’, religious leaders’ hypocrisy, cruel abortion laws, racial injustice, the double standard between illegal and prescription drugs—into stream-of-consciousness vignettes.

In each succeeding performance, he would sculpt and re-sculpt his concept into a theatrical context, experimenting from show to show like a jazz-jargon musician. Audience laughter would turn into clapping for the creative process itself. “Please don’t applaud,” he requested. “It breaks my rhythm.”

Bruce was intrigued by the implications of an item in The Realist, an actual statement by Adolf Eichmann that he would have been “not only a scoundrel, but a despicable pig” if he hadn’t carried out Hitler’s orders. Bruce wrote a piece for The Realist, “Letter From a Soldier’s Wife”—namely, Mrs. Eichmann—pleading for compassion to spare her husband’s life.

Lenny was writing an autobiography—“How to Talk Dirty and Influence People”—which Playboy planned to serialize, then publish as a book, and Hugh Hefner hired me to edit it. Bruce and I met in Atlantic City, N.J. At a certain point, he was acting paranoid and demanded that I take a lie-detector test. I was paranoid enough to take him literally.

I couldn’t work with him if he didn’t trust me. We got into an argument, and I left. He sent a telegram that sounded like we were on the verge of divorce—“WHY CAN’T IT BE THE WAY IT USED TO BE?” I agreed to try again, and in 1962 I flew to Chicago. Bruce was performing at the Gate of Horn. He was asking the whole audience to take a lie-detector test.

With a German accent, he asked, “Do you people think yourselves better because you burned your enemies at long distance with missiles without ever seeing what you had done to them? Hiroshima auf Wiedersehen [Goodbye Hiroshima].”

“If we would have lost the war, they would have strung Truman up by the balls, Jim. Are you kidding with that? Not what kid told kid told kid. They would just schlep out all those Japanese mutants. ‘Here they did; there they are.’ And Truman said they’d do it again. That’s what they should have the same day as Remember Pearl Harbor. Play them in unison.”Bruce was arrested for obscenity that night. One of the items in the Chicago police report complained: “Then talking about the war he stated, ‘If we would have lost the war, they would have strung Truman up by the balls.’  ” The cops also broke open Bruce’s candy bars, looking for drugs. And the club’s liquor license was suspended.

They checked the IDs of audience members, including George Carlin, who told the cops, “I don’t believe in IDs.” He was arrested for disorderly conduct, dragged along by the seat of his pants and hoisted into the police wagon.

“What are you doing here?” Bruce asked.

“I didn’t want to show them my ID,” Carlin answered.

“You schmuck.”

Because he often talked onstage about his environment, and because police cars and courtrooms had become his environment, the content of Bruce’s performances began to revolve more and more around the inequities of the legal system. “In the Halls of Justice,” he declared, “the only justice is in the halls.” But he also said, “I love the law.”

Instead of an unabridged dictionary, he now carried law books in his suitcase. His room was cluttered with tapes, transcripts, photostats, law journals, legal briefs. In less than two years, Bruce was arrested 15 times. Once, he was teasing his 10-year-old daughter, Kitty, by pretending not to believe what she was telling him. “Daddy,” she said, “you’d believe me if it was on tape.”

Club owners were afraid to book him. He couldn’t get a gig for six months. One Christmas day, he was alone in his hotel room, and I brought him a $500 bill. With a large safety pin, he attached it to his denim jacket. When he finally got a booking in Monterey, Calif., he admitted, “I feel like it’s taking me away from my work.”

Bruce lived way up in the hills. His house was protected by barbed wire and a concrete gate, except that it was always open. He had a wall-to-wall, one-way mirror in his living room, but when the sun was shining, you could see into the room instead of out. He was occasionally hassled by police on his own property. One evening in October 1963, we were talking while he was shaving, when four officers suddenly appeared, loud and obnoxious. He asked them to leave unless they had a search warrant.

One of the cops took out his gun. “Here’s my search warrant,” he said. Then Bruce and the cops had a discussion about the law, such as the rules of evidence, and after half an hour they left. Bruce tried to take it all in stride, but the encounter was depressing, and he changed his mind about going out that night.

When everything was quiet, we went outside and stood at the edge of his unused swimming pool. Dead leaves floated in the water. Bruce cupped his hands to his mouth. “All right, you dogs,” he called out. “Bark for the rich man!”—thereby setting off a chain reaction of barking dogs, a canine chorus echoing through Hollywood Hills.

We ordered some pizza, and he played some old tapes, ranging from a faith healer to patriotic World War II songs. “Good-bye, Mama, I’m off to Yokohama, the Land of Yama-Yama …”

Back at the Café au Go Go, when he was arrested in New York, Lenny had told a fantasy tale about Eleanor Roosevelt, quoting her: “I’ve got the nicest tits that have ever been in this White House …” The top of the police complaint read, “Eleanor Roosevelt and her display of tits.”

At the trial, Bruce acted as his own attorney. He obtained the legislative history of an Albany statute, and he discovered that back in 1931 there had been an amendment proposed that excluded from arrest on an indecent-performance charge stagehands, spectators, musicians and—here was the fulcrum of his defense—actors. The law had been misapplied to him. Despite opposition by the New York Society for the Suppression of Vice, the amendment was finally signed into law by then-Gov. Franklin D. Roosevelt, but to no avail. “Ignoring the mandate of Franklin D. Roosevelt,” Bruce observed, “is a great deal more offensive than saying Eleanor has lovely nay-nays.”

On Oct. 13, 1965 (Bruce’s 40th birthday), instead of surrendering to the authorities in New York, he filed suit at the U.S. District Court in San Francisco to keep out of prison, and he got himself officially declared a pauper. Two months before his death in 1966, Bruce wrote to me: “I’m still working on the bust of the government of New York State.” He included his doodle of Christ nailed to a crucifix, with a speech balloon asking, “Where the hell is the ACLU?”

At a séance, Bruce’s mother brought his old, faded, denim jacket. That large safety pin was still attached to it. And at the funeral, his sound-engineer friend dropped Bruce’s microphone into his grave before the dirt was piled on. Bruce’s problem had been that he wanted to talk onstage with the same freedom that he had in his living room. That problem doesn’t happen to stand-up comedians anymore.

Your support matters…

Independent journalism is under threat and overshadowed by heavily funded mainstream media.

You can help level the playing field. Become a member.

Your tax-deductible contribution keeps us digging beneath the headlines to give you thought-provoking, investigative reporting and analysis that unearths what's really happening- without compromise.

Give today to support our courageous, independent journalists.