Scott Brown
August 04, 2000 AT 04:00 AM EDT

He’d been sick all his life, according to his detractors, and on Aug. 3, 1966, dauntless, dirty-mouthed comedian Lenny Bruce succumbed on the bathroom floor of his Hollywood home, a victim of drugs, ”squares,” and his own well-documented knack for self-destruction.

Bruce’s fatal heroin overdose at 40 surprised few but saddened many. For nearly two years, the brazen king of so-called sick comedy had been stuck in a personal and professional nosedive, triggered by his arrest at a Greenwich Village, N.Y., club in the spring of 1964. There was nothing particularly different about Bruce’s act that night — it consisted of the same profane philosophizing he’d been delivering for years, a Molotov cocktail of excoriating social criticism (he was fond of congratulating people for ”leaving the church and going back to God”) and incendiary four-letter epithets.

But this time, the NYPD was in the audience, recording Bruce’s every utterance. On April 4 and again on April 7, he was arrested and charged with obscenity. No stranger to the courtroom, he’d been brought up on similar charges in Chicago and L.A. the previous year (not to mention his busts for narcotics possession). But the Nov. 4, 1964, conviction in New York dealt a serious blow to his livelihood. ”He said, ‘If I can’t work in New York, I can’t work anywhere,”’ recalls Village Voice columnist and free-speech advocate Nat Hentoff. ”His career was over.”

As his finances eroded and police continued to dog him in every city he attempted to play, Bruce, now heavily dependent on heroin, became obsessed with his appeal, even making his court transcripts the centerpiece of his act. ”It was very funny, especially in the context of that very formal, legalistic language, to see words like ‘motherf — -er’ and ‘c — -sucker,”’ remembers Steve Allen, whose variety show gave Bruce a national forum. But Hentoff recalls a less whimsical Lenny, with a hotel room crammed full of legal briefs and First Amendment research. ”He was convinced that he was right,” says Hentoff. ”And he was. But it was too late.”

Eighteen months too late, to be exact. In February 1968, Bruce was vindicated by a state appeals court. His post-humous victory — and cultish martyrdom — spawned plays, movies (including 1974’s Lenny, starring Dustin Hoffman), and even a Broadway musical, and opened the door for the comedy of Richard Pryor, George Carlin, and Chris Rock. Hentoff only wishes Bruce, who relished the slipperiness of language, had lived to see the Clinton administration: ”Can you imagine the riffs Lenny would have done on what ‘is’ is? Oh, what a time he would have had.”

Time Capsule: August 3, 1966
At the movies, Natalie Wood and Robert Redford star in the sex-charged melodrama This Property Is Condemned, directed by a young Sydney Pollack. In music, the Beatles’ ”Yesterday”…And Today is No. 1 on the Billboard LP chart. On stage, with its 2,611th performance, The Fantasticks ties The Threepenny Opera‘s record for Off Broadway longevity. And in the news, financial terms are set on the start of construction of Manhattan’s World Trade Center complex, which, in 1993, was the target of a bombing by Islamic terrorists.

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