Whatever his defense lawyers would claim, Lenny Bruce was surely no Jonathan Swift or Francois Rabelais. Rather, what he did in life vacillated wildly between two poles: call them good and evil, moral and nihilistic, pure and dirty, or lawful and lawless. Psychologically, Lenny was torn between the "impulse to be a saint and the temptation to be a criminal." Philosophically, he aspired for the best in humankind (maybe), while he was prepared to accept the worst (definitely). For Nat Hentoff, his friend and defender, Lenny was neither a cynic nor a pessimist. If anything, his philosophy was solipsism—"You don't know anything about anybody but you. Just you live in that thing. You always live alone," is how Bruce once verbalized it. From this singular vantage point, he became increasingly preoccupied with the "elusiveness of any absolute, including absolute truth." Pursuing the big T kind of truth, he believed, gave us not only a false sense of reality, but in time it made us confident in ways that we cannot be, righteous in ways that we could not ever be, and hypocritical in ways that we could never admit to being.

In his everyday life, too, Lenny played out this split-take on living, this unexplainable tension between life as valued and life as lived. "I am heinously guilty of the paradoxes I assail in our society," he readily admitted. Indeed, Don Friedman, his friend and producer, thought as much: "There were two sides to Lenny. On the one hand, he was such a con man. On the other hand, he was human and funny, wanting to reveal lines in the subconscious in order to bring them to the light of consciousness." Though he was torn, Lenny spoke out, mindful of the inconsistencies life imposes. In all of these ways and many others, the comedy of Lenny Bruce was deeply rooted in political, social, and religious commentary. Without them, there could be no Lenny Bruce bits.

To some, Lenny was a comic sage, "a scholar of sleaze," who revealed "the gap between the real and the official." "Un-coded comedy" is what Jack Sobel, his manager, called it. Nat Hentoff described Lenny's technique as a "verbal sleight of hand:" "By stringing together enough Yiddish firecracker jazz jargon" and various other devices, "he reaches his audience with his more serious assaults before they are quite aware that they themselves are also included among his targets." Boldly, Lenny unmasked the masked man; he "delighted in exploring why certain words were forbidden—and then demystifying them," Hentoff added. He challenged "community standards" by questioning whether the community actually held to its Sunday standards. "What I want people to dig," Lenny said, "is the lie." Social conventions of speech sheltered the lies; obscenity, by contrast, outed them; it served up life in its raw and raunchy form. Rebelliously, satirically, and honestly, he took aim—time and again—at the "should" world with vivid reports from the "is" world. "He hated hypocrisy," Harry Kalven Jr.—one of Lenny's lawyers—remarked, "he was almost insanely honest." Lenny put it as only he could: "I'm pissing on the velvet, that's what I'm doing."

Lenny Bruce: "The Lie"

To others, Lenny cut too hard, too close, and too often. "I'm a surgeon with a scalpel for false values," he once quipped. He specialized in humor with an edge, so much so that a London Times obituary claimed that some felt "Bruce sought to disturb rather than amuse." Kenneth Tyson, the London Observer critic, put it this way: "He goes out to do a rush job of psychoanalysis on the audience. He . . . root[s] out their deepest inhibitions, their deepest repressions, all the things they're scared of, the things that are never talked about. And [he] holds them up to the most relentless scrutiny, analyzes them, tries to force the audience to come to terms with reality, actual unspeakable reality." Less charitably, Commonweal reported that Lenny was viewed as a "child who could not accept the careful accommodations of adulthood, the arranged pretenses and self-protective structures of grown-up life . . . ."

Lenny Bruce's work always invited diverse assessments. His fans were unfailing in their dedication to him and his work, no matter how controversial. Conversely, his enemies were unfailing in their antagonism toward him and his work, no matter how commendable. Nat Hentoff captured something of that divided sense in 1963 when he wrote: "After an encounter with Bruce on one of his more demonic nights . . . you may look at the mirror with gnawing doubt that you indeed know who you are, or rather, what you really feel. About sex. About justice. About Negroes. About being a Jew." Demonic . . . gnawing . . . look in the mirror—tough words from an admirer of Lenny Bruce's comedy underscore how it affected his audiences.

His devil-may-care mindset provoked the best, conservatives and liberals alike. Take, for example, the felt need of the American Guild of Variety Artists, the entertainers' union, to reprimand him. While his obscenity prosecutions would surely be seen by Guild artists today as part of the harassment of the arts, back in 1960 that same body of liberal performers tagged Lenny's antics as a "vulgar display of bad taste." In the early 1960s, Lenny once opened a show for the noted singer Mel Torme. During Bruce's performance, as a San Francisco Examiner critic described the incident, Torme turned to a friend and said, "'Who is this disgusting creep? I'm ashamed to be on the same bill with [him].' Bruce overheard just enough, inserting a quick, 'You're ashamed? How do [you think] I feel?'" But the Mel Tormes were not the only ones who took exception to Bruce's comic quips. His bits could even offend the likes of angry hipsters such as Jack Kerouac, who said of Lenny, "I hate him! He hates everything, he hates life!"

However his critics labeled him, Lenny redefined the relations among comedy, the human experience, and the law. When Lenny made private talk public, when he tapped into the taboos, he became prey for prosecutors. Lenny was now uninhibited, robust, and wide-open—wide-open to all sorts of attacks.

The wit, the drama, the irony, the Yiddish nuance (oy vey!), the finger-popping spontaneity were for naught once the vice-hounds got a whiff of those four-letter (and ten-letter) words. Never mind the message: "If God made the body, and the body is dirty, the fault lies with the manufacturer." Never mind the social value of comic commentary: "What's wrong with appealing to the prurient interest? We appeal to thekilling interest." This was sex talk; these were dirty words; it was allobscene.

Lenny was demanding conversational freedom as his constitutional right. His "comedy of dissent" openly proclaimed a "right to be disgusting." The nightclub was the free speech podium where he brought that right to life. But, take free speech to that point, and one thing is certain: the Law will demand its due. As Kalven—a noted First Amendment scholar—observed: "To be as honest as he was, and as perceptive as he was at the same time, was a dangerous combination. . . . In a sense, he was bound to be arrested." Or as Jimmy Breslin put it: he said "bad words . . . in a nightclub and they screamed for the cops." "They" were typically prosecutors, not patrons. It was as though the system had proclaimed: "Cuff him, and don't worry about the fine points—let the courts deal with the constitutional details." That is just about how it went in the cities where he was busted.

No Laughing Matter

THE FUNNY THING about Lenny Bruce is that he was, at times, not funny.

"I wasn't very funny tonight. Sometimes I'm not. I'm not a comedian, I'm Lenny Bruce," he confessed at the close of a San Francisco performance—the one he gave right after his first obscenity bust. By design, his bits were not always funny. That is part of what distinguished him from the comic pack. Funny or not, what Lenny Bruce did on stage defies simple definition. That is why his audiences were uncertain, his critics never quite sure, and his prosecutors often at a loss about what to make of his routines as a matter of law.

The obscenity busts took their toll. They wore him down, trial by trial, dollar by dollar, year after year. Between 1961 and 1966, he gradually became a pathetic caricature of the Time magazine man he once was. From the Nehru to raincoat to denim jacket periods, he took more drugs and more chances. Now, the law was his main routine.

Lenny summoned the proceedings of the courtroom onto the stage, while he tried to do his stage shticks in court. "He lost his sense of reality and no longer knew where he and his art left off and the rest of the world and the law began," observed Edward de Grazia, one of his lawyers. Toward the end, "[h]is bits lost spirit, originality, spontaneity, energy; they became boring, even depressing; often they did not provoke laughter or thought anymore." Well, not entirely.

A surviving video from his August 1965 performance at Basin Street West in San Francisco evidences Lenny's Dostoyevskian obsession with the law and comic madness. Even this late in his life and in the dark dungeon-like atmosphere of the club, one could still sense his comic and satirical greatness, though it came more slowly and not as often now. A badly beaten man, he read from trial transcripts, did truncated and misplaced bits from his famous acts, and capped the show by hustling pedestrians near the offstage door: "Hello, how are you? Dirty Lenny in here. Dirty Lenny is going on soon."

Only a few years earlier, before depression claimed him, he didn't have to barker. He was so much more alive (even "romantic") when he closed an act: "And so, because I love you, fuck you and good night!"