Just as TV had momentarily tamed Lenny, the jazz scene permanently released his inhibitions. He did burlesque gigs with jazz accompanists such as Red Mitchell, Hampton Hawes, Philly Joe Jones, Elmo Hope, Lorraine Geller, and Carl Perkins. Sometimes, as at The Cobblestone in Southern California, he had his own combo with whom he performed: Kenny Drew on the piano; Joe Maini, tenor sax; Herb Geller, alto sax; Lawrence Marable, drums; and Leroy Vinnegar, bass. Jazz's jumble and jive suited him. He liked the "loose," "funky," and "soulful" forms that are the trademarks of jazz, and read about those forms and the jazz lifestyle in Down Beat and Ralph Gleason's Jazz Quarterly. Lenny was so inspired by jazz as an art form that he borrowed much from it for his evolving kind of stand-up comedy. In the clubs, up to one-half or more of his bits were sometimes pitched to the guys in the band—if the audience came along, fine; if not, that was fine, too. He socialized with the jazz set; he loved the jazz life with its alien ethos, its ebb and flow spirit, its menacing eclecticism, its chaotic atmosphere—in short, its freedom.

The nightclubs brought out the hipster, the drug user, and the troublemaker in him. Black music, white powder, and blue comedy mixed to make stage acts that challenged the gods of heaven and earth. It was Cab Calloway, Miles Davis, Charlie Parker, and Little Richard all tumbled into one, verbalized in ways light years beyond the clever imagination of Mort Sahl. "Conveying the particular impact of Bruce," as Nat Hentoff described it, was "almost as difficult as verbalizing about Thelonious Monk, Ornette Coleman or those few other jazzmen who move in a distinctly personal nimbus and who have to be seen and directly felt to be fully believed." You had to hear and see him to believe him, to sense what his live stand-up, shoot-down, blow-up, zig-zag comedy was like. His records, by and large, could only convey a part of the extraordinary dynamic that first made him famous, and then infamous.

At a time when The Nun's Story was debuting in movie theaters and below-the-knee hemlines were popular, Lenny Bruce was busting through the walls of predictability. He was, in his own prophetic words, "chang[ing] the architecture" of comedy in America. Ad-lib and spritzes, combined with unheard-of candor, were the buttresses of that new art form. In the fall of 1959, at the Hungry i in San Francisco, Lenny laid it out autobiographically in his famous, but little performed, twenty-minute bit titled "The Palladium." There, he took aim at the status quo in show business; he "castigated its whoring after status, it preposterous smugness, its crybaby sentimentality, and its secret contempt for the public it fawns." To do that, he hurled comic grenades at the edifices of hypocrisy in the hope of leveling the past and reconstructing the future along the lines of something radically more honest, more human, and more provocative. As the "Palladium" bit reveals, he was quite aware of the personal and professional costs of such provocations. But that would not stop him.

Lenny Bruce was making a case for a new kind of comedy. "[M]y humor is mostly indictment," he explained. And indict he did—with charges leveled against the officialdom of Rome, Hollywood, Washington, Vegas, or any sanctimonious potentate. In a more reflective moment, he added: "I am part of everything I indict." Lenny Bruce, the comic inquisitor, would indict anybody, any institution, or any cause for a (pensive) laugh.

People couldn't believe their ears. He gave public voice to their most guarded thoughts about religion, prejudice, sex, and violence. He violated taboos with murderous impunity. There was never a safe seat in the house, no place for the detached observer to avoid the shock of recognition. "The expectancy in the night club [was always] laced with anxiety," Hentoff stated. "How far will he go tonight?" Rather like an "intimidating panther," observed Arthur Gelb, Bruce prowled and bit sharply, "leaving the stage strewn with carrion."

He loved to walk the fine line, that place forever undefined between the heaven and hell of what is deemed socially acceptable. "Are there any niggers here tonight?" he would ask in the middle of a bit. Shocked silence. Then, the hum of whispers: What was that? Before the people's jaws dropped to their knees, he'd say it again: "Are there any niggers here tonight?" He was making liberals—his defenders—uncomfortable: Does he really have to go that low for laughs? Yes. Because it was all part of a comic campaign to bleed racist words of their poisonous meaning. By bringing the N-word into the open, Lenny filched it from bigots and redefined it on his own we-are-all-created-equal terms. A "strategy of subversion," is how Harvard Law Professor Randall Kennedy tagged it almost four decades later in his book, Nigger. Part of that strategy was to be an equal-opportunity "bigot." Within no time, the bit moved to "kikes, spics, guineas, greaseballs, Yids, Polacks," even the "Irish micks." Bigotry knew no bounds. The result: there was no one left to single out. He thus stunned his listeners into thinking about unthinkable things.

Lenny stalked reality, and then staged it. He invented comic realism: "Let me tell you the truth," he once said. "The truth is what is. And what should be is a fantasy, a terrible, terrible lie someone gave the people long ago." High ideals, mighty truths, or core beliefs: they were shams. Behind the curtain stood a man, not a wizard—a con-man, a hustler who fools himself and others about his should-be world. "We're all hustlers. We're all as honest as we can afford to be," he declared. And so the hustler and his hypocrisy became the butts of Lenny's comedy, the target of his attack on the zug gornischt (say nothing) culture.

One of the prime targets of his relentless indictments was institutionalized religion. Take, for example, his "Christ and Moses" bit. The skit opens with the two holy men standing in the back of St. Patrick's Cathedral; Cardinal Francis Spellman is deep into his sermon. When Archbishop Fulton Sheen interrupts him, Spellman protests: "Stop bugging me." Informed of their heavenly visitors, Spellman panics: "Did Christ bring the family? What's the mother's name? . . . Mary Hail? Hail Mary? Hairy Mary? . . . Oh, Christ, look at the front door. The lepers are coming!" Flesh is falling on the polished floors. Spellman is frantic. He calls Rome: "Hullo, John? Fran, in New York. Listen, a coupla the kids dropped in. . . . Yeah, you know them." Once the pope realizes who the two VIPs are, Spellman explodes: "Well, we've gotta do something. . . . Put 'em up in your place. . . . What am I paying protection for? . . . Look, all I know is that I'm up to my ass in crutches and wheelchairs here! . . . They're in the back, way in the back. . . . Of course, they're white!" All said, Lenny had reduced the Church hierarchy to hucksterism; equality to bigotry; compassion to intolerance. The vernacular became vulgar.

Lenny Bruce: "Christ and Moses"

He was crossing the line. Rude assaults on religion and the Catholic Church would cost him, but not by way of any formal blasphemy charge. What would bring on the heat, what would enable his prosecutions, were those ribald references to "cocksuckers" (San Francisco), "schmuck" (Los Angeles), "tits" (Chicago), and "fucking" (New York). Those junkie-induced shticks—the jazz drummer's riffs on the verb "to come," the unrestrained exposes on "dykes" and "fags," the lurid tale of the Lone Ranger doing Tonto, and Silver, too!—all would contribute to the charge of "obscene Lenny."