Nature had designed Lenny Bruce to be the kamikaze of the angry comics. He had an inexhaustible fountain of rage frothing up inside him. He also had the sort of spirit that exults in shaming people, and turning them bottomside up. (p. 184)

Lenny Bruce was a hipster. Lenny stood at the exact focal point of that great myth of the fifties: the Underground Man. In that age of universal conformity, it was believed, there lurked beneath the familiar surface of life an anachronistic underworld of ruthlessly appetitive and amoral beings who achieved heroic intensities through the violence of their rebellion against the middle-class norms. (p. 194)

Lenny aimed to be a real hipster. He hung out with the heavy cats—got right down with them. When he took off some okeydoke spook, he had the sound! He could get his voice up in that high falsetto jive range. Do...