Lenny Bruce may be the most influential stand-up comedian in the history of American comedy. Often cited as an inspiration for the comics that followed in his generation’s footsteps, Bruce’s no-holds-barred satirical style made a lasting impression on the form of stand-up comedy in America (Azlant 2007). In the early 1960s, that style landed Bruce a gig Carnegie Hall, a series of record deals, and recognition by Time as the “the most successful sicknik” – sick comic – of his comic generation (The sickniks 1959). It also landed him in the back of a few police cars, behind bars and, eventually, in the national spotlight at the center of debate about free speech and obscenity in the United States.1