Lenny Bruce (born Leonard Alfred Schneider) introduced a strongly satirical, taboo-breaking form of comedy during the 1950s and 1960s, which paved the way for some of America’s great comedians — Richard Pryor, George Carlin, Chris Rock, even John Stewart. And for ushering in this new era of comedy, Bruce paid a heavy personal price. In 1961, San Francisco authorities arrested Bruce on obscenity charges. Then, in 1964, Bruce found himself in the crosshairs of Manhattan’s District Attorney, Frank Horgan. A six month trial followed, which raised important First Amendment issues, and which also brought Woody Allen, Bob Dylan, Allen Ginsberg, Norman Mailer, and William Styron to Bruce’s defense. (Dylan would later write a song about the affair.) But, regardless, the trial ended badly for Bruce, and, two years later, the impoverished comedian would die of a heroin overdose.

For Bruce’s legacy, things have gotten a little better. In 2003, Governor George Pataki granted New York’s first posthumous pardon to the satirist, calling it “a declaration of New York’s commitment to upholding the First Amendment.” Meanwhile, legal scholars have written books that paint Bruce and his First Amendment battles in a rather sympathetic light. Below you can find a video clip of Lenny Bruce appearing on the very popular Steve Allen Show. It gives you a pretty good look at the brand of comedy that Bruce presented to the wider nation. (You can access Part II of the video here.) Beyond this, you may also want to check out the actual FBI file that was kept on Bruce. It’s been published thanks to the Freedom of Information Act. And if you’re up for more video footage, here is a clearly deflated Bruce using his trial as fodder for comedy.