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.