Really meant to acknowledge Lenny Bruce last month, on the sixtieth anniversary of his death, but the site was offline quite a bit, so kindly accept this belated acknowledgment. That said, in 1961 (when the below "bit" was recorded), dude was probably the only comic whose routines dared to push the envelope about race, class, gender, sexuality, politics, and other topics that were then considered off limits. Moreover, he was arguably the first comedian to use the n-word and profanity in his material -- but only as needed , and/or to make a point. Sadly, Bruce paid a tremendous price for his use of obscenity, and had many entanglements with the law as a result, including a 1964 conviction on obscenity charges, for which he received a posthumous pardon in 2003.
Below, a well intentioned white guy tries to relax his "colored" friend at a dinner party (audio only). __________ note: His daughter, Kitty Bruce, died in May.