As for Lenny Bruce (Luke Kirby) , a real-life comic and essentially Midge’s mentor, 1960 kicked off his spree of arrests for challenging obscenity laws. In one episode, Abe visits Lenny’s profanity-laced set, which is raided by the police. The two of them are arrested and spend the night in jail. Lenny would later go on to challenge such laws all over the country, using “bad” words to speak out against the Vietnam War, government policies, and racism; sadly, he died of an overdose in 1966