1. Lenny Bruce
In the 1960s, American comedy experienced a change, and that change was called Lenny Bruce. During a time when mainstream comedy was squeaky clean, Bruce got nasty. His language was so controversial that in 1961, he was arrested under charges of obscenity for using the word “cocksucker” during a stand-up performance in San Francisco. He was acquitted, but his case became a lesson about what one could say in public. It would not be his first arrest.
In 1964, he was publicly arrested under charges of obscenities used during a performance—this time in New York City—and convicted despite testimony from most of the well-known names in Greenwich Village at the time, including Woody Allen, Bob Dylan, and Allen Ginsberg. He was bailed out of his sentence of four months in a workhouse, and eventually his case received a full pardon after his death in 1966.