During the turbulent 1960s, Gregory became a pioneer in stand-up comedy for his "no-holds-barred" sets, in which he mocked bigotry and racism. He performed primarily to black audiences at segregated clubs until 1961, when he became the first black comedian to successfully cross over to white audiences, appearing on television and putting out comedy record albums. Gregory was at the forefront of political activism in the 1960s, when he protested the Vietnam War and racial injustice. He was arrested multiple times and went on many hunger strikes. He later became a speaker and author, primarily promoting spirituality.