At 83, Dick Gregory remains an active comedy legend, logging more than 200 stand-up gigs a year. Gregory changed the game in 1961 when he performed at Hugh Hefner’s Playboy Club in Chicago, and the notoriety of becoming the first black comedian to play to white crowds led him soon thereafter to become the first black performer to sit on the couch with Jack Paar when he was host of The Tonight Show on NBC. His 1963 autobiography was a best-seller, and in 1968, he received the fifth-most votes for President of the United States as a write-in candidate. He has remained politically active and topical to this day. Dick Gregory sat down with me in the green room at Carolines on Broadway before going onstage this past weekend, and told me not only about how racism impacted his life and career decisions before comedy, but also how Hefner changed his life, and finally, his thoughts on the passing of Muhammad Ali and the prosecution and persecution of Bill Cosby. Yes, Dick Gregory went there, and his answers may surprise you if you haven’t been paying attention. He’s as thought-provoking as ever.

So let’s get to it!

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