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5. He Won Six Consecutive Grammys

Cosby is one of the best-selling recording artists of all time when it comes to comedy. From 1965 to 1970, he was on a winning streak at the Grammy Awards. He won for Best Comedy Performance and Best Comedy Recording six years in a row, with classic albums like “I Started Out as a Child” and “To Russell, My Brother, Whom I Slept With.” In 1987, he won again for “Those Of You With Or Without Children, You’ll Understand.” Many of his bits focused on childhood, and he was adept at weaving a story with rich detail to set the scene before skewering with a punchline. He’s been nominated 16 times over the years, not just for comedy albums but also work on children’s albums. He has eight gold records and five platinum records to his credit.

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