Number of times hosted: 1 (1975)
Best skit: “Word Association”

Richard Pryor was the first black man to host Saturday Night Live, back during the show’s first season. The widely admired and unrestrained stand-up comedian boosted the show’s reputation with his performance. The episode he hosted in 1975 (which was also the only time he hosted) features some of the most powerful, memorable sketches the show has ever done, with Pryor acting out an acid trip. SNL famously put the live show on a seven-second delay for this episode, with a censor on-call in case Pryor went off-script and started throwing around any expletives.

His most famous moment, however, was the “Word Association” sketch, in which Pryor is subject to a racially charged word association game in the last round of a job interview. It’s hilarious and shows how talented Pryor was a comedian, pushing the envelope just the right amount.