Both LL and Latifah are former Grammy winners. LL won Best Rap Solo Performance for 1991's "Mama Said Knock You Out" and 1996's "Hey Lover." Latifah won in the same category for 1994's "U.N.I.T.Y." It's interesting that both of the last two hosts started out as rappers, though both are now multi-media stars. Since 2009, LL has been one of the stars of NCIS: Los Angeles. Latifah has appeared in many movies, including Jungle Fever, Hairspray and Chicago, for which she received an Oscar nomination.
Paul Simon, who hosted the show the show in 1981, is true Grammy royalty. He had won 14 Grammys at that point and has since won two more.
Whoopi Goldberg, who hosted the Grammys four times, starting in 1992, had won a Grammy for Best Comedy Recording for her 1985 album Whoopi Goldberg. The album documented her one-woman Broadway show which ran for 156 performances in 1984-1985.
The other Grammy host to win only after his hosting years was John Denver, who hosted six times, starting in 1978. Sadly, his only Grammy win came four months after he died in a 1997 plane crash. That posthumous award came in February 1998 (20 years and two days after he first hosted the show) for Best Musical Album For Children for All Aboard!
All the other Grammy hosts have yet to hear their name called out as a Grammy winner.
Williams' TV stardom was a key factor which enabled producer Pierre Cossette to sell a live Grammy broadcast to television. By 1977, the last year Williams hosted, he was well past his prime as both a TV and recording star, which prompted the shift to Denver, who was then seen as much more contemporary.
The four men who hosted the first 16 live Grammy telecasts were all major recording stars. Simon had won Album of the Year twice (once with Simon & Garfunkel). Williams, Denver and Rogers had all been nominated for that top award. Williams was nominated for 1963's Days Of Wine And Roses; Denver for 1974's Back Home Again and Rogers for 1979's The Gambler.
Four of these hosts (Crystal, Goldberg, Stewart and DeGeneres) subsequently stepped up to hosting the Oscars. You could say that the Grammys were the "host proving ground" for these comics, who have hosted the Oscars a combined total of 16 times (counting Crystal's upcoming return gig).
The oddest choice ever to host the Grammys was Kelsey Grammer, who hosted the 1998 show. Unlike the five previous hosts, Grammer didn't have a background as a stand-up comedian. He was an actor on an Emmy-winning sitcom, Frasier, which was then in its fifth season. No word on whether Grammer whipped up any "tossed salads and scrambled eggs" for the Grammy after-party.
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