Charles has 17 Grammy Awards to his name, including the five he won in 2005 after his death, giving him the record for most posthumous awards won in a single night.
The comedian won for Best Comedy Recording five times, including his posthumous win for
In addition to the five Grammys she picked up for her breakthrough album Back to Black in 2008, Winehouse won for Best Pop Duo/Group Performance along with Tony Bennett for their "Body and Soul" duet in 2012, the year after her death at age 27.
Out of 14 nominations, the King won only three Grammys during his lifetime. In 2012, he fell short again, when a compilation of his work --
-- lost out to a Paul McCartney archival collection for Best Historical Album.
After he was killed in 1997, Biggie racked up three Grammy nominations for the next year's ceremony -- Best Rap Solo Performance ("Hypnotize"), Best Rap Performance ("Mo Money Mo Problems" with Mase and Puff Daddy ) and Best Rap Album (
) -- but he never earned a single prize.