Quincy Jones, 28 In addition to being the living person with the most Grammys, Jones has won Grammys in six consecutive decades -- a distinction he shares with someone else on this list. Jones won his first Grammy at the 1963 awards for arranging Count Basie’s version of the Ray Charles classic “I Can’t Stop Loving You”; his most recent one two years ago for the music doc Quincy. Jones' biggest night at the Grammys was at the 1990 awards, when he won six prizes, including album of the year for Back on the Block. Krauss has, for now at least, won more Grammys than any other woman in the history of the awards. She has won slightly more than half of these Grammys (14) with the ensemble Alison Krauss & Union Station. Krauss, 49, won her first Grammy at the 1990 awards for her album