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.
Alison Krauss, 27
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 I’ve Got That Old Feeling; her most recent one at the 2011 awards for the Union Station album Paper Airplane. Both won for best bluegrass album. Krauss’ biggest night at the Grammys was at the 2008 awards, when she won in five categories for Raising Sand, a smash collab with Robert Plant.
John Williams, 25
Williams, the most successful film composer of all time, won his first Grammy at the 1975 awards for scoring Jaws; his most recent one was last year for “Star Wars: Galaxy's Edge Symphonic Suite.” Williams, 89, could win his 26th Grammy this year for Star Wars: The Rise Of Skywalker, which is nominated for best score soundtrack for visual media. Williams’ biggest nights at the Grammys were at the 1977 and 1982 awards, when he won three prizes.
Stevie Wonder, 25
Wonder is the only artist in Grammy history to win album of the year with three consecutive studio releases. He swept five Grammys in each of those years (1973, 1974 and 1976). Wonder, 70, won his first Grammys at the 1973 awards, his most recent one at the 2006 awards, when he and Tony Bennett shared the prize for best pop collaboration with vocals for “For Once In My Life,” a song they had each recorded in the 1960s.
Beyoncé won her first two Grammys with Destiny’s Child at the 2000 awards; her most recent one was last year for Homecoming, which won as best music film. She is nominated for nine Grammys (in eight categories) at this year’s awards. Beyoncé’s biggest night at the Grammys (so far) was at the 2009 awards, when she became the first female artist to win six prizes in one night. Beyoncé is 39, making her the youngest member of the 20-plus Grammy club.
Jay-Z has won more Grammys than any other rap star in history. He won for the first time at the 1998 Grammys when his sophomore album, Vol. 2…Hard Knock Life, won best rap album. He won most recently two years ago when The Carters’ Everything Is Love took best urban contemporary album. Jay-Z, 51, is nominated for three awards this year. If he wins them all, this will tie the 2009, 2010 and 2012 awards as his biggest nights at the Grammys.
U2 has won more Grammys than any other group or duo in history. They are also the only group or duo to win album of the year twice. They scored with The Joshua Tree (1987) and How to Dismantle an Atomic Bomb (2005). They won their first Grammys at the 1987 awards, and their most recent ones at the 2005 awards. The 2005 awards, where they won five awards, constituted their biggest night at the Grammys. U2 consists of Bono, 60; Adam Clayton, 60 (he turns 61 the day before the Grammys), The Edge, 59, and Larry Mullen Jr., 59.
Vince Gill, 21
Gill has won more Grammys than any other country artist. He won his first Grammy at the 1990 awards when “When I Call Your Name” won best country vocal performance, male. He won his most recent one at the 2016 awards when The Time Jumpers’ “Kid Sister” won best American roots song. Gill, 63, is nominated this year for best country solo performance for “When My Amy Prays,” a tribute to his wife, Amy Grant. Gill has never won more than two Grammys in any one year.
Kanye West, 21
The rapper and provocateur won his first Grammys at the 2004 awards, and his most recent ones at the 2012 awards. West, 43, is nominated this year for best contemporary Christian music album for Jesus Is King. West has swept four Grammys at two ceremonies -- the 2007 and 2011 awards. Both of those hauls included best rap album -- Graduation and My Beautiful Dark Twisted Fantasy, respectively.
Pat Metheny, 20
Metheny won his first Grammy at the 1982 awards when Pat Metheny Group’s Offramp won best jazz fusion performance, vocal or instrumental. He won his most recent one at the 2012 awards when Pat Metheny Unity Band’s Unity Band won best jazz instrumental album. Metheny, 66, is nominated this year for best arrangement, instruments and vocals for co-arranging his recording of “From This Place,” which features Meshell Ndegeocello. Metheny’s biggest night at the Grammys was the 1998 awards, when he won twice.
Al Schmitt, 20
Schmitt has won more Grammys than any other recording engineer in history. Like Jones, he has won Grammys in six consecutive decades. Schmitt won his first Grammy at the 1962 awards for engineering Henry Mancini’s Hatari soundtrack. He won his most recent one at the 2013 awards as surround mix engineer on Paul McCartney’s Live Kisses, which won for best surround sound album. Schmitt’s biggest night at the Grammys was at the 2004 awards, when he won five prizes for his work on Ray Charles’ final studio album, Genius Loves Company. Schmitt is 90, the oldest member of the 20-plus Grammy club.
Bruce Springsteen, 20
Springsteen won his first Grammy at the 1984 awards (later than you may have figured) for “Dancing in the Dark." Springsteen, 71, won his most recent Grammy at the 2009 awards for “Working on a Dream,” the title track from his then-current album. Both won in rock vocal performance categories. Springsteen’s biggest night at the Grammys was at the 1994 awards when he won four prizes, including song of the year, for “Streets of Philadelphia.”
Billboard Explains: How Grammy Nominees and Winners Are Chosen