Alison Krauss
As of 2018, she has won 27 Grammy Awards from 42 nominations, tying her for the second most awarded recipient alongside Quincy Jones, second only to classical conductor Georg Solti, who holds the record for most wins with 31. She is the most awarded singer and the most awarded female artist in Grammy history.
Chicago Symphony Orchestra
Pierre Boulez, former conductor emeritus and principal guest conductor, won twenty-six Grammy Awards including eight with the Chicago Symphony Orchestra and Chorus. Boulez is the third all-time Grammy winner, behind Sir Georg Solti (thirty-one) and Quincy Jones and Alison Krauss (twenty-seven each). Boulez also received the Academy's 2015 Lifetime Achievement Award.