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.
Grammy Award for Best Comedy Album
Bill Cosby holds the record for most consecutive wins, with six earned between 1965 and 1970. Peter Schickele (of P.D.Q. Bach fame) is the runner-up, with four wins between 1990 and 1993.