With so many categories, and a lot of the music I love the most not on the recording academy’s radar, the Grammy win that delighted me the most in recent years was Patty Griffin‘s gospel win for her album “Downtown Church” a couple of years ago. That was her first Grammy ever despite years of recording and having her songs sung and recorded by other artists (like Dixie Chicks, Miranda Lambert, Kelly Clarkson). I loved that win.
It took years for the Oscars to finally recognize Kate Winslet. But at the Grammys, she snagged a win the first time in the late 90s. Even Meryl Streep has lost it five times. It’s also pretty great that Betty White has a competitive Grammy.