Alicia Keys – 15 Wins
There are many artists out there who have to wait decades before they have the honor of winning a Grammy. Alicia Keys was not one of them. The singer-songwriter has won five Grammys in her first shot after her debut album, “Songs in A Minor” earned six nominations in 2002. Today, she’s won 15 Grammys in total and has been nominated 29 times. Somehow, she has yet to win the prestigious album of the year award, but she’s been nominated for it in the past.
Paul McCartney – 18 Wins
Despite the fact that he’s had so much success with Grammy wins, Paul McCartney probably has a distinction he doesn’t want.l Back in 1996, when he was still working with the Beatles, he set the all-time record for most nominations in a night with no wins. He has nine nominations and zero wins. However, he now has won 18 Grammys all the same. His most recent win was in 2014 although he’d been nominated for two Grammys in the rap genre for his collaborations with Kanye West in 2015.