Jay-Z - 19 Grammy Award Wins
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Grammys Hall Of Fame: Which Stars #Own The Iconic Awards Show

2. Jay-Z - 19 Grammy Award Wins
In 2014 Jay-Z upped his Grammys tally to 19 thanks to the award win for Best Rap/Sung Collaboration with 'Holy Grail'. With so many awards back at home with the missus and baby Blue, Jay-Z's a pro when it comes to picking up the gongs, and remains among the artists with the most Grammy wins ever. Not to shabby, eh Hov?