9. Mariah Carey (14 awards from 20 nominations)
Mariah Carey is one of those timeless musicians who have been rocking the industry since the 80s until now. In all that time, she has neither lost her million-dollar voice nor her good looks. Carey won her first Billboard Music Award in 1991 and received her last BBMA in 2005. WIth songs like Hero, One Sweet Day, and We Belong Together, it’s no wonder she’s won 14 awards from just 20 nominations.