4. Usher (18 awards from 50 nominations)
Usher has shifted much of his focus away from music, but he is still among the best R&B/Hip-Hop artists of all time. His position is firmly sealed by the numerous awards he has won over the years, including the 18 from the Billboard Music Awards.
Usher received his first three awards in 1998 which included the Artist of the Year and R&B/Hip-Hop Artist of the Year awards. His latest BBMA award wins came in 2011 for Top R&B Album thanks to his Raymond v. Raymond album. He has not been nominated in any category since 2013, but that’s not stopping him from making more music.