2. Garth Brooks (19 awards from 23 nominations)
Garth Brooks has been featured on the Billboard Music Awards from very early on. He won his first two awards in 1991 for Album Artist of the Year and Top Country Album. He proceeded to win five awards in 1992 then three more in 1993. His longest winning streak was from 1997 to 1998 when he won seven awards including the Top Country Artist award in 1998.