It’s only right to have this rapper as one of the best Grammy winners of all time. He won his first Grammy back in 1992 for Best Rap Solo Performance for the hit single, “Mama Said Knock You Out.” He is one of the first rappers to win this award and he ended up winning in the same category for the hit single, “Hey Lover” featuring Boyz II Men. Since winning his two Grammy Awards, he kept busy throughout the years with his music and movies. He became a mini mogul in his own right by releasing exercise books and launched a clothing line called Todd Smith. And oh yeah, he’s hosting the Grammy Awards this year!