Has Will Smith ever won a Grammy?
Will Smith has won four Grammy Awards. He won the Grammy Award for Best Rap Performance by a Duo or Group in 1988 for the song "Parents Just Don't Understand" with DJ Jazzy Jeff, the Grammy Award for Best Rap Performance by a Duo or Group in 1989 for the song "I Think I Can Beat Mike Tyson", and the Grammy Award for Best Rap Album in 1998 for the album "Big Willie Style". He won the Grammy Award for Best Rap Performance by a Duo or Group in 1999 for the song "Gettin' Jiggy wit It".