Как давно Уилл Смит начал петь?

Думаю, с детства. :)

Первую Грэмми он получил ровно 30 лет назад:

www.youtube.com/embed/jW3PFC86UNI?wmode=opaque

Другие известные примеры творчества:

www.youtube.com/embed/fiBLgEx6svA?wmode=opaque

www.youtube.com/embed/FYxvPOK6_xg?wmode=opaque

Grammy Awards:

2001Nominee

GrammyBest Short Form Music Video

Will Smith: Will 2K (1999) 

Shared with:

2000Nominee

GrammyBest Rap Solo Performance

Wild Wild West (1999) 

For "Wild, Wild, West"

1999Winner

GrammyBest Rap Solo Performance

For "Gettin' Jiggy Wit It"

1998Winner

GrammyBest Rap Solo Performance

Men in Black (1997) 

for "Men In Black"

1992Winner

GrammyBest Rap Performance by a Duo or Group

Shared with:

For "Summertime"

1991Nominee

GrammyBest Rap Performance by a Duo or Group

Shared with:

For "And In This Corner..."

1990Nominee

GrammyBest Rap Performance by a Duo or Group

Shared with:

For "I Think I Can Beat Mike Tyson"

1988Winner

GrammyBest Rap Performance

Shared with:

For "Parents Just Don't Understand"