Smith won his third and fourth Grammy Awards for his work on '' Big Willie Style '' – " Men in Black " won the Grammy Award for Best Rap Solo Performance at the 40th Grammy Awards in February 1998 , and Smith retained the award the following year at the 41st Grammy Awards , when he won for " Gettin ' Jiggy wit It " . At the 26th American Music Awards in January 1999 , he was nominated in the categories of Favorite Pop/Rock Male Artist ( which he lost to Eric Clapton ) and Favorite Soul/R & B Male Artist ( which he won ) , while the album was nominated for Favorite Pop/Rock Album and Favorite Soul/R & B Album , both of which it won . Also in 1999 , Smith received three NAACP Image Awards – Entertainer of the Year , Outstanding Music Video ( for " Just the Two of Us " ) and Outstanding Rap Artist , and was named Favorite Singer at the 1999 Kids ' Choice Awards
26th American Music Awards
American Music Awards of 1999
Big Willie Style