Will Smith "Men In Black"/"Gettin' Jiggy wit It" (Winner)
George De Sota, Getty
1998 and 1999 Best Rap Performance
Some may complain about DJ Jazzy Jeff and the Fresh Prince winning the first rap Grammy, but I am not among them. Will Smith's early work from "Parents Just Don't Understand" to "Summertime" was pretty great. But he sure as hell didn't deserve a nomination, much less a win, for either of these dreadful solo singles. The former beat Busta Rhymes' "Put Your Hands Where My Eyes Could See," Missy Elliott's "The Rain (Supa Dupa Fly)" and the Notorious B.I.G.'s "Hypnotize," while the latter trumped Jay-Z's "Hard Knock Life (Ghetto Anthem)," Wyclef Jean's "Gone till November" and Lauryn Hill's "Lost Ones." And we all lost a little faith in the Grammys.