1998: Will Smith over Biggie, Missy, and Busta
In the late '90s, the Recording Academy still wasn't quite familiar with what separates a good hip-hop song from a just okay hip-hop song. Perfect proof: In '98 voters chose the safe, familiar, and completely unoffensive (Will Smith's ''Men in Black'') over one all-time-top-10 song (the Notorious B.I.G.'s ''Hypnotize''), a hip-grinding club favorite (Missy Elliot's ''The Rain''), and one of the twitchiest, freakiest beats ever (Busta Rhymes' ''Put Your Hands Where My Eyes Could See''). And by the way, Biggie never won a Grammy.