"Jiggy" is a term meaning to be cool and trendy. It's often associated with a style of dress, and in the context of this song means dancing effectively and also making a name for yourself. It also became a term for sex.
The song won a Grammy Award in 1999 for the Best Rap Solo Performance. It was ranked the 68th greatest song of the 1990s by VH1. However, it was ranked at #19 on the list of AOL Radio's 100 Worst Songs Ever in 2010. The song was included in Pitchfork Media's 2010 list of "the seven worst U.S. No. 1 singles of the 90s".
