Nelly @ Summerfest

Nobody would make the case for Nelly as one of the great rappers, but to fans, he’s symbolic of a better time for pop music, an era when pop-rappers didn’t have to play into EDM trends in order to turn hits. Instead, Nelly won over both pop and rap radio by drawing from popular Southern sounds of the early 2000s. Though he hasn’t released an album since 2013’s M.O., his Neptunes-produced smash “Hot in Herre” remains one of that decade’s great party jams.