7. Kid Rock feat. Run-D.M.C. and Aerosmith (1999)
In the late Nineties, the seeds of rap-rock that Run-D.M.C. and Aerosmith's "Walk This Way" planted over a decade earlier had grown into several huge multi-platinum acts. And one of them, Kid Rock, was eager to tip a fedora to both in a medley of "King of Rock," "Rock Box" and "Bawitdaba" that culminated, predictably and awesomely, in Steven Tyler and Joe Perry once again bursting through a literal wall to metaphorically break down barriers. Tyler and Kid Rock's mic-tossing routine, catching each other's microphones in mid-air four times with perfect precision, remains one of the VMAs' great showmanship moments.