9. Madonna featuring Britney Spears, Christina Aguilera & Missy Elliott "Like A Virgin" – On perhaps what was the most iconic MTV Music Awards show performance of all time, Missy Elliott joined the ranks of pops biggest stars. Donning a tuxedo alongside Madonna after the kiss that was heard around the world, Missy made her mark on the pop world by aligning herself as one of the most talented women in music period. Missy went from being one of hip hops heaviest hitters to one of pops most powerful women without having to change who she was, what she looked like or play to anyone’s rules but her own.