5. Michael Jackson - 'HIStory' Mega Medley (1995)
Just a few months after releasing his career-spanning LP HIStory, Michael Jackson opened up with VMAs with a 15-minute medley of his greatest hits. "Some of us like to play it safe and take each day as it comes," he said midway through. "Some of us like to take that crazy walk on the wild side, so for those of us that like living dangerously, this one's for you." That kicked off "Dangerous," which led into "Smooth Criminal" and a climactic "You Are Not Alone." He didn't appear to be singing everything live, but few people cared. It was still amazing. Later that night, he won Best Dance Video for "Scream." This was one of his last great moments before the downfall.