Date: September 4, 1997

The Moment: MTV rolled out one of the most unlikely pairings in the network's history to present the 1997 VMA for Best Dance Video: Martha Stewart and Busta Rhymes, introduced by Chris Rock as "one [who] knows how to make a really mean pot roast, and the other one is always roasted on pot." Martha showed up in muted browns, looking demure. Busta showed up in a red and gold kimono. "What the dilly, yo?" Busta grinned, as Martha Stewart looked both completely uncomfortable and also massively charmed. Martha talked about dropping some beats—or beets—and Busta shouted out Wu-Tang Clan and the Flipmode Squad. The entire thing was, in a word, surreal.

The Impact: It contributed to part a great year for both music videos and the Chris Rock-hosted MTV VMAs, which got high marks from TV and music critics as a high point in the brief history of the network and its awards ceremonies, and more crucially, MTV found itself encouraged to take bigger risks with pairings like Busta and Martha, especially after 1998's Ben Stiller-hosted VMAs failed to thrill in quite the same way. Enter the '99 VMAs, which were hosted again by Chris Rock, but this time, at the Met Opera, and had more than a few watercooler moments, like pairing the mothers of the Notorious B.I.G. and Tupac, or Lil' Kim and Diana Ross, who would jiggle Kim's pasty-covered breast on the VMA stage.

The Upshot: If, in 1997, you were asked who would spend more time in jail over the next fifteen years, you'd probably get this answer wrong. Busta Rhymes remained one of rap's most popular and eccentric acts, and then got very, very in shape, and stopped wearing kimonos, and ceased being weird (and wonderful, to an extent). He never did hard time. Martha Stewart continued to grow her media and kitchenware empire, but did end up going to jail for insider trading. The VMAs fell into decline after the early Aughts, and have yet to reach quite the peak levels of excitement they generated in the late '90s.