8. Britney Spears' Rolling Stone Cover:While it's hard to imagine today, there was a time when Britney Spears was seen as wholesome and innocent, even despite playing on male fantasies with her Catholic schoolgirl-themed debut video for "Baby One More Time." It was the Lolita-esque April 1999 Rolling Stone cover, featuring the very young pop star lying on a bed wearing little more than a very sexy bra and panties, that first sparked the debate over whether Spears was an appropriate role model for the legions of young girls who worshipped her. The singer would go on to prove that she was, in fact, "not that innocent" with a slew of paparazzi shots of her breasts (and, um, other assets), which seemed hell-bent on escaping whatever article of clothing she happened to be wearing at the time.

7. Lil' Kim's Purple Pasty:It's no secret that MTVs' Video Music Awards are more about the spectacle than the music (a statement that could serve as a slogan for the network in general). We don't remember who performed or what awards went where at the 1999 VMAs, just the way our jaw dropped when the legendary Diana Ross reached out and fondled Lil' Kim's exposed breast with the same level of enthusiasm one might show towards a raw chicken cutlet.