50 Pop-Culture Moments That Rocked Fashion: The Top 25

Notorious B.I.G. (featuring Mase, Puff Daddy)

Gangsta rapper appropriates gay anthem to create a bouncy behemoth as shiny as the costumes in its video. ''Ten years from now we'll still be on top''? True — every time we hear this song.

SHIRTS AND SKIN A 16-year-old Britney instantly gained millions of teen (and dirty-old-man) fans with the naughty-schoolgirl video for her 1998 debut single ''...Baby One More Time.''

Like a virgin? Not quite. When the burgeoning pop singer formerly known as Ms. Ciccone hit the stage in a lingerie-like wedding dress, fingerless gloves, and multiple crucifixes — the first of many signature looks — a star was born. Her bold tweaking of sexual mores may seem commonplace now, but to a nation of young women, it was a revelation.