When it comes to ballin', Jay-Z is the reigning king. Before it became a trend in hip-hop, Hov was popping champagne bottles on the regular back in the late '90s. In his 'Big Pimpin'' video, Jay-Z and friends, including a shirtless Damon Dash, are on a yacht surrounded by models in bikinis. Joining them on the fun are legendary southern rappers UGK (R.I.P. Pimp C). Big pimpin', indeed.