5. Biz Markie — Nike Air Safari

When: 1987

Where: Album Promo

Nobody beats the Biz. Before Biz Markie became one of the biggest sneaker collectors in hip-hop and one of the most sought-after party DJs in the world, he helped introduce the world to the Air Safari, a Tinker Hatfield designed luxury runner that started Nike's shift towards something other than just pure performance. The star of the show is right.