When and where: 2009, New Jersey Nets press conference

Hip-hop and custom jerseys go hand-in-hand, but this one is different. This one infuses something every rapper brags about, but few can really claim: extreme wealth. Jay-Z's stake in the New Jersey Nets signified a change in the hip-hop culture. While some rappers spent their money on chains and cars, Jay-Z was busy buying NBA teams and moving them to his neighborhood. The jersey wasn't a gift for him to ride around shining with in a video with a vixen girating on his lap. This jersey was an public service announcement everyone had to listen to: Hello, Brooklyn.