Dre’s and Jimmy’s dual ownership of Beats by Dre is an even playing field. Dre has evolved from just being the rapping music producer for World Class Wrecking Crew and N.W.A back in the 80’s and beyond, to becoming hip hop’s first billionaire, after Apple acquired the Beats by Dre brand earlier this year. He is clearly a product of the culture that he’s selling. Jimmy Iovine is not just a music executive, but also co-founder of Beats by Dre. Together they’ve have made sure that both of their respected cultures were firmly represented in the marketing of their brand with artists like Diddy, Lebron James, Serena Williams, Lil Wayne, as well as Lady Gaga, Eminem, Jessie J. and many more.

Flip through the pages to see a gallery of Old School entertainers whom major corporations have worked with to attempt to appeal to an urban audience back in the day.