Jeremy Piven is most famous for playing the ball-busting alpha Hollywood agent Ari Gold on HBO’s Entourage, but behind the glitz, the late-blooming Emmy-winning actor is a hard-working craftsman with a diverse career that spans roles in network sitcoms and PBS historical dramas. Kid Cudi is a Grammy-winning multi-platinum rapper who refuses to rest on his laurels, constantly experimenting with his music while also embarking on his own diverse acting career, with roles in projects ranging from teen sex comedies, beloved HBO comedies (RIP How To Make It In America) to intimate, dramatic indies.

While the two are at seemingly different points in their massive careers, that didn’t stop them from bonding on the set of Doug Ellin’s film adaptation of the bro-television classic Entourage, where Cudi plays Ari Gold’s new assistant. Both are clearly artists who will take risks—not letting their previous body of work define them.

The cover stars of Complex’s June/July cover spent time at West Hollywood’s Quixote Studios with Complex’s director of content strategy Joe La Puma, who spoke with Piven and Cudi about the Entourage movie, generational differences, and their working dynamic. JUCO was on hand to photograph the pair, and their natural bond is evident. These are men playing the chess game of the entertainment industry by their own rules.