In the modern construct of what is commonly referred to as “the culture,” leading purveyors are no less than the contemporary equivalent of Renaissance men. Powerhouse moguls like Pharrell and Diddy, or JAY-Z and Drake, all came in the game off the strength of a specific skill, one they would ultimately transform into multifaceted brands with touch points far beyond their initial artistic contributions. Their legacies are not defined by one hit song, or one clothing line, but rather the conglomeration of consistent success in whichever realm they choose to participate. In most cases, these men have careers that can be broken down into phases, all of which are punctuated by an identifiable moment where they each leveled up.

These are the types of men and stories that will be highlighted in Level Up Your Legacy, presented by Old Spice. Hosted by Rae Holliday, the three-part series will feature a special guest being interviewed while playing a video game based on the guest’s life. The first two levels of the game represent major pillars and achievements currently defining their respective legacies. The third and final level has an eye to the future. What’s next for these trailblazing individuals? How can they level up their legacy?

Circle back to tomorrow to find out, and watch us turn household names, into household games.