For the inaugural episode of the Self Made Tastes Better series in 2022, four of hip-hop’s most influential artists—Wiz Khalifa, Rick Ross, Lil Wayne, and DJ Khaled—gathered for a one-of-a-kind conversation. In this unprecedented discussion, the legends opened up about their rise to fame and shared valuable insights from their careers.

The artists reflected on the challenges they faced and the lessons learned throughout their journeys, revealing the pivotal moments that shaped their creative paths. Despite their different stories, all four expressed a shared desire to guide the next generation, offering wisdom on the opportunities ahead and the pitfalls to avoid.

DJ Khaled, with nearly 30 years in the game, reminisced about the vinyl and cassette days, highlighting how hip-hop paved the way for countless artists. During the conversation, Ross and Khaled acknowledged their deep-rooted bond, with Ross praising Khaled’s genuine nature, saying, “You’re authentic,” and emphasizing how that authenticity earns trust, even from the likes of Lil Wayne and Wiz Khalifa. Ross added, “You know how much it would cost to make that call and produce that record today?”

Lil Wayne looked back on his time with Hot Boy$, admitting, “I was way too young to grasp the magnitude of what it could be.” At just eleven or twelve years old, his perspective was confined to his city, and the wider world seemed irrelevant. Wiz Khalifa, the youngest in the group, shared how much he was shaped by the other artists, saying, “I’m a product of all y’all.” He recalled being inspired by Ross during his mixtape days, noting, “When you first started becoming the Boss, I saw that and thought, ‘This is what I want to do.'”