The Iconic Rapper Who Owns Multiple Checkers Restaurants

You probably know Rick Ross, the larger-than-life rapper, for his hits like "Hustlin'" and "Aston Martin Music." But while he's known for being a boss in the music industry, he's also known as a savvy businessman in the fast food franchise world. Born William Leonard Roberts II, Ross grew up in Carol City, Florida, a neighborhood in Miami known for its vibrant culture and challenging environment. His experiences growing up there shaped not only his music career, but also his entrepreneurial spirit. In a documentary by UPROXX, Ross describes working at a car wash when he was 13 years old. Across the intersection was a Checkers, the fast food chain with two names (some stores are called Rally's) that serves burgers, hot wings, shakes, and some of the best fast food french fries.

For both Ross and his community, Checkers was the place to gather for affordable food and good times. He describes playing football at his alma mater and running across the street for game fuel. That particular Checkers is his now. "It's the #1 hamburger in the game. The boss said it. The #1 french fries in the game," he says proudly in the documentary, while cruising Carol City streets in his souped-up pickup truck. With a deep personal connection to the brand, Ross' decision to invest in Checkers stems from nostalgic memories of enjoying their burgers and fries during his upbringing in Miami. "Twenty years later, I'm in the financial position where whatever I want to have, I can have it. Without a doubt. I want Checkers."

While his rap career brought him fame and fortune, Rick Ross has always had his eyes set on long-term investments. Ross often speaks passionately about Checkers, emphasizing how the burger brand represents a staple of the community. "This is my favorite spot to go eat, my favorite spot me and my team hung out at," he recalls. "Some of my best memories in the world." By acquiring several franchise locations, he has not only built financial stability but also created employment opportunities and supported the local economy in his hometown. "What made me come back and buy Checker's ... I had a lot of reasons. Providing jobs. Investing back into the community. Staying in touch with where you came from."

Ross' ownership also reflects his belief in economic empowerment and generational wealth, particularly within Black communities. In addition to Checkers, Ross owns dozens of Wingstop franchises, further solidifying his presence in the industry with a top-performing restaurant brand (Wingstop is killing it right now). His dedication to these brands showcases his strategic business acumen and his commitment to supporting accessible, affordable dining experiences. He's also not afraid to have a little fun with his businesses, giving them both a shoutout in his song "Buy Back the Block," featuring 2 Chainz and Gucci Mane. By bringing affordable meals and secure employment to his hometown community, he continues to prove that his boss mentality extends far beyond the recording studio.