Ryan Reynolds — Aviation Gin & Mint Mobile

Reynolds bought a stake in Aviation Gin in 2018, personally wrote irreverent ads that went viral, and sold it to Diageo for $610 million in 2020. Then he did the exact same playbook with Mint Mobile — investing, starring in ads, and selling to T-Mobile for $1.35 billion in 2023. His ownership group also bought Wrexham AFC, turning a Welsh fifth-tier football club into a global brand via the FX documentary. Reynolds makes more as a marketing genius than he ever did as Deadpool — and Deadpool made $1.5 billion at the box office.