Dwayne 'The Rock' Johnson

Dwayne Johnson began as a third-generation professional wrestler in the WWE, where he became one of the most electrifying performers in the history of the business. His wrestling career, spanning from 1996 to his semi-retirement in 2004, generated modest income by today's standards -- but it gave him the platform to become the highest-paid actor in Hollywood and one of the wealthiest athlete-entertainers alive.

Johnson's Teremana Tequila, launched in 2020, sold over 600,000 nine-liter cases in its first year and became one of the fastest-growing spirits brands in history. His equity stake in the brand is estimated to be worth hundreds of millions. ZOA Energy, his energy drink company, and his Project Rock line with Under Armour add further revenue streams. He also earned $20-50 million per film during his peak box office years, with total film earnings exceeding $800 million.

Johnson returned to WWE in 2024 as both a performer and a board member of TKO Group Holdings (the parent company of WWE and UFC), receiving equity that further boosted his net worth. His ability to transition from athletic entertainment to mainstream entertainment to consumer brands makes him arguably the most successful career pivot in sports history.