Diddy

Net worth: $600 million (previously estimated at $1 billion before legal troubles in 2024). Sean Combs built Bad Boy Records, Sean John fashion, Ciroc Vodka (a partnership with Diageo worth $60 million per year), and DeLeon Tequila. He won three Grammys and produced iconic albums for Biggie, Mary J. Blige, and others. However, his net worth estimates dropped significantly in 2024 following multiple lawsuits and federal investigations. His business empire remains substantial but his legacy is now complicated by legal proceedings that were ongoing as of 2026.