Ashton Kutcher & Mila Kunis ($300 Million)

Kutcher is Silicon Valley's most successful celebrity investor. His VC fund A-Grade Investments turned a $30 million fund into $250 million — with early bets on Uber (12x return), Airbnb (before IPO), Spotify, and Warby Parker. Kunis adds $75 million from acting (Bad Moms, Family Guy voice work). Combined: $300 million. They met on That '70s Show and reconnected years later. The actor who played Kelso might have the best investment track record of anyone in Hollywood, which is a sentence nobody expected to write in 2006.