Pitt has been nominated at the Oscars seven times . He won once in 2014, taking home a trophy for Best Picture as a producer for 12 Years A Slave. That’s arguably how he’s making most of his money in Hollywood nowadays. Pitt founded his production company, Plan B Entertainment, with his now-ex-wife Jennifer Aniston in 2001 (he bought out her stake in the company when they split up). Plan B has backed heavyweight films including The Departed, Moneyball, Moonlight, and The Big Sick, not to mention box office hits including Charlie and the Chocolate Factory and Eat, Pray, Love. Plan B currently has deals inked with Annapurna Pictures and Amazon Studios, Deadline reports, so there’s little question that Pitt’s role as a producer is likely one of his highest-paying yet.