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Actor and producer Brad Pitt made his big-screen debut in the 1989 horror film Cutting Class and his role in 1994’s Legends of the Fall helped secured his place as a Hollywood staple. A two-time winner of People magazine’s “Sexiest Man Alive” title, Pitt also proved willing to take on grittier roles for features like Seven (1995) and Fight Club (1999). He began earning more serious award consideration for performances in Babel (2006), The Curious Case of Benjamin Button (2008), Inglourious Basterds (2009) and Moneyball (2011), winning his first Oscar in the best picture category as a producer for 12 Years a Slave (2013). Along with later works like The Big Short (2015), Allied (2016) and his Oscar-winning role in Once Upon a Time… in Hollywood (2019), Pitt is known for his high-profile relationships with actresses Jennifer Aniston and Angelina Jolie.