Brad Pitt, Gwyneth Paltrow, Oscars Couples

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Brad Pitt is no stranger to the Oscars' guest list. 

A frequent guest of the coveted award show, the Golden Globe winner will be in attendance at the 2020 Oscars and is up for one of the night's biggest honors. On Monday, Brad was nominated for Best Actor in a Supporting Role for Quentin Tarantino's Once Upon a Time in Hollywood, which is up for several awards including Best Picture and Best Original Screenplay. 

But, it's hard to forget Brad's first time at the Oscars. Back in 1996, the Ad Astura star made his Academy Award debut, where he was nominated for Best Actor in A Supporting Role for his performance in Twelve Monkeys. At the time, Brad was dating Gwyneth Paltrow and the couple walked the 68th Annual Academy Awards red carpet arm-in-arm.

Donning tiny oval sunglasses and a sleek suit, Brad looked cool, calm and collected as he made his way down the carpet. For her part, Gwyneth stunned in a sequined Calvin Klein slip dress, which is one of the actress' most glamorous red carpet looks to date. 

The former loves, who met on the set of the crime thriller Se7en back in 1994, got engaged months after the 1996 Oscars but alas, called things off in 1997.

"When two people aren't supposed to be together, they're not supposed to be together," Gwyneth said in 1998. Despite their split, the exes remain friendly, which The Politician star is extremely proud of. "He's a good person," she said during a 2018 interview with The Howard Stern Show.

At the Oscars, Brad ended up losing to Kevin Spacey for his performance in The Usual Suspects, but didn't let the bad news get him down. When the cameras panned to the Inglorious Bastards star, he gave Gwyneth a sweet kiss on the cheek.

But, that wasn't the last time that he made the Oscars' shortlist. In 2009, he earned a Best Actor nom for The Curious Case of Benjamin Button and again for 2012's Moneyball, which was also nominated for Best Picture. But in 2014, he became an Oscar winner when 12 Years A Slave, which he starred in and produced, won Best Picture. His next producing project The Big Short earned him another Best Picture nomination at the 88th Academy Awards two years later. 

Speaking to E!'s Marc Malkin after he and the 12 Years A Slave team got their Oscars, Brad confessed that winning one hadn't occurred to him. "I don't know where I'm going to put it," he said. "I never thought I'd take one home, so I haven't thought that far in advance."

We'll see if history repeats itself at the 91st Academy Awards, which air on February 9. See the complete list of nominees here.

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