Brad Pitt Thought Starring in a Movie with Girlfriend Juliette Lewis Would Be Like a Vacation

Who: Oscar and Emmy-nominated actress and singer Juliette Lewis, 45, and Oscar and Emmy-winning actor and producer Brad Pitt, 55.

How They Met: Lewis and Pitt met on the set of TV movie Too Young to Die? (1990) but didn’t begin their romance until the film wrapped. (Lewis was about 17 when they began dating, and Pitt was 27.) They reunited for Kalifornia (1993) and were thrilled to be working together. “We're like at the point in love, where we just like to see each other every single day and we don't get bored with each other, so it's really, really nice,” Lewis told the L.A. Times in ’93.

Pitt, too, was excited to “do a scene and then go over and grab the one you love.” He told the publication, “You want to keep your careers your careers and your love your love, but we just wanted to do it more for a vacation." They split three months after this interview was published.

Why We Loved Them: This was a (figurative) marriage of true up and comers. When they first met, Lewis was best known for a four-episode arc on The Wonder Years, and Pitt for guest-starring on Dallas. By the time they split, Lewis had an Oscar nomination for Cape Fear and Pitt’s abs had captured America’s full attention in Thelma & Louise.

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“It was such a lovely time in my life — well, in both of our lives — because we were anonymous. For half of our relationship we were just unknown young actors in L.A.,” Lewis told BlackBook in 2009. “I even remember his little bungalow that we lived in off Melrose that we’d smoke lots of pot in,” she added.

For better or worse, they rose to fame together, and there’s something poetic about that, no?

When They Peaked: The 1992 Academy Awards, 1,000 times over. This being an early ‘90s relationship, their red carpet fashion was memorable, but no occasion more so than the Oscars, to which Lewis wore a glittering ivory ‘20s-style gown, satin gloves, a hip-grazing string of pearls, massive gem-encrusted stud earrings, and — wait for it — cornrows. It was 1992, so there probably wasn’t a Kim Kardashian wearing “Bo Derek braids”-level backlash at the time, but the style definitely hasn’t aged well.

Pitt, on the other hand (who has aged incredibly well), wasn’t problematic with his Oscars style, but his look did end up being something of a head-scratcher — red carpet ascot, two-tone wingtip oxfords … OK!

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Looking back at photos from their time together decades later, Lewis admitted to occasionally wearing Pitt’s clothes. "This is what I love about old photos. I was wearing his shirt and some random pants from my closet,” she said. “I love that there was no styling.”

The Breakup: After living together for three years and starring in two films together, Lewis and Pitt called it quits in early 1993. Juliette’s publicist said they planned on “remaining friends.” Not much else was made public, but Pitt weighed in on the relationship in 1994, telling Rolling Stone, “We were trying to be Sid and Nancy or something. We were idiots. We were just having a great time.”

In 1995 he gave Vanity Fair a closer look, explaining, “I still love the woman. There’s some real genius there. I had a great time with her.” He continued, “Look, I don’t want to go into an explanation. She has her own views, and I respected those views. She does know people. It was one of the greatest relationships I’ve ever been in. The problem is, we grow up with this vision that love conquers all, and that’s just not so, is it?” Deep, Brad. Deep.

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Brad’s references to those “views” of Juliette’s may refer to her lifelong devotion to Scientology. He reportedly took two courses in the church while they were dating but didn’t follow up after their split.

Lewis, for her part, remembers the relationship fondly. “He's a stand-up guy from Missouri, really honest and decent,” she told The Guardian nearly two decades after their split. That being said, they don’t exactly hang. "He's not in my universe at all now," she explained. "It seems like a high-school relationship because now he's a very famous person. I look at this person that I shared a bit of history with. I hope he finds happiness because I genuinely loved him. He's a very stand-up, good guy. Four years was an eternity at that time. It was my longest relationship and we both lost our anonymity together. Huge life changes all occurred, all connected to that person."

Where They Are Now: Pitt really built his A-list romance resume after his split from Lewis. He got engaged to Gwyneth Paltrow in 1996 (though they broke things off seven months later), wed Jennifer Aniston in 2001, divorced the Friends alum in 2005, began dating Angelina Jolie, became a father of six, married Jolie in 2014, and filed for divorce in 2016. He’s reportedly been dating in the years since, but no partners have been confirmed.

The actor rose to Hollywood’s highest echelon following his relationship with Lewis. He went on to star in Se7en, Ocean’s Eleven, The Curious Case of Benjamin Button, and about a bazillion other major films of the late 20th and early 21st centuries.

Most of Pitt’s recent work has been behind the scenes — he won his first Oscar as a producer for 12 Years a Slave in 2014. But the actor’s latest starring role is in one of his buzziest projects to date: Quentin Tarantino’s Once Upon a Time in Hollywood, out this July. Later this year, Pitt will appear in outer space drama Ad Astra.

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Lewis wed pro skateboarder Joe Berra in 1999, but she filed for divorce just four years later in 2003. She went on to date Gym Class heroes frontman Travie McCoy, and has been linked to Rage Against the Machine drummer Brad Wilk since 2016.

Lewis delivered a string of critically acclaimed performances throughout the nineties and early-aughts before she turned her focus to music in 2003. She led rock band Juliette and the Licks until its split in 2009, after which she went solo. She recently starring in HBO’s Camping and can be seen next in psychological thriller Ma alongside Octavia Spencer, out May 31.