Brad Pitt, Ines de Ramon Make Rare Red Carpet Appearance Together

Pitt scored an appearance on the Riverdale actress' sitcom Head of the Class in January 1989. The ink on Givens' divorce from Mike Tyson wouldn't be dry until that February, however, and the boxing champ later recalled seeing Pitt toking away when he came across him at his estranged wife's house one morning—where Tyson says his intent was to have a quickie while on his way to see his divorce lawyer.

"She drives up with the handsome Brad Pitt," he said while telling the story, then a sample anecdote from his one-man show, on Conan in 2012. "I said, 'aw man, I ain't gonna get no p--sy, f--k.'" Andy Richter chimed in, "Brad Pitt is the international symbol for that."

The tale continued to be a favorite for interviewers over the years, with Tyson concluding on The Real in 2016, "I didn't really catch them in the act—maybe before the act...He's a really nice guy."

Pitt rocked Davis' world onscreen as a hustling hitchhiker in 1991's Thelma & Louise, which proved to be the actor's (and his abs') true breakout role—and Pitt's onetime roommate Jason Priestley claimed in his 2014 memoir that they were an off-screen item as well. 

"I actually read with him first—there were five candidates for the role," Davis recalled Pitt's audition to The Hollywood Reporter in 2014. "And then he came in—this is so embarrassing—but I got a little distracted during the scene, you know? I was forgetting my lines. I was like, 'I'm totally screwing up this kid's audition.'"

These two played murderously dysfunctional couples twice, in the 1990 TV movie Too Young to Die? and the gritty 1993 thriller Kalifornia, but real life seems to have been sweeter during the several years—he was her Oscars date in 1992 when she was nominated for Cape Fear—they were together.

"I still love the woman," Pitt told Vanity Fair in February 1995. "There's some real genius there. I had a great time with her...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?" In 2010 Lewis told Pop Tarts that she and Pitt "run into each other on and off and we say hello and that is really nice."

Thandiwe Newton

Pitt has described his experience making Interview With the Vampire as "miserable." He told Entertainment Weekly in 2011 that "the great thing that came out of that movie is that it birthed my love affair with New Orleans." 

But the shoot also birthed a brief relationship with Newton, who had a small role as Yvette, a servant on Pitt's character Louis' plantation.

Pitt's the one who lost his head for Paltrow on the set of 1995's Se7en. They were the mid-90s couple, from the top of her slip dress to the ends of his frosted tips. Accepting the Best Supporting Actor Golden Globe for 12 Monkeys in 1996, Brad thanked Gwyneth, his "angel, the love of my life," and he proposed that December. They even had matching haircuts at one point.

"I take the institution extremely seriously. There are no divorces in my family either—and in his either, so this is not something—we've been together for quite some time, so this is not a rash decision," Gwyneth convincingly told Entertainment Tonight about their engagement. But in June 1997, they broke up.

"When two people aren't supposed to be together, they're not supposed to be together," a defiant Paltrow said in 1998. Fast-forward to 2015, when she told Howard Stern, "I was such a kid, I was 22 when we met. It's taken me until 40 to get my head out of my ass. You can't make that decision when you're 22 years old... I wasn't ready, and he was too good for me."

Moreover, her dad, Bruce Paltrow, was "devastated" when they broke up. "My father loved him like a son." Ultimately, Paltrow said, "I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt!"

The story goes that Aniston met Pitt in 1998 on a blind date set up by their agents. The world still not one for smushed-together names yet, they were simply "Hollywood's golden couple." They married in 2000, Pitt guest-starred on Friends in 2001 and in 2002 Aniston said of starting a family, "Absolutely it will happen but probably not for a while."

Alas, on Jan. 8, 2005, the actors announced they had "formally" separated. "For those who follow these sorts of things, we would like to explain that our separation is not the result of any speculation reported by the tabloid media," they said in a statement. The divorce was finalized that October amid all sorts of reports perpetuated by the people who do follow these sorts of things.

Meanwhile, Aniston's September 2005 Vanity Fair interview will go down in history as one of the rawest, most poignant breakup postmortems in celebrity history.

But years later...they're friends!

The Oscar winner eventually admitted that she and a still-married Pitt had fallen in love during the making of Mr. and Mrs. Smith in 2004.

Spurred on by their kids—Maddox, Zahara, Shiloh, Pax and twins Vivienne and Knox—Brangelina finally married at their chateau in France in 2014 after being engaged for two years.

"You get together and you're two individuals and you feel inspired by each other, you challenge each other, you complement each other, drive each other beautifully crazy," Jolie told Elle in 2014, before the surprise nuptials. "After all these years, we have history—and when you have history with somebody, you're friends in such a very real, deep way that there's such a comfort, and an ease, and a deep love that comes from having been through quite a lot together."

But Jolie filed for divorce on Sept. 19, 2016, citing irreconcilable differences and triggering an FBI investigation into Pitt's behavior on an overseas flight (he never faced charges). And though there have been periods where the dust seemed settled, the aftermath got messy and stayed messy.

They finally settled their divorce in late 2024 after an eight-year legal battle.

Ines de Ramon

After he and Jolie broke up, Pitt was rumored to be seeing a number of women, from Alia Shawkat to jewelry designer Sat Hari Khalsa to architecture professor Neri Oxman.

All filed under "just friends" in the end.

But Pitt is now in a real-deal relationship with de Ramon. He was first spotted with the jewelry company executive in November 2022—two months after de Ramon and husband Paul Wesley confirmed they had been separated since the spring. (The Vampire Diaries alum filed for divorce in February 2023.)

Meanwhile, the sightings of Pitt and de Ramon, though sporadic, simply haven't stopped.