Brad Pitt's greatest loves: from Jennifer Aniston, to Angelina Jolie, and Ines de Ramon
Brad Pitt has long been considered one of the most attractive men in Hollywood, so it should come as no surprise that he's dated a number of incredible women.
And there's one thing almost all of his greatest loves have in common: most of them met him while filming a movie together.
Only two of Pitt's romances break the mold, and you may be surprised to learn which two.
Keep reading to learn about each of Pitt's great loves through the years and which two women he fell for away from the studio lights.
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Jill Schoelen
Pitt's first major public romance was with fellow actor Jill Schoelen, whom he met on the set of Cutting Glass, a 1989 black comedy horror film.
They started dating after sparks flew on set and were reportedly even engaged for a few months in 1989 before Schoelen called things off.
According to The Sun, she called Pitt in tears about some "drama" while she was filming in Budapest and asked him to spend the last of his cash (remember, Pitt was still an up-and-coming actor at the time) on a plane ticket to see her.
"She called me up in Los Angeles and was crying on the phone. She was lonely and there was a huge drama.
"At this point I had $800 to my name and I spent $600 of it getting a ticket from Los Angeles to Hungary to see her," Pitt told the outlet, via CTV news.
"I got there, went straight to the set where she was filming and that night we went out to dinner. She told me that she had fallen in love with the director of the film."
According to Pitt, he told her "I'm outta here" and left.
Juliette Lewis
Pitt was connected to a string of famous ladies in the early '90s, including none other than Christina Applegate, but his next serious romance was with another co-star.
He and Juliette Lewis connected on the set of the 1990 flick Too Young to Die and started dating soon after filming wrapped, despite the fact that Pitt was 27 and Lewis was just 17.
While an age gap like that would certainly raise eyebrows now, Lewis gushed about their romance at the time.
"I already liked him as an actor, plus you gotta respect somebody who's in the same field as you," she told the Los Angeles Times in the '90s.
"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."
She added that she and Pitt wanted to work together "again and again and again", which they did... well, at least once.
The couple shared the screen again in 1993 film Kalifornia, but decided to call it quits the same year. Despite parting ways, the pair remained amicable.
"I still love the woman. 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," Pitt told Vanity Fair in 1995.
"The problem is, we grow up with this vision that love conquers all, and that's just not so, is it?"
When Lewis was asked about her ex years later, she confessed to The Guardian it felt "like a high-school relationship" in hindsight.
"I hope he finds happiness because I genuinely loved him. He's a very stand-up, good guy," she added.
Gwyneth Paltrow
Another film, another flame.
Pitt fell for Gwyneth Paltrow, who is nine years his junior, when she played his wife in the 1995 thriller Se7en and told Rolling Stone he "knew immediately" that she was the one for him.
"I got within 10 feet of her and I got goofy. I couldn't talk."
Paltrow, who was about 22, later said it was love at first sight for her too – though she was completely oblivious to the fact that her feelings were reciprocated.
"I started getting a crush on him. I'm like, 'Are you insane? You can't get a crush on Brad Pitt. Get hold of yourself,'" she told the Los Angeles Times.
They were soon an item and made their red carpet debut in 1995.
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Pitt was smitten with Paltrow and fiercely protective of the young actress, especially when now-disgraced Hollywood producer Harvey Weinstein "tried to make a pass" at the Emma actress in a hotel room in 1995.
The second she told Pitt what had happened, he confronted Weinstein.
"He said, 'If you ever make her feel uncomfortable again, I'll kill you,' " she recalled Pitt telling Weinstein during an appearance on Howard Stern's SiriusXM Radio show in 2018.
Pitt and Paltrow's romance moved quickly and they were engaged by the end of 1996.
"One night we were on the balcony of this house we were renting in this little town in Argentina," she told the Call Her Daddy podcast of the proposal in 2023.
"I wish I remembered exactly what he said, but he proposed, it was fantastic, I was thrilled. We had talked about it, but I was surprised in the moment, I remember that. I must have been 24."
Pit was 33 at the time.
Jennifer Aniston
Jennifer Aniston was one of Brad's first – and to date, only – serious romances that didn't start while filming a movie together.
The actors first met in 1994 when their managers introduced them, but Pitt was dating Paltrow and Aniston was with American actor Daniel McDonald, so it was a purely professional meeting.
But the same can't be said of the next time their managers got them in a room together, in 1998.
Both freshly single, sparks flew and in 1999 they made their relationship public when they walked the Emmy Awards red carpet together in these particularly memorable looks.
As always, Pitt fell hard and fast.
Just a few months after making their romance official, he popped the question to Aniston with a custom diamond-and-platinum engagement ring from Italian jewelry designer Silvia Damiani.
They shared the news that they were engaged in the only way a '90s power couple should: on stage at a Sting concert in New York City.
Flashing her ring for the crowd at Beacon Theatre on November 21, 1999, Aniston couldn't keep the smile off her face.
Even Sting himself looked awed by the rock.
On July 29, 2000, 36-year-old Pitt and 31-year-old Aniston tied the knot in a romantic Malibu ceremony attended by 200 guests, including plenty of famous faces.
Courteney Cox, David Schwimmer, Matthew Perry and Lisa Kudrow from Friends were all there, as were Edward Norton, Salma Hayek and Cameron Diaz, to name just a few.
As for festivities, there were 50,000 flowers strewn across the venues, four bands, and even a 13-minute fireworks display.
It was, without a doubt, the hottest celebrity wedding of the year and the newlyweds reportedly made staff working the ceremony sign a document stating that they would cop a US$100,000 (approx. $148,000 AUD) fine if they leaked any details.
... when Pitt made his now-famous cameo on Friends.
The A-lister appeared in the Thanksgiving episode of the sitcom's eighth season in November, 2001, which was titled The One with the Rumor.
In it, Pitt played Will Colbert, a former high school peer of Rachel's who launched and ran the 'I Hate Rachel Green Club' against her.
Fans were delighted to see the married couple play enemies on screen and Aniston cheekily said of her husband's short stint on the show, "Mr. Pitt was wonderful".
Though they didn't share the screen again, the couple continued working together and launched a production company, Plan B Entertainment, with producer Brad Grey in 2002.
