The Gist
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Many of today’s most successful actors and actresses dated back in the ’90s and early 2000s.
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Matthew Perry and Julia Roberts briefly dated after meeting on the set of Friends, for example.
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Sandra Bullock and Matthew McConaughey were also in a relationship in the late ’90s and have been friends ever since.
In today’s nostalgia economy, the ’90s are a particularly powerful force thanks to cultural touchstones like Calvin Klein, the Spice Girls, and Carolyn Bessette Kennedy’s wedding dress. Much less attention is paid to the It couples whose love stories dominated headlines at the turn of the 20th century, however. Though not necessarily in it for the long haul, iconic pairings like Gwyneth Paltrow and Brad Pitt or Cameron Diaz and Justin Timberlake captured the attention of millions around the world—as did their breakups.
“It was the right thing at that time, but it was really hard,” Paltrow later said of that one time she broke off her engagement to one of Hollywood’s most famous actors in 1997. “There were a number of things that had happened, he was nine years older than me—he knew what he wanted, he was ready to do it and I was kind of all over the place.”
Today, many of the people who dated in the heyday of paparazzi culture are still friends despite the demise of their relationships. Ahead, here’s 10 celebrity couples you may or may not remember from the ’90s and early aughts.
01 of 10
Angelina Jolie and Billy Bob Thornton
Angelina Jolie and Billy Bob Thornton at the premiere of ‘Gone in 60 Seconds’ in June 2000.
Credit: Getty Images
Angelina Jolie and Billy Bob Thornton‘s whirlwind Y2K romance began when they met on the set of Pushing Tin in 1999. Though both actors were dating other people at the time, they soon decided to elope to Las Vegas. Laura Dern, who had been with Thornton for three years at that point, later reflected on their sudden breakup in an interview with Talk Magazine in 2000, per ABC News: “I left our home to work on a movie, and while I was away, my boyfriend got married, and I’ve never heard from him again.”
Jolie and Thorton separated in 2002; two years later, the actress coupled up with Brad Pitt, from whom she is now also divorced.
“I look at that time as a great time,” Thornton later said of his ex. “Angie is still a friend of mine and she’s a great person and she’s done so much.”
02 of 10
Kate Moss and Johnny Depp
Kate Moss and Johnny Depp at a screening of ‘Banter’ in February 1994.
Credit: Getty Images
Kate Moss and Johnny Depp met at New York City’s Café Tabac in 1994 and had a love-at-first-sight moment, according to People. “I knew from the first moment we talked that we were going to be together,” the model later recalled. They were 21 and 30 years old at the time, respectively. At the tail end of 1997, the couple broke up amid rumors of an engagement.
“There’s nobody that’s ever really been able to take care of me,” Moss lamented in 2012, per People. “Johnny did for a bit. I believed what he said. Like if I said, ‘What do I do?,’ he’d tell me. And that’s what I missed when I left. I really lost that gauge of somebody I could trust.”
03 of 10
Gwyneth Paltrow and Brad Pitt
Brad Pitt and Gwyneth Paltrow at the premiere of ‘Oblivion’ in July 2000.
Credit: Getty Images
Gwyneth Paltrow and Brad Pitt met during readings for the 1994 film Legends of the Fall and co-starred in Se7en one year later. After dating for roughly two years, Pitt proposed in December 1996. The couple broke off their engagement the following June, however.
“It was the right thing at that time, but it was really hard,” Paltrow later explained in an interview on Alex Cooper’s “Call Her Daddy” podcast. “There were a number of things that had happened, he was nine years older than me—he knew what he wanted, he was ready to do it and I was kind of all over the place.”
04 of 10
Sandra Bullock and Matthew McConaughey
Sandra Bullock and Matthew McConaughey at the premiere of ‘In Love and War’ in January 1997.
Credit: Getty Images
Sandra Bullock and Matthew McConaughey‘s chemistry in the 1996 drama A Time to Kill sparked an offscreen romance that lasted until 1998. The two actors have been friends ever since, per HuffPost, so much so that Bullock has “forged her own friendship” with McConaughey’s wife Camila Alves.
05 of 10
Julia Roberts and Matthew Perry
Julia Roberts and Matthew Perry on the set of ‘Friends’ in 1996.
Credit: Getty Images
Matthew Perry recounted his brief romance with ’90s icon Julia Roberts in his 2022 memoir Friends, Lovers, and the Big Terrible Thing. The duo had a “three-month-long courtship” that began when she appeared on an episode of Friends in 1996.
“Dating Julia Roberts had been too much for me,” he wrote, per People. “I had been constantly certain that she was going to break up with me. Why would she not? I was not enough; I could never be enough; I was broken, bent, unlovable. So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts.”
Perry passed away nearly 30 years later in October 2023. In an interview with Entertainment Tonight, Roberts called his death “heartbreaking.”
“I think that, you know, it just helps all of us just appreciate what we have and to keep going in a positive way as best we can,” she added.
06 of 10
Nicolas Cage and Lisa Marie Presley
Nicolas Cage and Lisa Marie Presley at the premiere of ‘Windtalkers’ in June 2002.
Credit: Getty Images
Nicolas Cage and Lisa Marie Presley‘s high-profile relationship dominated headlines when the duo got together in the early 2000s. According to People, the actor was still legally married to Patricia Arquette at the time; Presley, meanwhile, was engaged to singer-songwriter John Oszajca. Following a meet-cute at a Halloween party in 2000, the duo got married on August 10, 2002, which just so happened to be the 25th anniversary of Elvis Presley‘s death. The newlyweds filed for divorce less than four months later.
“I’m sad about this, but we shouldn’t have been married in the first place,” Presley said in a statement issued by her publicist Paul Bloch, per CNN. “It was a big mistake.”
The late singer, who passed away in 2023, also opened up about their short-lived marriage in an interview with Rolling Stone in 2003. “We’re both so dramatic and dynamic that when it was good, it was unbelievably good, and when it was bad, it was just a fucking bloody nightmare for everybody,” she said. “It was just Mr. Toad’s Wild Ride.”
07 of 10
Tom Cruise and Cher
Tom Cruise and Cher backstage at the Love Rocks concert in February 2002.
Credit: Getty Images
Tom Cruise and Cher were “linked” in the mid ’80s, per The Cut, when the actor was 23 years old and the Goddess of Pop was 38. Though their romance was brief, Cher later gave credit where credit was due during an appearance on Watch What Happens Live With Andy Cohen.
“I’ve had just the greatest lovers,” she said in December 2013. When asked where Cruise ranked on her list, she revealed, “He was in the top five.”
08 of 10
Cameron Diaz and Justin Timberlake
Cameron Diaz and Justin Timberlake at a Los Angeles Lakers game in April 2006.
Credit: Getty Images
Cameron Diaz and Justin Timberlake met at the 2003 Kids Choice Awards and went on to date for about four years before calling it quits in 2007. Despite a highly publicized split, they remain good friends and even co-starred in the 2011 comedy Bad Teacher.
“Justin and I have always had a good laugh together, and to make a movie where we get to have a laugh together, and there really was no one else who was more perfect for this part,” Diaz told US Weekly in March 2011 of her ex’s role in the film. “He’s frickin’ weird in movies. He’s so bizarre and hilarious. I say that with great respect to his character and what he’s done!”
09 of 10
Ryan Reynolds and Alanis Morissette
Ryan Reynolds and Alanis Morissette at the 2003 MTV Movie Awards.
Credit: Getty Images
Ryan Reynolds and Alanis Morissette were brought together by Drew Barrymore back in 2002 when the duo met at the talk show host’s birthday party. They began making joint red carpet appearances in 2003 and got engaged in 2004. By 2007, however, they had called it quits.
“They remain close friends and continue to have the utmost love and admiration for each other,” their reps said at the time in a statement shared with People. “They ask that their privacy be respected surrounding this personal matter.”
Morissette addressed the breakup the very next year with the release of her album Flavors of Entanglement. “I’ve been on a constant journey toward finally surrendering and hitting the rock bottom that I’ve been avoiding my whole life…So this was a huge, critical juncture for me,” she explained at the time. “Everything broke, and it was an amazing and horrifying time.”
10 of 10
Madonna and Tupac Shakur
Madonna and Tupac Shakur at a party hosted by Interview Magazine in March 1994.
Credit: Getty Images
Madonna‘s brief ’90s romance with Tupac Shakur was kept entirely under wraps until the “Like a Virgin” singer confirmed it during a March 2015 appearance on The Howard Stern Show. In reference to a tense 1994 interview on The Late Show with David Letterman, Madonna attributed her mood to the late rapper: “I was dating Tupac Shakur at the time, and the thing is…he got me all riled up on life in general.” Though we now know that the couple met in 1993 and broke up in 1995, little else has been shared about their secret relationship.
Read the original article on InStyle
