The 6 Most Heartbreaking '90s Celebrity Couple Breakups

No matter how much time passes after a breakup, there are just some people you never totally get over. A handful of iconic celebrity couples from the '90s give us this same feeling. Whether because of how perfect they seemed together or all the entertaining drama the created, we just can't let them go. It may have been years since these celebs broke up but we're still nostalgic for the good old days. So pass the tissues and read on for the most heartbreaking '90s celebrity couple breakups.

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Sarah Jessica Parker and Robert Downey Jr. met and started dating on the set of the thriller Firstborn in 1984 when they were both just 18 years old—and they moved in together just eight weeks later! They had a long and seemingly happy relationship, but in 1991, after nearly eight years of dating, the pair called it quits due to Downey's addiction problems.

Downey Jr. told Parade in 2008, "I liked to drink, and I had a drug problem, and that didn't jibe with Sarah Jessica, because it is the furthest thing from what she is. She provided me a home and understanding. She tried to help me. She was so miffed when I didn't get my act together. I was in love with Sarah Jessica and love clearly was not enough."

Although things didn't work out between the iconic duo, Downey Jr. has been sober since 2003. He is now married to producer Susan Downey and has two children. Parker has been married to Matthew Broderick, who she has three children with, since 1997.

Before Brad Pitt famously married Jennifer Anniston and later Angelina Jolie (which is a whole other story to tell), Pitt and Gwyneth Paltrow were Hollywood's "It" couple.

The pair met in 1994 on the set of Se7en and started dating shortly after. The glamorous duo got engaged in 2006 but never made it down the aisle, calling it quits six months later.

On The Howard Stern Show in 2015, Paltrow blamed the breakup on her young age. "I think I was a kid and I wasn't ready. He was too good for me," she said. "I honestly do think, I was too young and didn't know what I was doing."

Luckily, the duo are on good terms today. Pitt has sung Paltrow's praises and is even a fan of her lifestyle and wellness company, Goop.

"I love what Gwyneth's done [with Goop]," Pitt told British Vogue in a September 2022 interview. "She is still a really dear friend, and she has built this empire. She has always had that in her as a curator, and it's been a lovely creative outlet for her."

Actor Richard Gere and supermodel Cindy Crawford met at a backyard BBQ in 1988 when they were 39 and 22, respectively. Despite their large age gap, sparks immediately flew, but it also contributed to their demise.

In 1991, after two years of dating, the duo got married in Vegas, but things took a downwards turn and they split just four years later.

In a 2013 interview with Oprah, Crawford blamed the breakup on their big age difference. "I just think your 20s for women is such a time when you're starting to come into your own and feel your own power and connect to your inner strength and it's hard to do that—it's hard to change—in a relationship, because what one person might have signed up for, all of a sudden, you're not that anymore," she said.

Luckily things worked out for both parties in the end. Crawford has been married to Rande Gerbe since 1988, who she has two children with. Gere has been married twice since splitting with Crawford, and is now happily married to Alejandra Silva. They have been going strong since 2018 and welcomed a son together in 2019.

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Jennifer Lopez and Sean Combs aka P. Diddy (and a few other monikers) started dating in the summer of 1999 right after she released her debut album, On The 6, and were soon spotted in coordinated outfits on many a red carpet (he was her date when she wore the infamous Versace dress). But their relationship had its fair share of drama outside the style department. In the winter of 1991, they were both arrested and allegedly spent a few hours in jail after Combs got in a tousle at a club that escalated to a shootout in which three people were injured. The couple fled the scene with a gun in the trunk of their car and ended up in serious legal trouble.

The charges were eventually dropped but the whole ordeal led to many rumors about them breaking up. But according to Lopez, this was not what caused them to call it quits. In an interview with Vibe in 2003, she said it was infidelity that tore them apart.

"I was in this relationship with Puff where I was totally crying, crazy, and going nuts, it really took my whole life in a tailspin," she said. "I never caught him [cheating] but I just knew. He'd say he was going to a club for a couple of hours and then never come back that night."

Combs has said that "without a doubt" Lopez was one of his great loves, and the two have remained friendly. And now, you may have heard that Lopez reconnected with and married another former love, Ben Affleck.

Johnny Depp and Winona Ryder had a love story that captivated the public in the '90s. The pair met at the New York City film premiere of Great Balls of Fire in 1989 and according to Depp, it was love at first sight.

"I was getting a Coke," Depp said to Rolling Stone in January 1991. "It was a classic glance, like, the zoom lenses in West Side Story, and everything else gets foggy."

Within two months, the duo started dating and got engaged in July 1990. Shortly after, Depp famously got a tattoo on his right arm that read, "Winona Forever." Three years later, the pair called their engagement off and Depp later changed the tattoo, "Wino Forever."

Though the reasons for the breakup remain unclear, Depp has suggested that the media frenzy caused the split. "It's very hard to have a personal life in this town," he said in an interview with Los Angeles Times in 1993. "My relationship with Winona, it was my mistake to be as open as we were, but I thought if we were honest it would destroy that curiosity monster. Instead it fed it, gave people license to feel they were part of it."

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For almost 11 years, Nicole Kidman and Tom Cruise were one of Hollywood's hottest couples. The duo met on the set of Days of Thunder in 1990 and got married that December when Kidman was just 22 and Cruise was 28. The iconic couple adopted two children together, Isabella Jane and Connor Antony, but things ended permanently in 2001 after almost a decade together.

When speaking about the divorce, Kidman told Vanity Fair, "My life collapsed. People ran from me because suddenly it was 'Oh, my God! It's over for her now!"'

Kidman also spoke about how the marriage ultimately ended up making her feel. "I thought, I don't deserve to be here," she admitted to Glamour. "I felt it was my job to put on a beautiful dress and be seen and not heard."

Since then, Kidman met and married country singer Keith Urban and the pair have been going strong since June 2006. Cruise also remarried actress Katie Holmes, but their marriage ended in 2012.