15 celebrity couples who ruled the 1990s

Bruce Willis and Demi Moore were married throughout the ’90s, and they remained on good terms after their split.

Bruce Willis and Demi Moore were married from 1987 until 2000. They met at a movie screening and were married just a few months later in Las Vegas.

“We were moving to the gambling tables when Bruce said, ‘I think we should get married.’ We’d been joking about it on the flight there, but suddenly it didn’t seem like he was kidding,” Moore wrote in her memoir, according to The Sun.

Willis and Moore called it quits in 1998 but are still friends. They share three daughters: Rumer, 33; Scout, 30; and Tallulah, 28.

Gwyneth Paltrow and Brad Pitt looked and dressed eerily similar while they were dating.

Gwyneth Paltrow and Brad Pitt dated from around 1994 to 1997 after meeting on the set of “Se7en.” They were a red-carpet power couple, and they even sported matching haircuts and outfits.

However, despite Pitt proposing, the two ended things in 1997.

“I was such a kid,” Paltrow told Howard Stern in 2015, adding: “You can’t make that decision when you’re 22 years old … I wasn’t ready, and he was too good for me … I didn’t know what I was doing.”

Ben Affleck and Gwyneth Paltrow were also a power couple in the late ’90s.

The pair had previously met at a dinner party hosted by now-disgraced producer Harvey Weinstein and went on to be costars on the set of “Shakespeare in Love” and “Bounce.”

They called things off in 2000.

“I just think we have a very different sort of value system,” Gwyneth told Entertainment Weekly in 2003, adding that he was “a great guy.”

Paltrow recently gave her blessing to her ex and Jennifer Lopez, who reunited in 2021 after their split in 2004.

“Okay, this is cute,” Paltrow commented on a pic of Affleck and Lopez kissing in September, according to Page Six.

Winona Ryder and Matt Damon were introduced by Gwyneth Paltrow while she was dating Affleck.

Winona Ryder and Matt Damon had a brief but public romance, and they even attended the Golden Globes together in 2000. However, not long after that, they split up amicably.

“Matt couldn’t be a greater, nicer guy. I’m really lucky that I’m on good terms with him,” Ryder told Black Book in 2009.

Johnny Depp and Winona Ryder got engaged in 1990 but split three years later.

Johnny Depp and Winona Ryder’s whirlwind romance became one of the most iconic relationships of the 1990s.

The pair met in 1989 when Ryder was just 18 and Depp was 27, while Ryder was buying a Coke at the premiere of “Great Balls of Fire!” in the lobby of New York’s Ziegfeld Theater.

“It was a classic glance,” Depp said, according to Rolling Stone, “like the zoom lenses in ‘West Side Story,’ and everything else gets foggy.”

Ryder recalled that when she met Depp, she was a “pure virgin” and had never been in a relationship before.

“There’s been nothing in my 27 years that’s comparable to the feeling I have with Winona,” Depp told People after meeting Ryder.

Five months after meeting, the pair were engaged. Depp also famously got “Winona Forever” tattooed on his right arm, which he altered to “Wino Forever” after the pair split in 1993.

Kate Moss and Johnny Depp’s passionate romance was the talk of the town in the late ’90s.

Kate Moss and Johnny Depp dated from 1994 to 1998. However, despite only dating a few years, they certainly made an impact as one of the chicest couples of the ’90s.

During that time, they had a few famous bust-ups, including the time Depp destroyed his room at the Mark Hotel in New York City in 1994 — felony mischief charges were dropped after he paid more than $9,000 in fines. Depp also reportedly filled a bathtub with bottles of champagne worth $1,000.

“There’s nobody that’s ever really been able to take care of me. 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,” she told Vanity Fair in 2012. “I really lost that gauge of somebody I could trust. Nightmare. Years and years of crying. Oh, the tears!”

Richard Gere and Cindy Crawford married in 1991. At the time, she was just 25 years old and Gere was 42.

The “Pretty Woman” heartthrob and supermodel met at a barbecue hosted by photographer Herb Ritts in the late 1980s. A few years later, the pair spontaneously wed in a Las Vegas ceremony complete with aluminum foil wedding rings.

However, Gere and Crawford split in 1995 after four years of marriage.

“I think part of the problem in our relationship was that we were a lot of other things but I don’t know if we were ever friends — like peers, because I was young, and he was Richard Gere,” she explained in an interview with Marc Maron on his podcast in 2016. “And then, as I started kind of growing up and growing into myself — it’s hard to change the nature of a relationship once you’re already in it.”

Crawford also said she and Gere haven’t really kept in touch after they went on to marry other people.

Pamela Anderson and Tommy Lee had a public romance in the 1990s and reconnected time and time again over the years.

Pamela Anderson and Tommy Lee got married in 1995, just days after meeting. Throughout their four-year-long marriage, the pair were consistently involved in one scandal or another, from over-the-top public displays of affection to a leaked sex tape that was recently documented in the 2022 Hulu series “Pam & Tommy.”

Anderson and Lee finally called it quits in 1998, but they went on to have an off-and-on relationship over the following decade. They share two children: Brandon Thomas Lee, 25, and Dylan Jagger Lee, 24.

Whitney Houston and Bobby Brown had a volatile relationship after meeting in 1989.

Whitney Houston and Bobby Brown met at the Soul Train Music Awards in 1989, when both were at the top of the music charts. However, it wasn’t exactly love at first sight.

“I and some friends of mine were sitting behind him,” Houston told Rolling Stone of their first encounter.”I was hugging them, we were laughing, and I kept hitting Bobby in the back of the head … I leaned over and said, ‘Bobby, I’m so sorry.’ And he turned around and looked at me like, ‘Yeah, well just don’t let it happen again.’ And I was like, ‘Oooooh, this guy doesn’t like me.’ Well, I always get curious when somebody doesn’t like me.”

Their relationship weathered many ups and downs. According to Biography, Houston turned down Brown’s first marriage proposal, but they were eventually married on July 18, 1992. In March 1993, Bobbi Kristina Brown, their only child, was born.

However, in the mid-2000s, news broke of problems in their marriage, including drug use and rumors of infidelity. During the marriage, Brown had multiple run-ins with the law. In 2003, he was accused of striking Houston across the face, however, he was not convicted and denied ever hitting her. Houston also entered rehab on two occasions for her drug abuse.

“I never cheated, I never did none of that stuff,” she told Oprah Winfrey in 2009, two years after the pair divorced. “I just did the drugs.”

Whitney Houston passed away on February 11, 2012, after accidentally drowning in her bathtub. Their daughter, Bobbi Kristina, passed away in 2015.

Hugh Grant and Elizabeth Hurley were together for 13 years before splitting in 2000.

According to InStyle, Hugh Grant and Liz Hurley met on the set of Spanish film “Remando al viento,” or “Rowing with the Wind,” in 1987. The pair quickly became one of the most photographed couples in the world.

However, their relationship hit a snag when Grant was famously arrested in 1995 for soliciting lewd conduct with sex worker named Divine Brown. He was later sentenced to pay a $1,000 fine and attend an AIDS training program, according to The Guardian.

“I felt like I’d been shot,” Hurley told Barbara Walters in 1995 of her initial reaction to Grant’s indiscretion.

The pair managed to work through the scandal and stayed together for another five years before breaking up. They’ve remained friends over the years.

Nicole Kidman and Tom Cruise were together throughout the decade.

Nicole Kidman and Tom Cruise met while working on “Days of Thunder” and were married from 1990 to 2001.

“He basically swept me off my feet,” Kidman told Vanity Fair in 2002. “I fell madly, passionately in love. And as happens when you fall in love, my whole plan in terms of what I wanted for my life—I was like, ‘Forget it. This is it.’ I was consumed by it, willingly.”

Despite appearing to be one of the most steadfast couples in Hollywood, Kidman and Cruise later divorced.

Cruise went on to marry actress Katie Holmes in 2006, but they divorced in 2012. Also in 2006, Kidman wed country singer Keith Urban, with whom she has two children.

Kurt Cobain and Courtney Love defined the grunge scene of the ’90s.

Kurt Cobain and Courtney Love met in a nightclub in 1990 and got married just a few months after meeting – a running trend for many ’90s couples, it appears.

At the time, Nirvana was at the height of its popularity. The couple became pregnant with daughter Frances Bean a few months into their marriage, during which time they tried to get clean from drugs.

Their relationship ended in tragedy when Cobain died in 1994 at 27 years old.

“He is considered to be the rock star who didn’t want fame, the weak pathetic guy who was taken over by this controlling female, and yadda yadda,” Love told Loudwire in 2015. “He’s a hard act to follow. I love him and I always will.”

David Bowie and supermodel Iman met in 1990.

David Bowie and Iman met in 1990 at a dinner party, where it was apparently love at first sight for the “Rebel Rebel” singer.

“My attraction to her was immediate and all-encompassing,” he told Hello! magazine in 2000. “I couldn’t sleep for the excitement of our first date. That she would be my wife, in my head, was a done deal. I’d never gone after anything…with such passion in all my life.”

The pair married two years after meeting. Iman later said that they fell in love with who they were to each other behind the scenes.

“I didn’t want to get into a relationship with somebody like him,” she told The Guardian in 2004, according to Biography. “But as I always said: I fell in love with David Jones. I did not fall in love with David Bowie. Bowie is just a persona. He’s a singer, an entertainer. David Jones is a man I met.”

The pair kept their marriage and relationship relatively out of the spotlight after Bowie gave up touring in 2004. On January 10, 2016, the iconic artist passed away at the age of 69 from liver cancer.

“I will never remarry,” she told Porter magazine afterward. “I mentioned my husband the other day with someone, and they said to me, ‘You mean your late husband?’ I said, no, he is always going to be my husband. … I do feel very lonely. But do I want a relationship? I can’t say never, but no, not now.”

David and Victoria Beckham tied the knot in 1999 and are still going strong.

David and Victoria Beckham met in 1997 when she was well known as “Posh Spice” and Beckham was reaching international fame for Manchester United. In fact, it was the team that brought them together.

“Yes, love-at-first-sight does exist,” Victoria told British Vogue in 2016. “It will happen to you in the Manchester United players’ lounge — although you will get a little drunk, so exact details are hazy.”

The pair got engaged in 1998 and wed a year later in a lavish ceremony in Ireland. Over their decades of marriage, David has reportedly gifted Victoria 14 different engagement rings, according to W Magazine.

They have now been married for 22 years and share four children: Brooklyn Beckham, 22; Romeo James Beckham, 19; Cruz Beckham, 16; and Harper Seven Beckham, 10.

Justin Timberlake and Britney Spears became the ultimate pop power couple when they began dating in 1998.

While Justin Timberlake and Britney Spears’ relationship didn’t reach superstar status until the early 2000s, they began dating in the late ’90s, years after meeting on the set of “The Mickey Mouse Club.”

“When people [in the public] get too personal, it bothers me. But I’m not ashamed at all to say that I love him from the bottom of my heart. As far as love is concerned, with him, too much is not enough. He’s everything,” she told The Guardian in 2001. “It is a deeper love now than when I was younger. Like, we’ve gone through so much together and we’ve known each other since we were 12 years old. We know each other inside and out.”

Britney and Justin broke up in 2002, not long after cementing themselves as an iconic power couple.