Skip To Content

    18 Broken-Up Couples From The '90s We Never Really Talk About Anymore

    These celebs were once together?

    There are some celeb breakups that stick in our minds like glue and yet these famous couples from the '90s somehow escaped my memory.

    1. Minnie Driver and Matt Damon

    Photo of Minnie Driver and Matt Damon at a premiere
    Steve Granitz / WireImage / Getty Images

    The pair met while auditioning and filming Good Will Hunting in 1996. By 1997, they were official, attending events together and wearing tiny sunglasses. Minnie told the Telegraph in 2012, "I was blown away by his commitment to me as an actor. He was cute and intelligent, and altogether a really charming package. I was young and I fell for him. It’s an occupational hazard,” she said. Though things got complicated when Matt declared he was single on Oprah, with Minnie telling the Los Angeles Times in 1998, “It seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically inappropriate. Of course, he was busy declaring his love for me on David Letterman a month previously.”

    2. Whoopi Goldberg and Ted Danson

    Photo of Whoopi Goldberg and Ted Danson posing together
    Mitchell Gerber / Corbis/VCG via Getty Images

    This one is a wild ride. These two iconic celebs were in a secret relationship! The comedy legends met in 1988 and became friends, but things turned romantic in 1992 on the set of Made in America. Ted was married at the time to Cassandra Coates and the affair with Whoopi led to his 1993 divorce. Ted and Whoopi broke up soon after as the entire affair caused a big scandal, according to Hello! Magazine.

    3. Brooke Shields and Liam Neeson

    Photo of Brooke Shields and Liam Neeson smiling together in neutral outerwear
    Images Press / Getty Images

    They first got together in 1992 and Brooke was smitten according to her autobiography There Was a Little Girl. But the relationship only lasted a few months. Apparently, he proposed then ghosted her, Brooke revealed in an article to the Times. There's no bad blood between the two as their breakup was so long ago. Brooke even joked with Andy Cohen about Liam years later on Watch What Happens Live. 

    4. Sarah Jessica Parker and Robert Downey Jr.

    Photo of Sarah Jessica Parker and Robert Downey Jr. at a premiere
    Michael Ochs Archives / Getty Images

    These two actors first met on the set of Firstborn in 1984 and moved in with each other after a mere eight weeks of dating. The couple lived in California and would throw water balloons at their neighbors, SJP shared with People. They broke up in 1991 after seven years together and in the end, it came down to RDJ's addictions. While the two went their separate ways, they did reunite in 2015 and were able to catch up. SJP told People in 2020 that their relationship “taught me how I love."

    5. Madonna and Dennis Rodman

    Photo of Madonna in a pink dress, standing in front of Dennis Rodman

    Their courtship started in 1994 and was brief, ending after two months. Dennis wrote about their relationship in his memoir Bad as I Wanna Be, later alleging Madonna offered him money to impregnate her at the time, which she has denied. He later went on to downplay their relationship and has also alluded to the nature of their relationship in his memoir and in interviews. 

    6. Brad Pitt and Gwyneth Paltrow

    Photo of Brad Pitt and Gwyneth Paltrow smiling
    Lawrence Schwartzwald / Getty Images

    These ultra-famous celebs dated from 1994 to 1998 and were even engaged at one point. The two first met on the set of Se7en and according to E! Online, Brad called Gwyneth "the love of [his] life" in 1996 after winning a Golden Globe for his role in12 Monkeys. In 1997, they rocked matching haircuts to the premiere of The Devil's Own, with Gwyneth later telling her assistant in an Instagram Live that they went to the same stylist at the time. The couple eventually broke up that year, as they each had their own stuff to work on with Gwyneth telling Entertainment Tonight in 2015, "I was such a kid. I was 22 when we met. And it’s taken me until like 40 to get my head out of my ass. I wasn’t ready and, you know, he was too good for me."

    7. Jennifer Aniston and Tate Donovan

    Photo of Jennifer Aniston and Tate Donovan at a premiere
    Kmazur / WireImage / Getty Images

    The pair dated and broke up all before he guest-starred on Friends. Talk about awkward. They dated for three years after meeting in 1995 and were even engaged at one point before calling it off in 1998. Tate went on to guest-star as Jennifer's love interest, telling HuffPost Live in 2013 that he thought it might be a good way to "work through this breakup."

    8. Sandra Bullock and Tate Donovan

    Photo of Sandra Bullock and Tate Donovan in jackets at a movie premiere
    Ron Galella / Ron Galella Collection via Getty Images

    The former couple met on the set of Love Potion No. 9, dated for almost four years, and even got engaged before calling it quits. (Tate also dated Jennifer Aniston for a time and introduced her to Sandra, and the two have become good friends, coming together to speak with Interview in 2020. I digress...) Even after their breakup, Sandra still spoke highly of her ex, telling Vanity Fair that she still adored Tate and saying, "It’s like they say, there’s one person in your life, and Tate and I are closer than any two people I’ve ever experienced in my life. There’s nobody that means more to me, and I know for a fact that I mean the most to him, in that certain way.”

    9. Rashida Jones and Tobey Maguire

    John Shearer / Getty Images, Vittorio Zunino Celotto / Getty Images

    These celebs dated for three years, from 1997 to 2001, before their eventual breakup. While Rashida wasn't famous just yet, Tobey had already found success. There were even rumors of an engagement; though, most people never even knew they were a couple. There isn't a lot of official info out there but did find a few reports from that time.

    10. Courtney Love and Edward Norton

    Photo of Courtney Love and Edward Norton performing onstage
    Jeff Kravitz / FilmMagic / Getty Images

    The odd pairing met on the set of the 1996 film The People vs. Larry Flynt and stayed together until 1999. The couple stayed pretty low-key, keeping their relationship private, and even got engaged at one point. Courtney told Vanity Fair years later in 2003, "I love Edward so much," even though they weren't together at this point. 

    11. Courteney Cox and Michael Keaton

    Photo of Courteney Cox and Michael Keaton smiling in suits
    Jeff Kravitz / FilmMagic / Getty Images

    Courteney and Michael met before Courteney was ever famous. Introduced by mutual friends, they bonded over their dream houses, with Courtney telling People that they spent their first date talking for hours. The couple dated for five years, from 1989 to July 1995, and have remained amicable; though, they both have moved on over the years. 

    12. J.Lo and Sean Combs

    Photo of J.Lo and Sean Combs wearing all white
    Kmazur / WireImage / Getty Images

    The couple was everywhere in the '90s, oft wearing glamorous outfits. They were together from September 1999 to February 2001 with Diddy in attendance when Jennifer first wore that iconic Versace dress. Only to split on Valentine's Day that year. The couple broke it off due to cheating allegations. It seems like both stars are now in happy relationships. Jennifer told The Breakfast Club in 2019, "It was definitely a moment but I felt like it was necessary. He was meant to be in my life at that moment to teach me what I needed to know about the music business, about what kind of artist I wanted to be in the music industry."

    13. Billy Bob Thornton and Laura Dern

    Photo of Billy Bob Thornton and Laura Dern at a premiere
    Frederic J. Brown / AFP via Getty Images

    Now, this one is intense. Laura and Billy met in 1997 on Ellen and were engaged in 1999 before Laura left to film a movie. While she was gone, Billy moved out and married Angelina Jolie. Laura never heard from him again, telling Talk magazine in 2000 she didn't receive any closure or clarity regarding the situation. 

    14. Cameron Diaz and Matt Dillon

    Photo of Cameron Diaz and Matt Dillon at a premiere
    Vince Bucci / AFP via Getty Images

    They allegedly met in 1995 and broke it off in 1998 after starring in There's Something About Mary together. Cameron was truly infatuated, telling the Guardian in 1997, "I love him incredibly." The relationship eventually dwindled due to geography with Matt telling Rolling Stone in 2006, "Look, I loved her, and we were very close, but it just ran its course." 

    15. Brandy and Wanya Morris

    Getty Images, Jim Spellman / WireImage / Getty Images

    Brandy told VH1's Behind the Music that she was in love with someone, saying, "I’m just in love with somebody but can’t tell them. Too young to tell him. I can’t really tell my mom because she’ll have a heart attack as a mother and manager. What will I do?” Brandy also released a version of her song "Brokenhearted" in 1995, featuring Wanya when the two toured together as Wanya was part of Boyz II Men. The couple kept their relationship a secret, only dating for two years before ultimately breaking up in 1998 after Wanya fell in love with someone else.

    16. Kyle MacLachlan and Linda Evangelista

    Photo of Linda Evangelista and Kyle MacLachlan
    Stephane Cardinale - Corbis / Corbis Via Getty Images

    They first met on a photo shoot in 1992 when Linda was married at the time to then-president of Elite Model Management in Europe GĂ©rald Marie. They proceeded to date for six years and started seeing each other before Linda's divorce was finalized. The good-looking pair even starred in a Vogue shoot together in 1993 and were madly in love, with Kyle later telling the Evening Standard that Linda opened up the world to him. According to People, they slowly grew apart before breaking up in 1998.

    17. Jessica Simpson and Nick Lachey

    Photo of Jessica Simpson and Nick Lachey smiling on the red carpet
    Brian Zak / Gamma-Rapho via Getty Images

    They were the fairy-tale couple of the '90s, meeting in 1999 and tying the knot in 2002 before officially divorcing in 2005. The married duo also starred in a reality show called Newlyweds: Nick and Jessica from 2003 to 2005. Jessica wrote about her time with Nick in her memoir Open Book, telling People prior to its release that Nick was her first love. She said, "We worked and we were great at it. But when it came time to being alone, we weren't great at it anymore."

    18. Elizabeth Hurley and Hugh Grant

    Photo of Elizabeth Hurley and Hugh Grant at an event together
    Stephane Cardinale - Corbis / Corbis Via Getty Images

    The pair met in 1987 while filming Rowing With the Wind and stayed together for 13 years before Hugh was caught cheating. At the time, this celeb breakup rocked the gossip world. But I barely hear about this once-golden couple, aside from their still strong friendship. Elizabeth recently told People in its '90s podcast that they've been through so much together, saying, "But I've been thinking, one of the most important things to keep good relations with your exes is to have a lot of respect for their current life." Hugh told People in 2018 that the exes have remained close as their relationship has moved to become something more like "brother and sister."

    What lesser-known celeb breakup broke your heart?