Unexpected Celebrity Couples From The '90s You May Have Forgotten About

This article references racism and substance misuse.

Before the internet era, keeping up with your favorite celebrity couples was hard! There wasn't the instant gratification of every red carpet appearance inspiring endless tweets, and there were no snuggled-up selfies on Instagram. Instead, the celeb-obsessed of the '90s had to settle for scraps, gleaning snippets of info from tabloids in the supermarket checkout line or watching "Entertainment Tonight" religiously.

But nowadays, the world wide web makes keeping up with our favorite '90s couples hella easy. Some stars whose love stories fascinated us back in the day survived Y2K and are still going strong, such as Sarah Jessica Parker and Matthew Broderick, Will Smith and Jada Pinkett Smith, Victoria Beckham and David Beckham, and Kelly Ripa and Mark Consuelos. Then there are the rare stories about two '90s stars finding each other long after the era of No Fear tees and those wicked cool windsuits that were a dozen different unnatural colors. "Boy Meets World" actor Matthew Lawrence told ET that he had his own '90s rom-com meet-cute with TLC member Chilli on a flight, and they confirmed that they were a couple in 2023. "She's a really, really special human being," Lawrence said of his talented boo. "I wish more people on the planet were like her. We'd be much better off." It's good to know that Chilli's no-scrub game is still going strong.

But for every totally dope '90s match that go together like Cher and Josh in "Clueless," there's an unlikely pair that eventually peaced out.

After taking a break from Hollywood to attend Princeton University, '80s It girl Brooke Shields staged a career comeback on television, starring in the popular sitcom "Suddenly Susan" in the '90s. Four years before the show's 1996 premiere, "The Blue Lagoon" star dated "Schindler's List" actor Liam Neeson.

In her memoir, "There Was a Little Girl: The Real Story of My Mother and Me," Shields confessed to hoping that her relationship with an in-demand leading man would inspire better job offers her way. However, this wasn't the only reason she was "Taken" with Neeson. "He was a tall Irish actor and a drunk who was thirteen years my senior. He wooed me with his brogue, his poetry, and his s***ty choice of cheap pinot grigio wine," she wrote. Their relationship became serious enough that Neeson popped the question. But before ghosting was a thing, Shields says that Neeson did it to her three months into their relationship, flying home one day and ignoring her request to call her when he got there.

Shields told People that Neeson later tried to pick up where they left off and even proposed again, explaining, "I said, 'No, no, no, because knowing you, you'll probably fall in love with your next leading lady and marry her.'" And she was right: In 1994, Neeson went on to marry Natasha Richardson, his co-star in the play "Anna Christie."

In the '90s, "Cheers" actor Ted Danson and "Sister Act" star Whoopi Goldberg were a match made in comedy heaven — until a comedy act threatened to turn Danson into a persona non grata. When he made headlines for wearing blackface, it would still be over two decades before cancel culture discourse would become a major part of social media's DNA.

Danson had already courted controversy by beginning his relationship with Goldberg when he was still married to Cassandra Coates. But he really got burned by the media after participating in a Friars Club roast of Goldberg in 1993. In addition to making himself look like a racist caricature, he used a racial slur multiple times and made offensive jokes about mixed-race children. When it was her turn to speak, Goldberg said to the audience, "It takes a whole lot of [courage] to come out in blackface ... I don't care if you don't like it. I do,″ according to AP. During a press conference, she reiterated that she wasn't offended by Danson's material and even revealed that she'd helped him plan his routine, per People.

A month later, the couple ended their relationship after 18 months of dating. Goldberg took the breakup hard. "The loss of his friendship hurts a great deal," she told Closer Weekly. "We can never go and have a soda anywhere. I'm friends with almost every man I've gone out with, except this man."

Sarah Jessica Parker and Robert Downey Jr.'s Hollywood love story ended before she got cast in "Sex and the City" — and long before he assumed the role of the Marvel mogul who collects suits of powered armor like Carrie Bradshaw accumulates designer shoes. The actors were filming the 1984 thriller "Firstborn" when they fell in love. "I guess Sarah thought I looked scary enough to be interesting," Downey joked to People in 1985. He credited Parker for helping him become more financially responsible and mature and even said that their relationship had given his career a boost. "I thank God for Sarah Jessica Parker," Downey's father said. "Without her, Robert would go at 100 miles an hour into a brick wall."

At age 20, SJP and RDJ were already thinking about getting married. But by the early '90s, Downey's substance use issues had taken a serious toll on their relationship. "There was a huge amount of time spent making sure he was okay," Parker told People in 2018. "At a certain point, I had the courage to say, 'I'm going to walk away and I'm just going to pray that you don't die.'" 

Thankfully, Downey eventually got sober. In a 2015 appearance on "The Howard Stern Show," he revealed that he'd recently caught up with Parker over dinner. "I said everything I wanted to say," he recalled. "... It's a little bit stilted but then there's this familiarity that overtakes it."

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

They both made names for themselves on television series set in past decades, with Ashton Kutcher rocking bell bottoms on "That '70s Show" and January Jones portraying a bored '60s housewife on "Mad Men." But when the actors started hangin' out, it was the late '90s. A few months into the new millennium, they were cohabitating, per People. 

In a 2009 GQ interview, Jones mentioned a certain ex-boyfriend who predicted that she wouldn't succeed as an actor. "He only has nice things to say now — if anything, I should thank him," she added. "Because the minute you tell me I can't do something, that's when I'm most motivated." Her interviewer assumed that the ex was Kutcher, but Jones wouldn't confirm this when asked about it on "Watch What Happens Live."

According to that same GQ profile, Bruce Willis once predicted that Jones would be a star based on her name alone. The two appeared together in the 2001 movie "Bandits," and if Demi Moore is to be believed, this caused some friction between Jones and Kutcher. In her memoir "Inside Out" (via Radar), Moore detailed her past marriages to Willis and Kutcher. Apparently, Kutcher told her that he believed Jones had cheated on him with Willis. She even recalled a conversation she and the "Mad Men" star had about his suspicions and wrote that Jones said to her, "I told him a hundred times, I didn't want to f*** that old man!"

When Liv Tyler and Joaquin Phoenix were cast as love interests in the 1997 coming-of-age film "Inventing the Abbotts," Liv had already stepped out of the shadow of her famous father, Aerosmith frontman Steven Tyler, and established herself as a '90s style icon in one of the era's quintessential films, "Empire Records." Meanwhile, Joaquin was busy proving that he deserved recognition beyond being the brother of late star River Phoenix, earning critical acclaim for his performance in the 1995 dark comedy "To Die For."

In a 1997 interview with The Morning Call, Liv gushed, "I fell in love with Joaquin the second I saw him," while Joaquin said that he initially viewed Liv as a dear friend. He also confessed that he had no clue who she was when they first met, although he did remember seeing her in a shampoo ad. The romance between the future stars of "Gladiator" and "The Lord of the Rings" trilogy didn't survive past the '90s, with Joaquin revealing that their relationship had become a bit too uneventful for his liking. "When you become satisfied, you stop fighting, and I like fighting," the "Joker" star explained to Cosmopolitan in 1999.

But maybe that absence of arguments helped them remain friends. "I consider Joaquin and all of his sisters to be like family," Liv told Elle in 2015. "He was my first love. So he's a huge part of even my sense of humor."

When "The Mighty Ducks" star Emilio Estevez first reached out to MC Skat Kat's dance partner in 1990, Paula Abdul was dating one of the decade's other biggest heartthrobs, "Full House" actor John Stamos. There was no sliding into DMs back then, so Estevez had to phone Abdul to let her know that he was an admirer. They became coil-cord confidants, and after Abdul's romance with Stamos ended, fate intervened. Upon learning that they were both Plaza Hotel guests, Estevez asked Abdul out on a date. "After that, he would send flowers or letters to every city I was in," Abdul recalled to People. "We would have phone conversations and visit every few weekends. We thought everything was perfect."

After Abdul and Estevez tied the knot in 1992, their relationship remained blissful until it came time to discuss one very important topic: starting a family together. The "Repo Man" star decided that he was content with the two children he shared with his ex Carey Salley, while Abdul wanted to experience motherhood herself. "It was heartbreaking for us both," she said of the realization that their relationship just wasn't going to work.

Abdul never did have children, but she did become a proud dog mom. "Playing with my dogs and taking them for long walks is huge for my self-care," she told SheKnows in 2019. "They're my four-legged family members and they bring so much happiness to my life!"

While reigning supreme as a '90s pop-rock queen, "All I Wanna Do" hitmaker Sheryl Crow preached about the importance of having a little fun before we die and chronicled a dying relationship in the earworm "My Favorite Mistake." She also played a woman with a drug addiction who died at the hands of a serial killer in the 1999 movie "The Minus Man" — and fell for the actor who pretended to kill her.

Per E! News, Crow used the liner notes of her album "C'mon, C'mon" to reveal that her song "Safe and Sound" was about her relationship with her co-star, Owen Wilson. "I don't blame you for quitting, I know you really try," she sings. She also repeats the words, "Feel like I could've saved you" at the end of the song, which was released five years before Wilson's 2007 suicide attempt.

Wilson accepts the bulk of the responsibility for his failed relationship with Crow. "I was lucky enough to find a great girl and, because of my lack of focus, the relationship went south," he told the Irish Examiner in 2011, admitting that this was once his modus operandi when it came to relationships. He also insisted that fame had nothing to do with their split, although Crow told Good Housekeeping that dating fellow celebrities usually proved disastrous for her back then. "What ends up happening is that one of you becomes smaller," she reasoned. "And it was always me."

Sam Neill played Laura Dern's love interest in the 1993 blockbuster "Jurassic Park," but behind the scenes, Jeff Goldblum was so preoccupied with falling for her that he didn't stop to think if he should. "I'd been a big fan of hers," he told the Chicago Tribune. "I think she's an amazing actress and a spectacular person. I was struck from the beginning." However, the co-stars waited until they were done getting elbow-deep in dino-doo before they started dating. Their relationship lasted four years, but their two-year engagement did not result in a wedding with dilophosaurus flower girls. "We're not traditionally together right now. I respect her, adore her acting, adore her as a person," Goldblum told The New York Times in 1997. "Relationships are challenging, aren't they?"

After she and Goldblum called it quits, Dern had another very '90s relationship with "Sling Blade" star Billy Bob Thornton. Dern and Thornton were engaged when the '90s ended, but in May 2000, Thornton married Angelina Jolie — without dumping Dern first. "I've never heard from him again," Dern told Talk magazine (via ABC News) a few months later. "... It's like a sudden death."

Thankfully, her split with Goldblum wasn't so messy. While speaking about reuniting with her former castmates to film the 2022 sequel "Jurassic World: Dominion," Dern told The Guardian, "Steven [Spielberg] and Jeff and Sam became my family. And remained my family all these years."

Isn't it ironic that Dave Coulier had no idea how badly he'd hurt Alanis Morissette until he heard "You Oughta Know" on the radio? By definition, no. But in Morissette's mind, maybe? The singer who made high school English teachers groan by complaining about the non-irony of rain ruining wedding days and flies bathing in Chardonnay also gave us one of the '90s most scathing takedowns of an ex. And according to music lore, the man who needed reminding of the mess he made was none other than the goofy comedian who was pals with a woodchuck puppet on "Full House."

Morissette addressed the speculation about who "You Oughta Know" might be about on "Watch What Happens Live" in 2019, where she said that half a dozen people had come forward to claim they inspired the song. "If you're going to take credit for a song where I'm singing about someone being a douche or an a***ole, you might not want to say, 'Hey! That's me!'" she pointed out. But in a 2022 appearance on "Jim Norton & Sam Roberts," Coulier recalled listening to the lyrics for the first time and thinking, "Oh no! Oh, I can't be this guy!" He then purchased Morissette's "Jagged Little Pill" album. "There was a lot of familiar stuff in there," he said. "I thought, 'Ooh, I think I may have really hurt this woman."

Counting Crows got plenty of radio airplay in the '90s, thanks to the enigmatic hit "Mr. Jones." In the song, frontman Adam Duritz dreams of being a big star, but he got a little more fame than he bargained for when he dated two stars of the sitcom "Friends." First, there was Jennifer Aniston, who would later bring us one of the most memorable couples of the '90s by dating Brad Pitt. 

On Vice TV's docuseries "Dark Side of the '90s," Duritz revealed that he didn't know who Aniston was when they were tricked into talking to each other while hanging out at The Viper Room. "A bunch of my friends lied to me and told me she had a crush on me," Duritz recalled, per ET. "Those same friends lied to her and told her I had a crush on her." He revealed that his romance with Aniston was brief, but he remembered her fondly. "She's a nice girl," he said. Duritz later also dated Aniston's "Friends" castmate Courteney Cox, who appeared in the music video for "A Long December." Cox sandwiched their romance between long-term relationships with "Batman" actor Michael Keaton and her "Scream" co-star David Arquette.

Apparently, Duritz doesn't like to talk about his relationships with Cox and Aniston too much — the tabloid attention they attracted was a distraction from his music. "It wasn't great for me, it wasn't great for my band," he told Men's Health in 2014.

If you don't remember who Madonna dated in the '90s, it might be because she spent the decade collecting famous beaus like Pokémon while also finding time to slay onstage and churn out bangers. The Material Girl caught the eye of Warren Beatty when he played the titular private eye in the 1990 comic book movie "Dick Tracy." Madonna also seduced him on-screen as nightclub performer Breathless Mahoney. "She's a huge personality, diligent and disciplined, and a spectacular dancer and performer," Beatty said of his ex in a 2016 interview with People. "She's a phenomenon."

Vanilla Ice wasn't as nice when discussing his eight-month romance with Madonna. He told News of the World (via Digital Spy) that he dumped her after she posed for suggestive photos with different men and had them published in her book "Sex." He complained, "I was hurt to be an unwitting part of this slutty package. It was disgusting and cheap." The "Ice Ice Baby" hitmaker wasn't the only rapper Madonna got dumped by in the '90s. In 2017, TMZ published a prison letter from Tupac to the "Like a Prayer" singer in which he explained that their relationship was bad for his image.

Then there was NBA star Dennis Rodman. On "The Breakfast Club," he claimed that Madonna once offered him $20 million to get her pregnant. She even sent a private jet to pick him up when she was ovulating. But alas, the flight was not fruitful.

"Never Been Kissed" star Drew Barrymore ended the '90s on an unexpected note by dating the titular host of the zany MTV series "The Tom Green Show." In a 2020 interview with ET, the actor-turned-talk-show-host described Tom Green as a trailblazer while discussing their relationship. "He was doing reality television before there was reality television, so as his girlfriend and supporter of that, I was on a ride I did not totally understand," she said.

The couple met when Barrymore reached out to the Canadian comedian to see if he was interested in appearing in the 2000 movie "Charlie's Angels." They tied the knot in 2001, but before you could say, "My bum is on the phone," they found themselves all alone.

The exes reminisced about their short-lived relationship when Green appeared on "The Drew Barrymore Show" in 2020. Barrymore got emotional after her ex-husband praised her for bringing so much joy to her viewers, and he regaled the audience with his recollection of one of their first dates. According to Green, he and the actor bonded over their appreciation of animals by purchasing some lucky lobsters and returning them to the sea. Green also surprised Barrymore by drinking out of a mug that featured a photo of his ex wearing a neck brace, a memento he kept from their time together. "We had a lot of amazing, amazing experiences, and I'm grateful for that, and I cherish them," he said.

"Dumb and Dumber" goofball Jim Carrey and "Jerry Maguire" star Renée Zellweger learned that their love story was being written for them before it actually began. They became friends while filming "Me, Myself & Irene" at the end of the '90s, but it angered Zellweger when the tabloids suggested that there might be something more going on. "I said, 'No, it's not true,'" she recalled to CNN. "And then I went home ... and I went, 'God, I do miss him.'"

As for Carrey, the "Man on the Moon" star seemed over the moon that Zellweger started viewing him as more than a co-star and close pal after they wrapped filming. "I will say that we had the most wonderful, old-fashioned, tremendously something-you-dream-about-happening-and-never-happens-anymore type of courtship," he said. He also told Entertainment Weekly that Zellweger helped him find a renewed sense of normalcy in his life. "She thinks having a good time is renting a U-Haul and taking furniture to Texas," he revealed. "She's real in that way and I absolutely love it." But he denied reports that Zellweger had hired clowns to perform stripteases for him because his performance in "Man on the Moon" didn't earn him an Academy Award nomination.

Although the couple's relationship only lasted a year, Zellweger left a lasting impression on Carrey. "She definitely was special to me, very special. I think she's lovely," he said in a 2020 appearance on "The Howard Stern Show."

Courtney Love's most unforgettable '90s relationship was unquestionably her marriage to the late Nirvana frontman, Kurt Cobain. However, the Hole frontwoman told The Times that she had another famous beau who she missed an opportunity to settle down with — her "The People vs. Larry Flynt" co-star Edward Norton. He was so near and dear to her that she asked him to be the godfather to her and Kurt's daughter, Frances Bean Cobain.

"I left him for a bad man who stole all my money," Love admitted. "I left Ed Norton, who was good and wonderful, for an average bad man who was in A&R. It's upsetting." She'd previously told Vanity Fair (via the Irish Examiner) that the reason she left Norton was work-related. "I dumped him for a movie role. If that isn't shallow, I don't know what is," the "Celebrity Skin" singer said.

According to Love, she also missed out on a chance to reunite with Norton on-screen when they were still dating. On the "WTF" podcast, she told host Marc Maron that she was supposed to appear alongside him in the 1999 cult classic "Fight Club," as Marla Singer. However, she claimed that another star of the film, Brad Pitt, got her fired after she lashed out at him for pitching her a movie in which he would have played her late husband. "I went nuclear," she said. According to Love, Norton was crying when he told her that she'd gotten the axe. 

While a popular '90s boy band star seemed like the perfect match for "Boy Meets World" actor Danielle Fishel, she eventually learned that *NSYNC singer Lance Bass wasn't interested in being the other player in her game for two. But the night of her senior prom, Fishel was just a girl who was convinced that her date was the one. Bass was that date, telling Rolling Stone that his relationship with Fishel began when he got bandmate Justin Timberlake to ask her for her digits during the filming of a "TGIF" special.

The relationship lasted almost a year, but another *NSYNC member tried to warn Fishel that she was headed for heartbreak. "Chris Kirkpatrick would say, 'You know your boyfriend's gay, right?' At the time, I thought of it as making a joke,'" Fishel recalled. She was distraught when Bass dumped her in 1999 and didn't believe his explanation that distance was the issue. "I held onto hope for way too long that Lance and I were gonna get back together and get married and have a family," Fishel confessed on "Pod Meets World."

The exes remained friends, with the actor telling Rolling Stone that Bass came out as gay to her before he made his public announcement in 2006. They also came to love their non-romantic love story so much that they decided to turn it into a movie in 2022. "The writers have so aptly titled it an un-romcom," Fishel told Rolling Stone.