#30. Matthew McConaughey and Sandra Bullock
Yup, these two were a thing. Matthew McConaughey and Sandra Bullock met on the set of 1996’s A Time to Kill, and fell madly in love. Bullock has always been very private when it comes to her love life, and this relationship was no exception. She repeatedly denied being in a relationship with McConaughey and said they were just friends, but the paparazzi proved the opposite. They were often seen in public, especially doing enough PDA to consider them an item.
The relationship between the two Oscar winners lasted for two years before it ended abruptly. However, this wasn’t the end of their friendship, as they’re still very good friends even after all these years —20, to be exact. McConaughey and his wife Camila Alvez are both close with Bullock and their kids have regular playdates together. The chemistry is obviously still there, but their palpable connection evolved into a beautiful friendship that has stood the test of time.
#29. Seal and Tyra Banks
We all remember singer Seal‘s long relationship with German supermodel Heidi Klum, but the public seemed to forget he also dated another famous supermodel: Tyra Banks. The two were spotted together back in 1996 and later made only one public appearance together. Although they were clearly seen in public, their relationship was always kept under the radar, and sadly only lasted for a few months. It ended just as quickly as it started, and they didn’t get to Seal the deal.
Although the two never spoke about what led them to break up, it is believed that it was the age gap between them that made things difficult. Seal was 34 at the time, while Banks was only 23. 11 years can really make a difference when it comes to a relationship, especially when you’re very young. Seal recovered from the breakup very quickly though and settled down with model Tatiana Patitz for six years until he started dating Heidi Klum. Someone has a taste for supermodels, doesn’t he?
#28. Neil Patrick Harris and Christine Taylor
At this point, we all know who Neil Patrick Harris is: a wonderful actor, and incredible dancer and performer, and an openly gay man. So hearing that he went out with Christine Taylor in the ’90s sounds completely bizarre right now. But, going back 20 years ago, the world wasn’t as accepting as it is today, and therefore, Harris was still in the closet. In fact, he wasn’t even sure about his sexuality at that time, as he told Howard Stern in an interview.
“She’s the coolest, nicest chick ever. She’s an absolute catch. And I thought, ‘If I’m not going to feel the super sparks with her… it probably means I’m gay.”
Both remember their days together as a very happy time in their lives and wish each other the best. Besides, both found their true love in the end, as Taylor married Ben Stiller, and Harris married David Burka.
#27. Matthew Perry and Julia Roberts
Everyone remembers the iconic Friends episode guest-starring Julia Roberts where she plays an old schoolmate of Chandler‘s (Matthew Perry) who makes him fall in love with her, only to get her revenge against him for making fun of her when they were little. But did you know that these two were actually dating back then? The pair met on the set of the show in 1996 and were spotted together after that.
Although he played an awkward, unlucky guy who’s absolutely terrified of commitment on the show, Matthew Perry is quite the ladies’ man and dated a bunch of celebs, especially back in the day (Meg Ryan, for example). So it’s really no surprise that he wooed Mrs. Roberts. Unfortunately, however, their relationship was never too serious and only lasted several dates throughout the year. Perry struggled with his addiction to drugs and alcohol, and couldn’t really keep up with a serious relationship. On her part, Roberts quickly moved on and dated Law and Order star Benjamin Bratt afterward.
#26. Ryan Reynolds and Kristen Johnston
Before marrying Blake Lively in 2012, Ryan Reynolds dated his fair share of celebrities. He famously dated Alanis Morisette and was married to Scarlett Johanson for two years. But one of the lucky ladies that dated the Canadian superstar is often forgotten. When he was just starting to get famous in Hollywood, he dated 3rd Rock from the Sun funny-woman Kristen Johnston. Their love affair began in 1999, and the pair made a few public appearances together.
They made their relationship public when they attended the premiere of The Green Mile together and were spotted out and about until 2000. Sadly, the pair broke up after just one year together, but the breakup was reportedly amicable and there are no hard feelings between the exes. Nowadays, Kristen Johnston is enjoying her life as a single woman, while Reynolds has two kids with wife Blake Lively.
#25. Richard Gere and Cindy Crawford
Richard Gere and Cindy Crawford actually go way back. What these two had was a romance built for the tabloids, and the public was absolutely crazy about them. They met in 1988 when Crawford was just 22 and Gere was 39. Soon, they became Hollywood’s hottest couple and appeared on several red carpets, magazine covers, and paparazzi shots. The stunning couple dated for three years and decided to tie the knot on December 12, 1991. But their wedding was even more fitting for a movie.
The couple hopped on a private jet and eloped to Las Vegas to get married. Their wedding was so spontaneous, that they didn’t even have rings and just wrapped aluminum foil around their fingers. Sadly, their intense romance came to an end when they announced their divorce in 1995. There has been a lot of speculation as to why they broke up, but eventually, Crawford admitted that it was the age gap between them that did the trick.
#24. Gary Oldman and Uma Thurman
Gary Oldman has had a crazy, intense, and scandalous love life. He had a total of five wives, and none of those marriages ended well. But what many seem to forget is that one of those wives was none other than Uma Thurman —his second wife, in fact. They met in 1990 when he was 30 and she was 20, but they didn’t seem to mind the age difference. Actually, they had a very passionate romance that grew extremely fast.
They started living together almost immediately, and by October of that same year, they got married. But their union didn’t last very long, and they got divorced 11 months later. Reportedly, Thurman dumped him via a letter, because she just couldn’t stand him anymore. She said it was impossible to live with him, due to his difficult character and his addiction to alcohol. And she’s not the only of his ex-wives who’ve stated the same. When asked about her failed marriage to Oldman, Thurman responded:
“It takes a special kind of woman to put up with him.”
#23. Lance Bass and Danielle Fishel
Danielle Fishel, known for playing Topanga in Boy Meets World, actually dated NSYNC‘s Lance Bass in 1998. Just as it happened with Neil Patrick Harris, Lance Bass was in the closet at the time, and dated women to throw people off from finding out he was actually homosexual. The pair met while taping a TGIF live special, where Bass attempted to get her phone number, but Fishel actually rejected him. Bass requested bandmate Justin Timberlake‘s help to get her phone number, and Fishel gave in.
They enjoyed a happy, teenage relationship until Bass broke up with Fishel out of nowhere. She was distraught, as she had no idea why he left her, but her mother actually suggested: “do you think there’s any possibility that Lance is gay?“, which turned out to be true. Once he came out of the closet, they became best friends and have been super close ever since. They remember their relationship as a funny anecdote now.
#22. Chris O’Donnell and Reese Witherspoon
Oscar-winner Reese Witherspoon was just beginning her career in the early 1990s. She was barely 16 years old when she stepped into the Hollywood scene hand-in-hand with actor Chris O’Donnell in February 1993. The fresh-faced teens paraded their young love along the red carpet at a tribute party for Al Pacino, who co-starred with O’Donnell in Scent of a Woman. The two love birds were all over each other and just couldn’t stop smiling, but that didn’t last long, unfortunately.
Their romance was exceptionally brief, as it lasted exactly one month. But that one month was very intense for the couple, and the media sure loved it. Sadly, the six-year age difference between the two got in the way of their relationship. Although six years don’t seem like much, it is especially tricky at such a young age. 22-year-old O’Donnell wasn’t on the same page as the teen actress, which caused them to fall apart. He found the love of his life shortly after, Caroline Fentress, who he’s still married to today, and Reese married Ryan Phillippe a couple of years later.
#21. Ellen Degeneres and Anne Heche
Legendary comedian Ellen Degeneres spent a good part of her career in the closet until she decided to let the world know she was gay in 1997. She graced the cover of Time Magazine that year with the caption “Yep, I’m gay“, which will certainly go down in history, and shortly thereafter she was seen dating women publicly for the first time. The first lucky lady she was involved with publicly was actress Anne Heche, who was eleven years her junior. The two had a very intense and public romance, often seen together in public holding hands, doing interviews, and even finishing each other’s sentences.
They quickly moved in together to a beautiful $3 million mansion in L.A. and opened the doors to their home for everyone to see. Their romance was so strong, that Ellen even said:
“If Anne goes, I want to go. That’s how strongly I feel”.
Sadly, they were together for a total of three and a half years before they broke up in 2000. They allegedly had an amicable breakup and wished each other nothing but the best.
#20. Matt Damon and Minnie Driver
Matt Damon made his big break in Hollywood in 1998 when Good Will Hunting came out. Not only did he star in the movie, but he also wrote the screenplay, which got him an Oscar. He was at the peak of his career and his face was in every single magazine out there. But he wasn’t alone. In fact, he was dating actress Minnie Driver, who he met on the set of Good Will Hunting, and the two quickly became the it couple at the time. Actually, to say that they were the it couple is an understatement; they were basically untouchable.
The fairytale romance, however, wasn’t what it appeared to be, and Damon wasn’t very happy in the relationship. So, what does someone do when they’re not happy in a relationship? Well, they break up with their significant other. Most people would do that in private, but Damon chose to actually do it on national television, and without even talking to Driver first. During an appearance on Oprah, he declared he was single, which not only surprised the public but also Driver. That’s why Damon should have also won the Oscar for the messiest breakup ever.
#19. Leonardo DiCaprio and Liv Tyler
The legendary Leonardo DiCaprio has broken his fair share of hearts over the years. He famously dated supermodels Gisele Bundchen, Bar Refaeli, and Naomi Campbell, among others, and was also linked to other superstars like Rihanna and Blake Lively. But one of his many flings was with Lord of the Rings actress Liv Tyler during the ’90s. But how did this unlikely couple meet? Well, Tyler appeared on Woody Allen‘s Everyone Says I Love You with DiCaprio’s best friend, Lukas Haas.
Haas set the two up, and they quickly began a passionate but brief romance. They were seen together at a party for the first and last time together. Although they never actually spoke about their hookup, the pictures suggested he Walked That Way with the model-actress daughter of Aerosmith frontman Steven Tyler. What can we say? He just can’t help dating supermodels!
#18. Owen Wilson and Sheryl Crow
Talking about odd pairs, one of the ’90s most unlikely couples were actor Owen Wilson and country singer Sheryl Crow. She was coupled up with Wilson from 1999 to 2001, and they even attended the exclusive Vanity Fair Oscar party together in 2000. The two met on the set of The Minus Man and were inseparable for three years. They were so close, that the duo even made music together. But their romance didn’t stand the test of time, and Wilson allegedly dumped her out of the blue, which prompted Crow to write several breakup ballads.
Although it didn’t end well, it at least gave Crow some inspiration for her music. She got back on her feet very quickly, however, and started dating cyclist Lance Armstrong. Her relationship with Armstrong was pretty messy, and the two actually broke up a couple of weeks before their wedding. Interestingly enough, she did remain friends with Wilson, and the two are still close to this day.
#17. Notorious B.I.G. and Faith Evans
Legendary rapper Notorious B.I.G. dated R&B singer Faith Evans during the ’90s, and the two had a very special but tumultuous relationship. They started off very quickly, and just couldn’t get their hands off each other after meeting on the set of a Bad Boy Records photo shoot, the label they both belonged to. Just after eight days of dating, the two eloped and tied the knot But, just as quickly as it started, it ended. The couple filed for divorce just a few months after their wedding.
In an interview with Vibe magazine, Biggie said;
“I married her after knowing her eight days and I was happy. That was my baby. At the same time, with us being so spontaneous, we did it backwards. Maybe she won’t admit it, but I will. We should have got to know each other and then got married. The relationship kind of dissolved, but we’re still going to be friends.”
Unfortunately, the pair didn’t get to make amends, as Biggie was murdered in 1997.
#16. Ashton Kutcher and January Jones
Before Ashton Kutcher left his mark on Hollywood and married Demi Moore, he went out with January Jones, who was also a beginner in the film industry. The two met at the start of their careers when they were struggling actors trying to get just one callback. According to Jones, however, the relationship wasn’t a positive one, and it actually was an obstacle on her path to becoming an actress. Although she was reluctant to give away his name at first, she did talk about the ill-fated relationship during an interview:
“The guy I was dating when I first got to L.A. was not supportive of my acting. He was like, ‘I don’t think you’re going to be good at this”. if anything, I should thank him. Because the minute you tell me I can’t do something, that’s when I’m most motivated.”
Although she’s said she holds no grudge against Kutcher, when she was asked to send a message to him, she refused. On his part, Kutcher never made any comments about their relationship.
#15. David Spade and Kristy Swanson
If there is one guy in this world with an impressive dating record, that guy is definitely David Spade. If he put all his ex-girlfriends on a ship, it would sink immediately. He has dated, among others, Carmen Electra, Tara Reid, and Pamela Anderson. But the first one that started it all was none other than actress Kristy Swanson. The two were fresh faces in the Hollywood scene and were seen together out and about many times. Funny enough, the couple always denied they were ever together, even though they were photographed walking hand-in-hand a gazillion times.
The two had a brief relationship from 1996 to 1997, but their breakup was amicable. in fact, they have remained friends all this time, which proves you can totally be friends with your ex. Recently, Swanson tweeted:
“I love @DavidSpade he’s quite the romantic I must say & my favorite skinny/fat guy”
#14. Joaquin Phoenix and Liv Tyler
Joaquin Phoenix found his first love in Liv Tyler when they were both just 18 years old. They met in 1995 when they began their sweet relationship that lasted a little over three years. During that time, they starred in 1997’s Inventing the Abbotts and were seen together multiple times. Although they eventually separated, they had a very friendly breakup and are still friends nowadays. In fact, Tyler is still friends with his whole family; she’s very close with his sisters and with Joaquin himself.
When asked about Liv, Joaquin said:
“She’s a darling. I’ve said it over and over again. When Liv and I met, it was for a reason —I really needed her and she really needed me.”
On her part, Tyler explained:
“I’m friends with all my exes! I love them so much! I consider Joaquin and all of his sisters to be like family. We were so young when we were together, like 18 to 21. He was my first love.”
#13. Luke Wilson and Drew Barrymore
You can’t think about the ’90s without thinking of Drew Barrymore. At that time, Barrymore was at the front of every project imaginable, and her then-boyfriend, Luke Wilson, was also breaking hearts on the big screen. The two met on the set of Home Fries in 1997, where they began their relationship. They were mad for each other for over two years, but it all came to an end in 1999. However, as both are very professional actors, they didn’t let their breakup get in the way of their careers, and actually starred in a movie together post-split.
Right after their breakup, filming of Charlie’s Angels began, where Barrymore played one of the angels alongside Cameron Diaz and Lucy Liu. Wilson was also in the movie playing Cameron Diaz’s love interest. That must’ve been awkward, considering Barrymore and Diaz were super close friends, right? Truth is, not at all. The three of them kept things totally professional the whole time, and the movie was a huge success and actually spawned a sequel.
#12. Paul Thomas Anderson and Fiona Apple
Musician Fiona Apple famously dated six-time Oscar nominee Paul Thomas Anderson during the ’90s, earning the title of the “coolest, dorkiest, sexiest, and most indelible celebrity power couple of the ’90s,” as stated at the time. These two were completely adorable together and spend all day and night all over each other. They were often seen out an about and on the red carpet, always smiling and holding hands. But they also mixed business with pleasure.
They collaborated artistically during their joint rise to fame; he directed a number of her music videos, including Across the Universe, Fast as You Can, Limp, and Paper Bag. Sadly, they broke up in 2000 but remained friends since then. They reunited a decade later when Anderson directed Apple’s music video for Hot Knife. Paul is now married to SNL alum Maya Rudolph, and Paper Bag was even featured in Maya’s hit comedy Bridesmaids in 2011.
#11. Emilio Estevez and Paula Abdul
Actor Emilio Estevez, brother of Charlie Sheen, dated American Idol judge Paula Abdul for three years, starting in 1991. Their romance grew very quickly, and they were so madly in love that they decided to get married just a year later after they started dating in 1992. Abdul actually released a single called Will You Marry Me? to declare her love for Estevez, and he said yes right away. It sounded like the perfect recipe for a love that would last forever but sadly, it didn’t.
On May 10, 1994, after two years of marriage, Abdul filed for divorce, citing irreconcilable differences. She later explained that she wanted to have kids with Estevez, but he didn’t. He already had two kids of his own from a different marriage and just didn’t want to bring more into this world. The problem was, however, that Estevez did not disclose that to Abdul until after they were married, which felt like a slap in the face for Abdul.
”It was very hard for him to admit that he couldn’t handle having kids again,” Abdul said. ”It was heartbreaking for us both.”
#10. David Copperfield and Claudia Schiffer
David Copperfield marveled audiences with his incredible illusions, but the biggest magic trick he ever pulled was getting Claudia Schiffer to date him. They met at a gala in 1993 when he brought her up on stage to participate in a mind-reading act and flying illusion. Just a year after they started dating, the couple got engaged. Everything seemed to be going right between the supermodel and the magician, and they were seen on many red carpets and public events together.
The odd couple sparked many comments, especially because of the 14-year age difference between them, to the point where Paris Match actually published an article claiming their relationship was only for publicity. The couple quickly sued the magazine in 1997 and won. Sadly, however, they separated two years later. Reportedly, the breakup was amicable, and they both found their true loves shortly after their split.
#9. Ted Danson and Whoopi Goldberg
Many people have forgotten that these two were actually a thing back in the day. The weird relationship between Whoopi Goldberg and Ted Danson occurred during the peaks of their respective careers: Ted still had Cheersgoing strong and Whoopi had recently won an Oscar for Ghost. Their involvement, however, was more of a scandal than anything else. Danson met Goldberg on the set of Made in America but was actually married at that time, and that’s why everything went south.
The two had an affair that was eventually discovered by the public, costing Danson his marriage and also his fortune. Danson and his then-wife went through a very public divorce that took two years to be finalized. He ended up paying his ex-wife $30 million, making it one of the most expensive divorces ever at the time. After the tumultuous divorce, the couple didn’t last very long, and they separated after five years together in 1993.
#8. David Arquette and Alyssa Milano
Before either of their careers had garnered any acclaim, actors David Arquette and Alyssa Milano began dating. The two became an item in 1991 and became quite the couple. They were spotted together for the first time at the Bill & Ted’s Bogus Journey Party and several times thereafter, smiling and holding each other. They weren’t very famous at the time, but the public surely loved them. They were each other’s first love, as Arquette was 20 and Milano 19 years old when they met.
Sadly, their teenage romance didn’t last long. In fact, it barely lasted one year, which is such a shame considering they looked so cute together. After their breakup, Milano hit it big when she starred in Charmed, and Arquette became a household name when he starred in Scream, where he met his then-future-wife Courteney Cox in 1995. On Milano’s part, she went on to date stars such as Justin Timberlake and eventually settled down with Dave Bugliari, who she married in 2009.
#7. Michael Keaton and Courteney Cox
Before dating David Arquette and famously changing her last name to Cox-Arquette, Friends star Courteney Cox dated Batman star Michael Keaton, and the two had a very high-profile relationship. The couple met in 1989, long before Cox had her big break in 1994. Back then, Keaton had already cemented his career as a film actor, but Cox was just starting to get her name out there. The two dated for six years before Cox decided to end the relationship.
Allegedly, the two weren’t on the same page, perhaps due to their age difference —Keaton was 44 and Cox was 31. Also, Keaton didn’t want to settle down and have children, and that’s what she wanted all along. They had a friendly breakup, however, and Cox told People:
“It’s the most important relationship I’ve ever had, and I think he’s the most wonderful person I’ve ever met.”
#6. Edward Norton and Drew Barrymore
Everyone Says I Love You is a 1996 American musical comedy film written and directed by Woody Allen, who also stars alongside Edward Norton and Drew Barrymore. It was during the filming of this movie that Norton and Barrymore began their brief but passionate relationship. The two showed up hand-in-hand to the premiere and were seen several times together after that. They made such a cute couple, didn’t they? But unfortunately, it just didn’t last.
The two always denied rumors that they were together even though they were spotted hanging out several times. But, when Barrymore was seen dating Luke Wilson in 1998, it was clear that it was over with Norton. Also, Norton began dating musician Courtney Love, who he dated for two years and even proposed to. Sadly, the marriage never happened, and the two moved on. The ’90s weren’t very lucky years for Norton in the love department.
#5. Spike Jonze and Sofia Coppola
Filmmaker Spike Jonze and director Sofia Coppola were definitely a power couple in the ’90s. The two met in 1992 on the set of Sonic Youth’s music video for 100%, which Jonze was asked to direct, and they were inseparable since then. They dated for several years and finally got married in 1998. They enjoyed four happy years as a married couple and, to the surprise of everyone, got divorced in 2003, citing irreconcilable differences.
They both shared their passion for filmmaking and were said to inspire many of each other’s works, even after they got divorced. the two most emotionally-charged films of both directors’ careers —Lost in Translation and Her— were among their first projects released post-divorce, and are believed to be representations of their failed marriage. The main character of Lost in Translation was reportedly based on Jonze. It was that movie that got Coppola the Oscars for best director, best original screenplay, and best movie.
#4. Carson Daly and Jennifer Love Hewitt
Television host Carson Daly and actress Jennifer Love Hewitt were together in the ’90s, and reportedly had one of the most awkward relationships in the history of celebrity couples. They began dating in 1998, when Hewitt was the teen movie, queen, starring in I Know What You Did Last Summer and Can’t Hardly Wait, and Daly was driving teenagers crazy as a VJ in MTV‘s TRL. The two were so deeply in love, that Daly actually got a tattoo of Hewitt on his leg. So what went wrong?
Allegedly, Daly had no idea that Hewitt was unhappy in the relationship and was planning on breaking up with him. Then, he found out the hard way, as Hewitt opened up about her relationship troubles in an interview with Howard Stern in his radio show, and actually announced they were breaking up live on air. The pair later had several awkward encounters, as they handled the same social circles. It wasn’t until 2005 that the exes buried the hatchet when Daly invited Hewitt to his talk show.
#3. Vanilla Ice and Madonna
The queen of pop had many public relationships over the years, but the most bizarre one was with infamous rapper-turned-reality-star Vanilla Ice. Their relationship had everyone asking: when, how, and why? But the truth is that they had a very intense and serious relationship in 1992 that lasted a total of eight months. The relationship was reportedly doing great until Madonna released a book called Sex, which marked the end of their relationship.
Vanilla Ice explained to the public that, when Madonna’s book came out, he didn’t like it at all. It was very sexual and contained pictures of the queen of pop naked, which didn’t sit well with Ice, who broke up with her because of that. Not only that, but the book contained pictures of Vanilla Ice, without his consent, which only made things worse. He said:
‘When the book came out I was so embarrassed and ashamed. It was a porno.”
#2. Matt Dillon and Cameron Diaz
Cameron Diaz was at the peak of her career when There’s Something About Mary was released in 1995. She also happened to meet her then-boyfriend Matt Dillion on the set of the movie. The two dated for a total of three years, until their split in 1998. Although they were madly in love, they couldn’t make the relationship work, because Dillon wanted to settle down and have children, and Diaz wanted the opposite. Children were never in Diaz’s plan; fast forward to today, and she still feels the same way.
When asked about the breakup, Dillon told Parade:
“I fell in love. It’s a very powerful thing when you feel that way about somebody. Cameron was a muse for me. I hadn’t been in any deep emotional relationships.You fall in love, and all that passion goes into procreating and wanting children. I’ve felt that need to want to raise a child”
#1. Nicole Kidman and Tom Cruise
We all remember those days when superstar Tom Cruise was jumping on Oprah‘s couch screaming “I love Katie Holmes!“. But many seem to forget that before Holmes, Cruise was married to Australian actress Nicole Kidman. Perhaps, it’s because both of them refuse to talk about their failed marriage to this day. The truth is that the two young stars met in 1990 on a movie set and tied the knot right away. They were both leaving their mark in Hollywood, and the public was crazy about them.
During their marriage, the couple adopted two children, Connor and Isabella. They were happily married for almost 11 years, until Cruise filed for divorce in 2001 and got custody of the two children, which took Kidman by surprise. She was happy in the relationship and definitely did not see the divorce coming, as she said in an interview:
“Our life together was perfect. It took me a very long time to heal. It was a shock to my system. That was a great relationship. I think it ran its course. I was really damaged and not sure whether [love and marriage]was ever going to happen again to me.”