True love is hard to find. Many relationships stay in the halcyon honeymoon phase for months or even years, only to fall apart further down the line. Others are doomed right from the beginning, with everyone around them wondering what on Earth they could be thinking. However, as hard as it is for normal people to make a love connection, it’s even harder for celebrities to have a successful dating life. Not only are there constant rumours and press attention, but new celebrity couples can’t even go out for dinner without being caught by the paparazzi.
The reason we’re so fascinated by celebrity couples is simple: they’re aspirational. Not only do they tend to be rich and famous, but we plaster them on magazines because they’re also some of the most beautiful people in the world. The question is, out of all of the famous couples in the world – both the successful and the not so successful – who are the most gorgeous of them all? Below are what we believe to be the most beautiful celebrity couples of all time, and whilst not all of their relationships stood the test of time, we think you’ll agree that they all look absolutely perfect!
20. Brad Pitt and Gwyneth Paltrow
If the term ‘blonde bombshell’ could ever be applied to a couple rather than an individual, then it surely fits the bill for Brad Pitt and Gwyneth Paltrow.
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Brad Pitt exploded onto everyone’s screens as the rough and tumble cowboy hitchhiker in 1991’s Thelma and Louise, while Gwenyth Paltrow began her career playing a young Wendy Darling in Steven Spielberg’s fantasy adventure Hook.
The two met relatively early in their respective careers, having both worked on the 1995 crime thriller Se7en. Pitt and Paltrow played spouses in the picture, with Paltrow playing the wife of Pitt’s young detective David Mills.
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The pair quickly fell in love and began a whirlwind relationship that lasted from the year 1994 to 1997. They even got engaged, but called off the wedding when Gwenyth Paltrow confessed that at the of age 24, she did not feel ready to get married.
The two broke it off not long after, and Gwenyth Paltrow later said that the experience of having such a high-profile relationship taught her a lot about privacy and discretion, as well as the need to keep her love life separate from her career.
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This revelation affected Paltrow so much that when she began dating fellow actor Ben Affleck a few months after breaking up with Brad Pitt, she went to much greater lengths to keep the details private.
19. Britney Spears and Justin Timberlake
When it comes to predicting relationships that would turn out to be fraught with drama, Britney Spears and Justin Timberlake’s was not near the top of anyone’s list.
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As two members of the All-New Mickey Mouse Club, as well as kind of high school sweethearts (since they both went to high school virtually, and got their diplomas from the same place) it seemed as though the pair were about as wholesome as it was possible to be.
Justin Timberlake first made a move in 1999, and it wasn’t long before the couple debuted themselves on the red carpet. Over the course of their relationship, they made the front page with several iconic fashion moments, including the now infamous all-denim looks.
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Unfortunately, the love between these baby faced stars was not built to last. Spears and Timberlake abruptly broke up in 2002, with Timberlake releasing his hit song Cry Me a River not long after. The music video featured a blonde woman who looked like Spears, sparking rumours that she had been unfaithful to him during their relationship.
It’s unlikely that the pair will ever get their friendship back to where it once was, but Justin Timberlake did make headlines this year, when he released an apology message dedicated to both Spears and Janet Jackson.
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In the message, Timberlake said that he “should have done more” to protect Britney Spears from the cruel way the media treated her, even after they had broken up.
18. River Phoenix and Martha Plimpton
Many celebrity couples have at one point or another been in the running for the most beautiful couple in Hollywood Award. However, none made waves quite so early in their careers as River Phoenix and Martha Plimpton.
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The pair got together in 1986, when both Phoenix and Plimpton were just sixteen years old. They met just before beginning work on Running on Empty together.
In Running on Empty, the pair played each other’s first loves. River Phoenix played Danny Pope, the son of two anti-war activists who are on the run from the police. Martha Plimpton played Lorna Phillips, the daughter of the piano teacher determined to give Danny a better life.
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Much of Phoenix’s character in the film reflected his real-life upbringing, as he too moved around a lot as a child. His parents lived in various communes around the country, and eventually joined the Children of God, which meant that Phoenix grew up having never gone to school.
The relationship between Phoenix and Plimpton only lasted into their late teen years, as by 1989 they had grown apart and split up. In one famous incident, Phoenix ran out of a restaurant after Plimpton ordered seafood, because he was a passionate vegan and animal activist.
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Speaking about Phoenix after his death at the age of just 23, Plimpton said: “He was just a boy. A very good-hearted boy who was very f***ed up and had no idea how to implement his good intentions.”
17. Johnny Depp and Winona Ryder
The relationship between Winona Ryder and Johnny Depp was the definition of tumultuous young love. The pair met at the premiere of Great Balls of Fire in June of 1989 and began dating just two months later, when Depp was 26 and Ryder was 17.
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Sparks flew immediately and the bond they had was deep, with Ryder saying: “Johnny was my first everything. My first real kiss. My first real boyfriend. My first fiancé. The first guy I had sex with. So he’ll always be in my heart. Forever. Kind of funny that word.”
Most well known is the fact that the pair collaborated on Tim Burton’s 1991 classic Edward Scissorhands. Both Ryder and Depp developed a love for both Burton and his oddball aesthetic, with Ryder starring in his 1988 project Beetlejuice, and Depp returning to work with him on 1994’s Ed Wood.
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Ryder’s love of quasi-gothic and edgy projects extended beyond her work with Tim Burton, as she also starred in Francis Ford Coppola’s grand horror romance Bram Stoker’s Dracula, as well as the dark teen comedy Heathers.
Winona Ryder and Johnny Depp’s relationship sadly did not last, with the pair getting engaged in July 1990, but splitting up in 1993. In response, Depp famously had to have his “Winona Forever” tattoo amended, to instead say “Wino Forever”.
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Since their decade-defining split, Johnny Depp has had several high-profile relationships, from model Kate Moss to actress Amber Heard. Winona Ryder dated Soul Asylum member Dave Pirner immediately after her split from Depp, but has been steadily dating Scott Mackinlay Hahn since 2011.
16. Ethan Hawke and Uma Thurman
It’s hard to think of a more sombre and striking looking couple than Uma Thurman and Ethan Hawke. Both actors have been in their fair share of gritty projects, with Thurman starring in Pulp Fiction and Kill Bill, and Hawke appearing in horror movies like Sinister and The Purge.
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Despite their serious veneer, the couple’s relationship was filled with joy and laughter, all the way from its beginning in 1998 to its end in 2003.
The pair met on the set of the 1997 sci-fi dystopia Gattaca, and struck up a romance almost immediately. The pair were married less than a year later, on the first of May 1998.
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Uma Thurman had been married and divorced once before, having finalised her separation from Gary Oldman in 1992. For Ethan Hawke, this represented his first serious relationship, and he even went so far as to dedicated his second book to Thurman.
After their break-up in 2003, Ethan Hawke began dating Ryan Shawhughes, who he eventually married in 2008. Shawhughes had worked as a nanny to Hawke and Thurman’s children previously, but Hawke denied that anything had happened between them at the time.
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Speaking about his relationship to Shawhughes, Hawke said in an interview: “My [first] marriage disintegrated due to many pressures, none of which were remotely connected to Ryan.”
15. Bruce Willis and Demi Moore
Bruce Willis is one of the biggest names in Hollywood, so it’s difficult to imagine him ever feeling shy or self-conscious. However, when Willis first met actress Demi Moore, he allegedly turned into a bundle of nerves.
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The pair met at a premiere party for the 1987 movie Stakeout. Willis stared at Moore all night, so much so that even Moore’s ex-boyfriend Emilio Estevez noticed. Eventually, Willis found the courage to buy Moore a drink, but was so anxious that “his hands were shaking”.
From that moment, Moore and Willis seemed to have the ideal Hollywood romance. Moore later said of the night: “Bruce was so gallant- in his own boisterous way, a real gentleman. When I said it was time for me to go home, he offered to walk me to my car. He was so eager about it – like a little boy who didn’t want to miss the ice-cream truck.”
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She went on to say: “When he asked for my number, I felt a wave of schoolgirl flutters.”
The pair married in 1987, and had a daughter together, but there were soon rumours of trouble in paradise. It later conspired that the pair were too successful for their own good, resulting in clashes about who should take on what role as parents.
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Moore later said of their divorce in 2000: “It was as if he woke up a few years later and thought, ‘Whoa, is this what I want? Or do I really want to be free?’ I think he was struggling to resolve a conflict within himself: he wanted family and grounding, but he also craved excitement and novelty.”
14. Will Smith and Jada Pinkett Smith
Will Smith and Jada Pinkett Smith have been a Hollywood institution for decades. The pair have been an item ever since they met on the set of The Fresh Prince of Bel-Air when Jada auditioned for the role of Will Smith’s girlfriend.
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Pinkett might have been knocked back for the role on the grounds that she was too short, but the pair definitely didn’t have to fake any chemistry for the cameras, as it didn’t take long for them to fall for each other for real.
According to rumours, Will Smith called Jada Pinkett sometime after the audition and asked her if she was seeing anyone. When she said no, Smith smoothly replied “Cool, you’re seeing me now” and the rest is history.
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The pair were married in 1997, in a ceremony attended by just 100 people. They have been married ever since, though they briefly separated before reuniting around 2016. During that time, Pinkett admitted to having an affair with the singer August Alsina, calling it an “entanglement” that Smith was aware of.
Despite bumps in the road, both Will Smith and Jada Pinkett Smith have made it clear that they are in the relationship for the long haul. Speaking about their relationship, Pinkett Smith once said in an interview: “I will throw my career away before I let it break up our marriage. I made it clear to Will. I’d throw it away completely.”
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The pair have two children together, Jaden and Willow Smith. Both are already immensely successful in their own right, making careers for themselves in acting, modelling and music.
13. Michael Hutchence and Kylie Minogue
Throughout the mid and late 80s, the media were convinced that Kylie Minogue and Jason Donovan’s relationship would last forever. The pairing of the pop princess and the soap star seemed like it could not be more perfect, so everyone was shocked when Minogue ended it in 1989.
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While Donovan has since said that “It was an extremely painful parting of the ways and, without doubt, I took a long time to recover from it,” Minogue herself moved on pretty quickly, since she began dating Michael Hutchence immediately afterwards.
Michael Hutchence was the frontman of INXS, one of the biggest bands in the world at the time, and he was also known as the “wild man of rock”, thanks to his reputation for public brawling and substance abuse.
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Many were shocked that Kylie Minogue had left the wholesome Jason Donovan for Hutchence, with Donovan himself saying: “It was bad enough that she’d run off with anybody, but she happened to run into the arms of the greatest rock god of the period, the very guy who I secretly wanted to be. That was a pretty big punch to take.”
Minogue and Hutchence dated from 1989 to 1991, though they each spent much of that time touring. While apart, they would fax each other secret love letters, complete with secret nicknames and private code words.
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Hutchence tragically died in 1997, after dating and sharing a child with Paula Yates. In the years following the tragedy, Kylie Minogue began to keep her love life more private, though it was revealed in 2018 that she was dating Paul Solomons.
12. Ryan Gosling and Sandra Bullock
The relationship between actors Ryan Gosling and Sandra Bullock might have been brief, but that doesn’t mean that it didn’t make an impact.
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The pair dated from around 2002 to 2004, and were careful to keep their relationship secret at the time, but that did not stop the media from speculating every time a picture of the two together began circulating.
Many years after their love affair was already over, both Sandra Bullock and Ryan Gosling independently confirmed that they were indeed dating.
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According to them, the pair met while working on the film Murder By Numbers, in which Bullock plays a brilliant police detective determined to implicate Gosling’s character in a murder he orchestrated. While working together on the grisly movie, they struck up a relationship in secret.
Speaking about their relationship after the fact, Ryan Gosling said that his relationship with Sandra Bullock comprised some of his fondest memories and that she remained one of his “greatest girlfriends”, along with Rachel McAdams.
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In return, Sandra Bullock said that she was grateful to Ryan Gosling for helping her to become more “chill”. She also said that she maintained that the two of them were only “friends” at the time in order to be politically correct, due to the 16 year age gap between them.
11. Lisa Bonet and Lenny Kravitz
It is said that opposites usually attract, but that wasn’t the case for actress Lisa Bonet and musician Lenny Kravitz. Instead, the couple bonded over their considerable similarities, which surprised them both.
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The two became fast friends after meeting in 1987, and they eloped and got married in the same year. Bonet theorised in an interview that she was willing to move so fast because of their similarities, saying: “When I first told him my mom was Jewish, and he said ‘So’s my dad,’ I thought that was both unusual and enchanting. And I think I trusted him a little more with my feelings and let him inside a little more than I ordinarily would have.”
Lenny Kravitz was as instantly enamoured with Lisa Bonet as she was with him, again because of how remarkably similar he thought they were. Speaking in an interview, he said: “She was like a female version of me. That woman inspired me so much. It was a magical time that she and I shared. I just opened up artistically.”
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Unfortunately, the pair were perhaps too much alike. Bonet broke the relationship off in 1993, after a number of deaths in her family made her feel as though she had moved too fast into something too intense. Kravitz took the breakup hard, saying: “I was in a tremendous amount of pain when we broke up, tremendous. For, like, six months, I only slept for two hours a day, from 4 a.m. to 6 a.m.”
Thankfully, the pair are on much better terms now. Lisa Bonet went on to marry actor Jason Mamoa in 2017, and both she and her new husband are very close with Lenny Kravitz. In fact, Bonet and Momoa’s children even call Kravitz “Uncle Lenny”.
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Speaking about their new arrangement, Kravitz said: “We are one family unit. We have a child, and we love each other just as much as before – it’s just a different situation. I love her husband, and I love her children. We all get together, and we have the best times.”
10. Kurt Russell and Goldie Hawn
As the tabloids remind us every day, as glamourous as Hollywood romances look, they don’t always work out. However, there are rare exceptions to the constant cycle of breakups and makeups in the world of celebrity dating, and a great example is Kurt Russell and Goldie Hawn.
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Russell and Hawn are happily dating and have been continuously ever since Valentine’s Day 1983. That means the pair have been together for 38 years, and they’re still as sappily devoted to each other as they always were!
It may come as a surprise to some that Hawn and Russell have never been married, and they have zero plans to tie the knot any time soon. Hawn once said that she “would have been long divorced if I’d been married [to Russell]” and that neither she nor Russell believes that marriage helps to cement a relationship.
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Hawn has been married in the past though, as she previously walked down the aisle to Gus Trikonis, the dancer and director most famous for playing Shark in West Side Story. After divorcing him in 1973, Hawn then married musician Bill Hudson of the Hudson Brothers in 1976, and the pair had two children together – son Oliver, and daughter Kate.
Goldie Hawn and Kurt Russell first met in 1966, while working together on the Disney live-action musical The One and Only, Genuine, Original Family Band. Though they were taken with each other at the time, nothing came of it until 20 years later, as they were both seeing other people.
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The One and Only, Genuine, Original Family Band was not the only project they would go on to appear in together, as they briefly shared the screen again in 2018’s The Christmas Chronicles when Hawn cameoed as the Mrs Clause to Russell’s Santa. Hawn’s performance was so good that the part was expanded, resulting in there being far more of her in 2020’s The Christmas Chronicles 2.
9. Kevin Bacon and Kyra Sedgwick
Kevin Bacon and Kyra Sedgwick’s relationship is another love story that has stood the test of time. The pair met on the set of the 1988 PBS movie Lemon Sky, and were instantly smitten with each other, so much so that they were married that same year.
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The pair went on to have two children: Travis Bacon, who was born in 1989 and Sosie Bacon, who was born in 1992. Not only that, but they are still happily married today, with a marriage that is going on 33 years strong!
Over the years, the pair have taken turn letting their career take the backseat, in order to have equal chances to raise their children and pursue their acting goals. Speaking about the delegation, Bacon said: “She’s made a lot more sacrifices than I’ve made. Kyra felt really strongly that, when she started to have children, she needed to be there for them.”
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However, Sedgewick did get her chance to return to the small screen when their children got a little older, as Kevin also clarified. “When The Closer came along—I don’t even look at this as a sacrifice—but the kids were still in high school or junior high and she had this opportunity to go out to California and to be a lead in a TV show. I said, ‘Listen, I’ll stay with the kids.'”
The pair have put a lot of time and effort into keeping their marriage fresh, by taking up new hobbies like going skiing together, and even purchasing each other instruments in order to inject some excitement. However, they’ve also teamed to campaign on issues they’re passionate about, such as the environment.
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Bacon and Sedgwick hosted a letter-writing campaign at their house in order to encourage voters, and have campaigned on everything from protecting the oceans to animal conservation. They also work hard to reduce their own plastic use at home – how romantic!
8. Jennifer Lopez and Ben Affleck
All new celebrity romances make headlines in the beginning, but few have resulted in as much speculation, gossip and media attention as Jennifer Lopez and Ben Affleck’s relationship.
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When the pair went public in 2002, it was plastered across every celebrity magazine, with many wondering how the glamorous J-Lo had fallen for the laidback and casual Ben Affleck.
Rumours first began to swirl around the pair when they were on set together, filming the 2003 movie Gigli. However, many doubted the validity of stories about sparks between the two, since Lopez was married to Cris Judd at the time.
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That all changed when, less than seven months after her wedding to Judd, Lopez filed for divorce. Before the movie even came out, just a few short weeks after the divorce papers were filed, Lopez went public with her relationship to Affleck, sparking a media frenzy.
After two years together, Ben Affleck and Jennifer Lopez announced their engagement in 2004. Unfortunately, the huge celebrity wedding fans of the couple were expecting never came to be, as the pair called it quits before they could exchange vows.
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Not only that, but after the split, Jennifer Lopez got back together with her ex-boyfriend Marc Anthony, and they got married a few months later. Despite the break-up, Affleck has continued to praise and support Lopez publicly, even saying that she deserved an Oscar for her performance in Hustlers.
7. Winona Ryder and Matt Damon
Winona Ryder already appeared on this list thanks to her relationship with Johnny Depp, but that is not the only beautiful celebrity couple that she has been a part of. Later in her life, Ryder began dating fellow actor Matt Damon, and the two immediately captured the attention of the press.
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The pair dated at the tail end of the 90s, after being introduced to each other by Gwenyth Paltrow. Paltrow was dating Matt Damon’s best friend Ben Affleck at the time, and was good friends with Winona Ryder, since they had previously been roommates.
Ryder and Damon hit it off immediately and began dating almost straight away. The pair had an advantage in that their relationship flew under the radar for a while, because most people were convinced that Matt Damon was instead dating his Good Will Hunting co-star Minnie Driver.
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Despite their excellent chemistry and lowkey approach to their relationship, fame still put a strain on the couple that eventually caused them to break up. By 2004, it was all over.
Neither of them has ever come clean about exactly what caused the split, although Matt Damon insisted in an interview that it was nothing exciting or scandalous. Damon called what he had with Ryder a “great relationship” and said their flirtation “ended for reasons far more pedestrian than, say, a mad orgy at the Four Seasons [with] Richard Gere.”
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Dating Winona Ryder did change Matt Damon’s dating habits forever though. Nowadays, he only dates what he calls “civilians”: people not involved with Hollywood or the world of entertainment. Shortly after breaking up with Ryder, Damon admitted in an interview: “I don’t think I could fall in love with a celebrity right now, because it would mean changing my lifestyle, and I like that my lifestyle feels normal to me most of the time,”
6. Julia Roberts and Jason Patric
Julia Roberts and Jason Patric’s relationship got off to a pretty unorthodox start. Roberts was all set to marry fellow actor Kiefer Sutherland on the 11th of June 1991, but she called off the engagement three days before the wedding, in a move that shocked the press.
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Not only did Roberts cancel her wedding to begin dating Jason Patric, but Patric and Sutherland were fast friends at the time, making the story even more scandalous.
Keifer Sutherland and Julia Roberts met on the set of Flatliners in April 1990, and it didn’t take them long to take their relationship public. They got engaged within a year, making it Roberts second engagement, as she had previously announced her intention to marry Dylan McDermott.
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Jason Patric emerged into this complicated picture and whisked Roberts away on a romantic trip to Ireland, where they began dating. Unfortunately, even the stunning vistas of Ireland could not keep this gorgeous couple contented for long, as they split up in early 1992.
Julia Roberts went on to marry the country singer Lyle Lovett in 1993, and split up with him two years later in 1995. Her second marriage fared much better, as she has been happily married to Daniel Moder ever since 2002, and the pair even have three children together.
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As for Jason Patric, the Lost Boys star went on to date Danielle Schreiber for around ten years, until they separated in 2012. The pair conceived a son together using in vitro fertilization, resulting in Patric having to lobby the state of California to give sperm donors the same rights as fathers in order to access custody rights, once Patric and Schreiber broke up.
5. Richard Gere and Cindy Crawford
People have disagreed for years about who was the true supermodel face of the 90s, but everyone agrees that Cindy Crawford is at least in the running. At the age of just 22, Crawford had already graced the covers of over 300 magazines, and she was considered one of the most beautiful women in the world.
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So it was no surprise to anyone when in 1988, Crawford appeared on the arm of Richard Gere, an actor who had cemented his reputation as a Hollywood heartthrob after starring in American Gigolo. The pair met at a barbeque hosted by photographer Herb Ritts, and were enamoured with each other right away.
Despite their 17 year age difference, Gere and Crawford were together for six years, and were married for four. Despite Gere’s reluctance to tie the knot, the pair eventually married in a last-minute Las Vegas ceremony.
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According to the tabloids, Crawford wore a dark blue jumpsuit and married Gere before he flew out to a film set the next day. Since they had not planned to get married, there was no time to find rings, and so they fashioned some out of aluminium foil. How adorable!
Unfortunately, Hollywood’s most beautiful pairing was not destined to last, and the couple finalised their divorce in 1995. Crawford later said that as she grew up, she found herself thinking “I want to lead sometimes and I want to walk side by side sometimes”, which Gere was not used to.
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Crawford also blamed the fact that they were “never friends” for their eventual break-up, and said that friendship being the foundation was what made her new marriage to Rande Gerber more likely to last. True to her word, Crawford and Gerber have been married since 1998.
4. Jack Nicholson and Anjelica Huston
Very few celebrity romances have the drama and passion of Jack Nicholson and Anjelica Huston’s relationship, which remained a Hollywood staple for over 17 years.
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From 1973 to 1989, Nicholson and Huston had a relationship as intense as it was sporadic, with the tabloids watching as Nicholson balanced other affairs with his relationship with Huston, and Huston moved in and out of his house, attempting to follow her own career path.
The pair met at Nicholson’s birthday party, and Huston was so smitten that she moved into his house shortly after. However, Nicholson was already at the height of his fame, and had several people working at his home.
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This left Huston struggling to find a way to fit in. As she later said in an interview: “Those are the things that crop up when you move in with a man of certain notoriety. They’ve got people around to do stuff for them, so it’s not even as though I could fit into the role of housewife, or even flower arranger. There was no role, except to be on his arm.”
Nicholson constantly wooed Huston with outrageous gestures, even once allegedly buying her an elephant. Not only that, but even after they broke up, Nicholson gifted Huston a pearl and diamond bracelet that Frank Sinatra had previously given to Ava Gardner. The note said: “These pearls from your swine. With happiest wishes for the holidays—Enjoy—Yr Jack.”
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In the end, it was Nicholson’s infidelity that ended the relationship. When Nicholson revealed that his mistress Rebecca Broussard was pregnant, Huston said that he had an obligation to support the baby, and that she would step out of the picture. Huston did just that, and the great love affair of the 80s was over.
3. Tom Cruise and Nicole Kidman
Many celebrities have love lives that have been riddled with controversy and speculation over time, but none so much as Tom Cruise. It was once even reported that after he split up with Penelope Cruz, Cruise allowed the Church of Scientology to audition actresses to be his future spouse.
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In our hearts though, Cruise is still with the gorgeous Nicole Kidman, who met him on the set of Days of Thunder in 1989. The pair were married on Christmas Eve in 1990, and their marriage lasted all the way until the 8th of August 2001.
While together, Cruise and Kidman adopted two children: Isabella Jane Cruise, and Connor Antony Cruise. The pair also starred together in 1999’s Eyes Wide Shut, an erotic psychological drama that went on to become Stanley Kubrick’s final film before his death.
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Despite being the picture-perfect couple, the marriage of Cruise and Kidman did have its ugly sides. In 2015, a high up executive at the Church of Scientology claimed that he was instructed to “facilitate [Cruise’s] break-up with Nicole Kidman”, and it was revealed that Kidman’s phones had even been wiretapped on Cruise’s suggestion during the divorce.
Following their divorce, Nicole Kidman did an interview with Ladies’ Home Journal, during which she said: “He was huge; still is. To me, he was just Tom, but to everybody else, he is huge. But he was lovely to me and I loved him. I still love him.”
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However, Kidman did eventually move on, marrying Australian country singer Keith Urban in 2006. Urban and Kidman are still together to this day, and have two daughters together, with the youngest being born in 2010.
2. Sean Penn and Madonna
The relationship between the queen of pop Madonna and Fast Times at Ridgemont High star Sean Penn is another one that has been marred with controversy and speculation, even as it defined the gossip columns throughout the 80s.
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Penn met Madonna in February 1985, and the pair were married the following August, on Madonna’s 27th birthday. The following year, Madonna dedicated her third studio album True Blue to Penn, calling him “the coolest guy in the world”.
Sean Penn had previously been engaged to his Racing With the Moon co-star Elizabeth McGovern before meeting Madonna, and had even had a much talked about fling with Rocky Horror Picture Show star Susan Sarandon.
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For her part, Madonna had previously been in a serious relationship with John “Jellybean” Benitez, the DJ and producer who had produced her debut album in 1983. She started dating Penn after filming her iconic music video for Material Girl, which made headlines for paying homage to Marilyn Monroe’s Diamond’s Are a Girl’s Best Friend performance.
Madonna first filed for divorce in 1987, withdrawing the papers only to file them again two years later in 1987. In that time, she also filed an assault complaint, alleging that Penn had attacked her in her Malibu home. However, Madonna later dropped the charges, and said in a 2015 interview that they were: “completely outrageous, malicious, reckless, and false”.
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1987 was a difficult year for Sean Penn, as he was sentenced to 60 days in jail during that time, for assaulting a photographer on a film set. After his split from Madonna, Penn was in a string of high-profile relationships with the likes of Robin Wright and Charlize Theron, but he most recently married Australian actress Leila George in 2020.
1. Freddie Prinze Jr. and Sarah Michelle Gellar
From the state of all the gossip websites and celebrity magazines, it would seem as though there aren’t many happy endings to go around in Hollywood. However, that doesn’t mean that there aren’t any relationships that work out, as Freddie Prinze Jr. and Sarah Michelle Gellar have proven.
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This dreamy couple are so well matched that they have even been part of one of children’s television’s longest-running will they, won’t they’s. Prinze Jr. and Gellar played the gorgeous Fred and Daphne in both 2002’s Scooby-Doo and 2004’s Scooby-Doo: Monster’s Unleashed, with a chemistry that’s been unmatched in any other adaptation.
Sarah Michelle Gellar and Freddie Prinze Jr. met in 1997, when they were both starring in the teen horror flick I Know What You Did Last Summer. They immediately became fast friends, and remained as such for three years, until Prinze Jr. finally asked Gellar on a date in early 2000.
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The pair knew it was right immediately, and they tied the knot in a beachside ceremony in Mexico in 2002. They went on to have two children together, their daughter Charlotte was born in 2009, and their son Ricky was born in 2012. Most recently, the pair appeared together in Star Wars Rebels, lending their voices to various characters.
Despite being together for over a decade, the pair are still adorably enamoured with each other. Recently, Sarah Michelle Gellar even posted on Instagram saying: “Thank you Freddie for showing me what true love looks like. I loved you before children, but that love has intensified. Thank you for making my children the luckiest.”
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