Top 10 Iconic Celebrity Couples of the 1990s
#10: Tim McGraw & Faith Hill
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These two first met in Nashville in 1994 when they were both fresh faces on the country music scene. They met at a country music radio seminar and while they got along, Hill was recently divorced and McGraw was in a relationship. Cut to a couple of years later in 1996 when Hill opened for McGraw on his Spontaneous Combustion tour. Now McGraw is single but Hill is engaged. This time the chemistry between the two future country music superstars was undeniable and Faith broke off her engagement. The couple married in October of 1996 and in 1997 they had their first child and their first chart-topping single together, “It’s Your Love.” And they would go on to have more of each.
#9: Hugh Grant & Elizabeth Hurley
These two lovebirds met in 1987 and dated all through the 90s. Hurley was one of the most beautiful women in the world and as many of us remember, Grant became a rom-com king after his breakout role in “Four Weddings and a Funeral” in 1994. However, many of us also remember the 1995 scandal when Hugh was arrested with a sex worker. This very easily could have been the scandal to end his career and his relationship. However, his apology tour, which included a now-famous appearance on “The Tonight Show with Jay Leno” worked on the fans, and his apologies at home must have worked on Hurley. The couple remained together until 2000 and even 20 years later are the best of friends.
#8: Will Smith & Jada Pinkett Smith
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Will first met Jada when she came in to audition to play his girlfriend on “The Fresh Prince of Bel-Air.” She didn’t get the role on the show, but she would get the role in real life a few years later. The couple married in 1997 and have been very open about the ups and downs of their relationship, even going so far as to sit down and talk it out in front of the camera in 2020. But, while it might not all be smooth like the summer, summer, summertime, these two found the groove that soothes and moves romance back in the 90s and kept it going for over 20 years.
#7: David & Victoria Beckham
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While most couples on this list didn’t see their 90s relationships continue into the 2000s, even fewer made it to 2020 and beyond with the same partner. One of the couples that did is none other than David and Victoria Beckham. And it all started in 1997 in the Manchester United players’ lounge. It’s where the uber-famous Spice Girl and the soccerball-bending superstar first laid eyes on each other. And, at least for Posh Spice, it was love at first sight. As she told British Vogue, “Love at first sight does exist. It will happen to you in the Manchester United players' lounge — although you will get a little drunk, so exact details are hazy.” Looks like she got what she really, really, wanted.
#6: Brad Pitt & Gwyneth Paltrow
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Brad and Gwyneth played a couple in the 1995 film “Seven,” and behind the scenes, they became a couple IRL as well. In fact, when Pitt won the Golden Globe for his performance in the film “12 Monkeys” he called Paltrow his “angel, the love of [his] life” and by the end of 1996, they were engaged. But by June 1997, they were done and not too long after that, Paltrow would meet her next paramour on the set of “Shakespeare in Love.” Of course, we’re talking about Ben Affleck, whom she dated on and off until 2000.
#5: Cindy Crawford & Richard Gere
What happens when one of Hollywood’s biggest stars and one of the world’s most beautiful fashion models get together? You get one of the 90s’ most iconic couples of course! And that’s truly what Crawford and Gere were. From their first meeting in 1988, to their spur-of-the-moment Vegas wedding in 1991, to their divorce four years later. And while they were both famous when they met, their celebrity status just kept rising during their time together. Gere’s role in “Pretty Woman” had people everywhere climbing fire escapes to declare their love and Crawford made Pepsi the sexiest soda around. In the end, though, the 17-year-age difference was too much to overcome and both parties moved on separately.
#4: Kurt Cobain & Courtney Love
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Cobain and Love’s relationship was as iconic back in the early 90s, when it happened, as it remains to this day. Love was one of the biggest female stars on the alternative music scene and after the release of “Nevermind” in 1991 Cobain would forever be a grunge god. There are varying accounts of how, and when they first met and the story surrounding Cobain’s death has been drenched in controversy and conspiracy for decades. But for a brief few years in the first part of the last decade of the 20th century, this relationship was alternative royalty.
#3: Michael Jackson & Lisa Marie Presley
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Yes, in case you have been living under a rock for a few decades, it’s true. Michael Jackson and Lisa Marie Presley dated and were married in the 90s. The two were just friends when the 90s began, but when Jackson was neck-deep in controversy in 1993, Lisa was who he looked to for support. That same year he proposed to her over the phone and they were married in January of ‘94. But by the end of the following year, divorce papers had been filed. It seems quick, but it’s longer than many thought it would last, including the judge that married them, who said, “I gave them a year. They lasted a year and a half.”
#2: Nicole Kidman & Tom Cruise
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Prior to meeting Tom Cruise, Kidman had been in three serious relationships but had decided that she was never going to get married. Then, a 21-year-old Kidman met Cruise while making “Days of Thunder” together and her plans changed. The pair were married in 1990 and spent the entire decade together, including over a year making Stanley Kubrick’s last film, “Eyes Wide Shut.” While the marriage made it through the 90s, the 2000s wasn’t meant to be and by February of 2001, divorce papers were being filed. And for everyone who saw Kidman’s “infidelity” speech in “Eyes Wide Shut” as a reflection of the state of the couple's marriage at the time, she says, “I definitely didn't see it like that.” Before we unveil our top pick, here are a few honorable mentions. Jennifer Lopez & Sean Combs They Started Dating in 1999 & Announced Their Breakup on Valentine’s Day 2001 Claudia Schiffer & David Copperfield Nope, It Wasn’t an Illusion: Schiffer & Copperfield Were Engaged from 1994-99 Whitney Houston & Bobby Brown It Wasn’t Without Controversy, but They Were Married from 1992 Until 2007 Reese Witherspoon & Ryan Phillippe The “Cruel Intentions” Co-stars Were Married in 1999 & Separated in 2006 Kate Moss & Johnny Depp The Iconic Model & the Acting Icon Dated from ‘94 to ‘98
#1: Justin Timberlake & Britney Spears
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While these two former Mouseketeers confirmed they were dating in 1999, reports have them together starting in 1998. Either way, they meet the criteria for this list and in so doing find themselves right at the top of it. These two were on top of many people’s lists back then, but although couples that dress in denim together usually stay together, for Justin and Britney, it wasn’t meant to be and they broke up in 2002. And for the one or two people who forgot these two dated back then, they were reminded of it years later with the release of the 2021 Spears documentary and the controversy surrounding how JT treated her post-break-up.
