The Nineties It-couples that defined a generation

The Nineties was an era defined by many things: raving, Body Shop’s White Musk, Britpop, Keanu Reeves’ leather chaps and, perhaps most memorably, the Macerena. But while the rest of us were thrusting exuberantly to the dulcet tones of “Mac, mac, mac, mac, mac, mac, Macarena”, the ‘90s It-couples were smouldering around Primrose Hill or downtown LA dragging on a cigarette and generally looking bored and incredibly attractive.

In a serious blast from the past this week, supermodel and ‘90s icon Kate Moss took the stand (via video link) at ex-boyfriend Johnny Depp’s defamation trial in which he’s suing Amber Heard for $50 million. The couple are said to have had little contact since their breakup 25 years ago, but their four-year relationship is still one of the most iconic pop-culture couplings since John Lennon and Yoko Ono, just with slightly less hair and slightly more cocaine.

Images of the pair attending film premieres or stumbling out of hotels dressed in biker jackets, distressed denim and a louche cigarette dangling oh-so nonchalantly from pillowly lips have almost singlehandedly kept Tumblr in business and cemented their place in the cultural zeitgeist. In homage to the lovers that came to define a generation, we have put together a who’s who of the most glamorous ‘90s couples for you to drool over.

Kate Moss and Johnny Depp

Undoubtedly the king and queen of all the ‘90s couples, the genetically blessed pair got together after being introduced at Cafe Tabac in New York’s East Village in February 1994 by a mutual friend. Rumour has it, then 20 year-old Kate Moss, and 31 year-old Depp talked all night before retreating to the actor’s hotel room where they remained for several days. About their initial meeting, famously coy Moss recalled: “I knew from that moment that we would be together . . . We just sat down and talked sheer nonsense, and from that moment didn’t want to be apart.”

After fours years and a lifetime’s worth of frame-worthy paparazzi shots, the couple broke up much to the nation’s collective despair. As Depp’s career catapulted to new heights after the release of the Tim Burton classic Edward Scissorhands, he was often away filming back-to-back projects, which left Moss feeling lonely and melancholy. The model said: “I was going insane. I’m not normally a depressed person, but I got really sad . . . and we grew apart.” Depp eventually broke things off in 1998 following the Cannes Film Festival, where Moss was banned for life from the Hotel Du Cap hotel for allegedly running up and down the corridors in a bikini and trashing her hotel room. A few weeks after their breakup Depp walked past Vanessa Paradis in a hotel lobby in Paris and three months later she was pregnant with their first child. Meanwhile Kate checked into The Priory for a five-week stint and in an interview with Vanity Fair said she “cried for years” about the breakup. Sigh.

Sadie Frost and Jude Law

Fellow alumni of the notorious Primrose Hill set, which included Moss, Depp and the Gallagher brothers, were actors Sadie Frost and Jude Law. After hitting it off on the 1992 film Shopping, Frost, then 25, left her nine year marriage to Spandau Ballet’s Gary Kemp to be with her 19-year-old co-star. Writing in her autobiography Crazy Days, Frost wrote: “The force of the love I felt for Jude and his intense ambition made me feel out of control.” But after being diagnosed with postnatal depression after the birth of their son Rafferty and Jude’s frequent absences due to his busy filming schedule things began to unravel. Recalling her pregnancy, Frost wrote: “Jude was away a lot, while I was sitting on the sofa, getting fatter and gripped by a nagging sense that I was jeopardising my love.” After eleven years together the couple broke up on a holiday in Thailand after Frost asked Law if he loved her anymore and he replied that he didn’t. After their return to the UK, Law moved out of the family home and Frost filed for divorce in August 2003. The actress said it took her six years to get over Law’s decision to end the relationship.

Carolyn Bessette and JFK Junior

One of the more tragic ‘90s golden couples. John Kennedy Jr, the son of assassinated John F. Kennedy and former First Lady Jackie Kennedy, met Bessette in1992 while she was working as a publicist for Calvin Klein and he was dating actress Daryl Hannah. The couple got together in 1994 and became engaged a year later. The New York socialites wed in a secret ceremony on a tiny island called Cumberland, off the coast of Georgia in September 1996, with only their closest friends and family in attendance. Carolyn wore a silk slip dress made by former Calvin Klein designer Narciso Rodriguez, which remains one of the most googled wedding dress inspo pictures of all time.

Despite their low-key romance and aversion to the limelight the couple came to define the ‘90s aesthetic, largely thanks to Carolyn’s Upper East side take on simple, grunge 90s style. After three years’ of marriage the couple’s union began to hit the rocks and they sought couple’s therapy after Bessette reportedly began feeling trapped in the oppressive Kennedy bubble. Around the same time JFK Jr. acquired his pilot’s license and decided to fly his wife and her sister Lauren to the wedding of his cousin Rory Kennedy despite being advised not to due to limited visibility. Tragically the plane crashed, killing all three passengers in the summer of 1999.

Liv Tyler and Joaquin Phoenix

These Hollywood heavyweights met while filming the romantic drama Inventing the Abbotts. “I fell in love with Joaquin the second I saw him,” Tyler told The Morning Call in 1997. After getting together while filming, the couple attempted to keep their relationship a secret from the crew, but inevitably the truth came out and the pair embarked on one of the sweetest relationships in ‘90s Hollywood history. At the time, Tyler said: “I didn’t feel threatened or afraid of the idea to get involved with him when we were working… I just kind of knew and hoped and prayed that I would love him forever.” The pair eventually went their separate ways because, according to Phoenix, the couple stopped arguing, speaking to Cosmopolitan in 1999. “When you become satisfied, you stop fighting, and I like fighting. It means that I’m constantly progressing and evolving. I’m never satisfied, and hopefully, I never will be.” The pair are still great friends and Tyler has referred to his sisters as like her own family.

Gwyneth Paltrow and Brad Pitt

The blonde bombshells met in 1995 on the set of gory thriller Se7en, and very shortly became the most beautiful couple to walk the earth. But unlike their doomed on-screen counterparts, where Paltrow’s head is presented to Pitt in a box, their IRL relationship went from strength to strength, and became the stuff of tabloid editors’ wet dreams.

After a year of dating both their careers seemed on the rapid ascent with Paltrow playing Emma in the Oscar-winning 1996 remake and Pitt eschewing his pretty-boy image for gritty parts that led him to win a Golden Globe for his role in 12 Monkeys. Breaking every girl’s heart in the process, Pitt dedicated his award to Paltrow, calling her “the love of my life, my angel, Gwyneth Paltrow”. Soon after, Pitt asked Paltrow’s beloved father Bruce for her hand in marriage and the pair began to morph into the same person, dressing in matching black suits and getting the same choppy haircut and lemon-blonde highlights. It seemed preposterous then, just six months after the engagement, that the couple called it quits. Speaking in 2015 to Howard Stern about the split, Paltrow said: “ You can’t make that decision when you’re 22 years old … I wasn’t ready, and he was too good for me … I didn’t know what I was doing.”

Minnie Driver and Matt Damon

These two young stars met on the set of Damon’s Oscar-winning classic Good Will Hunting in 1996. Driver almost missed out on the role that launched both her and Damon’s career after Harvey Weinstein allegedly told the casting director “nobody would want to fuck her”. Ignoring Weinstein’s remarks Damon cast Driver as his love interest, Skylar, and the couple soon began dating in real life.

While promoting the film on the Late Show With David Letterman, Damon gushed about his relationship, stating that she “pretty much rocked my world.” But things took a turn for the worst, when appearing on the Oprah Winfrey show a month later Damon told the host he was single, much to Driver’s surprise.

Speaking to the Los Angeles Times six months after her very public dumping, Driver said: “It’s unfortunate that Matt went on [the show]. It seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically inappropriate.” The actress recalled how the following year’s awards circuit, in which Damon and Ben Affleck won Oscars for Good Will Hunting, was extraordinarily awkward. In fact, a cameraman at the Academy Awards was tasked with following Driver around in case she made a scene.