These Iconic '90s Couples Will Have You Whispering, "Winona Forever"

Before dating Jennifers Lopez and Garner, Ben was linked to his Shakespeare in Love and Bounce costar Gwyneth Paltrow. They were together for three years before their split in 2000.

Gwyneth dated Brad Pitt, her costar in 1995's Seven. They got engaged but split in 1997 after three years together — but not before getting matching haircuts and cementing their place as one of the most attractive couples of the decade.

Matt and Minnie began dating in 1996 after starring together in Good Will Hunting — and because quippy celebrity couple names weren't a thing at the time, they missed an opportunity to be called "Mannie." Anyway, their relationship ended about a year later in a sort of cringeworthy way; Matt appeared on Oprah and denied having a girlfriend, so Minnie found out she was single along with the rest of the world.

Matt and Winona were introduced in late 1997 by none other than Gwyneth Paltrow, who at the time was good friends with Winona and also dating Matt's BFF, Ben Affleck. Winona and Matt hit it off and started a relationship, and she accompanied him to the Golden Globes in 2000, where he was nominated for his work in The Talented Mr. Ripley alongside Gwyneth Paltrow. They broke up later that year, but Winona had only good things to say about her ex in 2009. "Matt couldn't be a greater, nicer guy," she told Blackbook magazine. "I'm really lucky that I'm on good terms with him."

Johnny hooked up with his Edward Scissorhands costar Winona Ryder in the late '80s. Things got serious fast, and the two got engaged in 1990. Johnny got inked with his infamous "Winona Forever" tattoo, which he tweaked to read "Wino Forever" after they broke up in 1993. Winona has since called the split her "first heartbreak."

Ah, the supermodel and Hollywood heartthrob: a tale as old as time. Richard and Cindy began dating in 1987 (she was just 21 at the time) and were married in 1991. The difference in age was a pretty big deal at the time, but people were mostly just excited to see two overwhelmingly attractive celebrities fall in love with each other (another tale as old as time). They split in 1995, and Cindy has since blamed the failure of their marriage on the 17-year age gap: "I think I was more willing at 22 to be, like, 'Okay, I'll follow,'" she said in 2013. "But then you start going, 'Well, I don't want to just follow — I want to lead sometimes and I want to walk side by side sometimes.'"

SJP and RDJ famously began dating in 1984 after meeting on the set of Firstborn, and their breakup in 1991 was due in large part to Robert's drug problem. In an interview with Howard Stern in 2015, Robert revealed that he and Sarah Jessica had a friendly reunion in NYC and put their past issues to bed. "I said everything I wanted to say," Robert explained. "There's this familiarity that overtakes it and you realise you're just in the presence of this fully mature mother and woman and artist and human being. There's enough good will left over; you didn't burn that bridge." SJP echoed the actor's sentiment in October 2016: "It was surprisingly not weird. We were 18 when we met and fundamentally we are sort of the same. . . . It was completely familiar."

The Bush frontman and No Doubt frontwoman began dating in 1996 and tied the knot in 2002, bringing us plenty of rocker-cool moments in their 20 years together (not to mention their three adorable sons). They were the ultimate music couple in the '90s and 2000s, and their divorce in August 2015 definitely threw us for a loop.

After coming out in 1997, Ellen's first public same-sex relationship was with actress Anne Heche. They broke up after three and half years together, but their matching close-cropped blond 'dos and coordinating red carpet style will always be iconic.

Bruce and Demi got married in 1987 and divorced in 2000, and they share three daughters together: Rumer, Scout, and Tallulah. The two remained so close after their split that rumours persisted that they would remarry. Bruce famously attended Demi's 2005 wedding to Ashton Kutcher, and the blended family often hit the red carpet together with Bruce and his model wife, Emma Heming. These two might be the blueprint for staying friends after divorce.

We can't decide what was more memorable: Hugh Grant's relationship with Elizabeth Hurley, or Elizabeth Hurley's relationship with that Versace safety pin dress. The two began dating in 1987, and Liz gained instant media attention when she sported the supersexy gown at the premiere of Hugh's Four Weddings and a Funeral in 1994. Her name made headlines again a year later when Hugh was infamously arrested in LA for soliciting the services of prostitute Divine Brown. Liz stood by her man and made a public display of support at the Nine Months premiere a few weeks later. They split amicably in May 2000 after 13 years together and are friends to this day. After giving birth to her son Damian in 2002, Liz named Hugh as one of his eight godfathers, along with Elton John, Denis Leary, and the late Heath Ledger.

Kurt and Courtney were almost like prom king and queen when it came to the '90s alternative rock scene. Their relationship was plagued with controversy from the time they began dating in late 1991 and married a few months later: drug use (even while Courtney was pregnant with their only daughter, Frances Bean), volatile arguments, and of course, Kurt's suicide in 1994, which many still to this day blame Courtney for. The Hole frontwoman and Nirvana lead were only together for a few years, but their romance is still the stuff of grunge legend.

Somali supermodel Iman and English music legend David Bowie were introduced in 1990 and tied the knot in a private ceremony in Lausanne, Switzerland, two years later. The couple welcomed their daughter, Alexandria, in 2000, and shared David's son Duncan from a previous marriage. Sadly, David passed away in January 2015 after a battle with cancer, but Iman has stayed strong and exhibited grace and poise in the face of his tragic loss. Shortly after his death, Iman shared a poignant quote to social media: "The struggle is real, but so is God." She also paid tribute to her husband of 24 years with a touching photo on the one-year anniversary of his passing.

Melanie and Antonio began their relationship in 1995 after meeting on the set of the film Two Much (he was married at the time). Antonio and his first wife, Ana Leza, divorced in 1996, and one month later, he and Melanie tied the knot in London. Their daughter, Stella, was born in 1996. Antonio and Melanie announced their divorce in 2014. The following month, Melanie began the laser removal process for her famous "Antonio" tattoo.

Alec and Kim met on the set of The Marrying Man in 1990 and, coincidentally, got married three years later. They starred together in The Getaway in 1994. Their only child, daughter Ireland, was born in 1995. Kim and Alec announced their separation in 2000 and were divorced a couple of months later. In 2008, Alec wrote a book, A Promise to Ourselves: A Journey Through Fatherhood and Divorce, detailing his heated custody battle with Kim over their then 13-year-old daughter.

In 1997, Ryan attended a party in honour of Reese's 21st birthday. They reportedly spent all night talking to each other, and Reese made the first move. "I don't know what came over me — maybe the seven Midori sours — but I told him, 'I think you're my birthday present.'" OK, best line ever. They started dating, starred as an onscreen couple in Cruel Intentions, and tied the knot in 1999 while Reese was six months pregnant with the couple's daughter, Ava. Reese filed for divorce in 2006, but we'll always have the iconic romance between Annette Hargrove and Sebastian Valmont to look back on.

Model-actress Brooke Shields married tennis champ Andre Agassi in 1997 after four years together. They split in 1999, and Brooke opened up about their relationship in a revealing memoir in 2016; she alleged that Andre was "addicted to crystal meth" early in their romance and that he destroyed his tennis trophies after watching her film a flirtatious scene on Friends in 1996. She did, however, assert that despite his "affliction," Andre is "a really good human being."

River's younger brother Joaquin found love with Liv Tyler in 1995, when they were in their late teens. They starred together in 1997's Inventing the Abbotts and dated for three years. The two have managed to stay close friends; Liv has called Joaquin her "first love," and about Liv, Joaquin has said, "She's a darling. I've said it over and over again," and, "When Liv and I met, it was for a reason — I really needed her and she really needed me."

Will and Jada first met when she auditioned to play his love interest on The Fresh Prince of Bel-Air in 1994. She didn't get the role (it went to Nia Long), but the two became friends and soon started dating. They were married in 1997 and began a beautiful tradition of dominating the red carpet together. They have two kids, Jaden and Willow, as well as Will's son Trey from his first marriage. The best part about Will and Jada's love story? They're still together!

While filming Best Men and Home Fries together in 1997, Drew fell in love with Luke Wilson. They split two years later, but damn, they were so cute together.

Remember these two?! Cameron and Matt started dating in 1995 and starred together in There's Something About Mary three years later. They broke up shortly after filming wrapped.

This one was a doozy. Whoopi and Ted became friends after meeting as guests on The Arsenio Hall Show in 1988, but it wasn't until they starred together in Made in America in 1992 that a romance blossomed. The one tiny issue was that Ted was married at the time (to his second wife, Cassandra "Casey" Coates), and his affair with Whoopi led to their $30 million divorce. Their relationship survived a racially charged stand-up routine, but they ultimately called it quits in 1993.

Jude Law married the actress, producer, and fashion designer in 1997 after meeting three years earlier. They have three children together and divorced in 2003. Shortly after the split, Jude began his tumultuous relationship with Sienna Miller.

Alyssa and Scott had a very public relationship in the '90s; they met on the set of the film Double Dragon in June 1993 and moved in together two months later. The Party of Five star popped the question two months after that, and in a joint interview with People in 1994, Scott said, "I'm convinced we're like two halves of the same soul." While he told the interviewer, "You can interview us 25 years from now," Scott and Alyssa ended their relationship shortly after. Oops.

Susan and Tim met while filming Bull Durham in the late '80s and became one of Hollywood's most enduring couples over the next two decades. They never got married but shared two sons together, as well as Susan's daughter Eva from her previous relationship with Italian filmmaker Franco Amurri. When they announced the end of their partnership in 2009, our hearts collectively broke.

The lasting memory from Marilyn Manson and Rose McGowan's three-year relationship will always be the nondress she wore when the couple attended the 1998 MTV VMAs together. The rocker and Charmed actress broke off their engagement in 2001, and over a decade later Rose blamed their split on cocaine.

Yup, before Brad Pitt and Justin Theroux, Jennifer Aniston was engaged to actor Tate Donovan. They began dating in 1995, long before he played her love interest, Joshua, on Friends. They got engaged in 1997, but the romance ended in 1998.

Related:

Everyone Jennifer Aniston Has Dated, From Brad Pitt to Justin Theroux

Jennifer's Friends costar Courteney Cox also had a high-profile relationship. She and Michael Keaton met in 1989 and dated for six years before they called things off in 1995. They were intensely private about their romance, but shortly after their split, Courteney 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."

Busy Philipps and Colin Hanks dated in 1997 while they were both students at Loyola Marymount University and both trying to make it in Hollywood. The couple recently reunited on Live! With Kelly and talked up their close friendship.

Claire Danes and Aussie singer Ben Lee were introduced in 1997 by none other than Winona Ryder. They dated until 2003, and their split was reportedly due to Claire's affair with her Stage Beauty costar Billy Crudup, who was then married to a very pregnant Mary-Louise Parker.

In a move nobody saw coming, Julia Roberts married country singer Lyle Lovett in June 1993, just three weeks after they met. They separated and divorced in March 1995.

Halle Berry first saw Atlanta Braves all-star David Justice playing in an MTV Rock n' Jock softball game (how '90s is that?!) in 1992. A reporter later told her that David was a fan, so she gave her number to the reporter to pass on to him. They began dating and tied the knot at midnight on Jan. 1, 1993.

Unfortunately, their cuteness didn't last long; when Halle filed for a restraining order after their divorce in 1997, many accused David of domestic violence — the Oscar winner has spoken publicly over the years about an ex-boyfriend that "caused permanent hearing loss to her left ear," but has never named names. David has railed against the reports over the years, saying, "David Justice is not the person who hit her on her head and caused her hearing loss. Not only did David Justice not do that, David Justice never hit her, period."

America's sweetheart Meg Ryan fell in love with Dennis Quaid when they starred together in 1989's D.O.A. They got married on Valentine's Day in 1991 and welcomed their son, Jack, the following year. The couple separated in 2001, and Meg later revealed, "Dennis was not faithful to me for a long time, and that was very painful."

Sofia Coppola and Spike Jonze met in 1992 and likely bonded over making dreamy, complicated films with amazing soundtracks. They got married in 1999 but split in 2003. Sofia's critically acclaimed Lost in Translation was released that same year — Spike is thought to have inspired Giovanni Ribisi's character, while his 2013 Academy Award-winning Her is rumoured to be a response.

Another match made in indie movie heaven, Chloë Sevigny and Harmony Korine met in NYC's Washington Square Park in 1993, when she was a senior in high school. He was so taken by the Connecticut native that he cast her in his iconic cult film Kids two years later. Their friendship blossomed into a romance, and they dated until 1997.

Heather married the Bon Jovi guitarist in 1994, just a year after divorcing Motley Crüe drummer Tommy Lee. They had a daughter, Ava, together, and seemed to be one of the rock star-actress couples that would actually make it. Sadly, they divorced in 2006.

The year was 1998: Jennifer Love Hewitt was the teen movie queen, starring in I Know What You Did Last Summer and Can't Hardly Wait, and Carson Daly was spending his afternoons being screamed at by overexcited teenagers on the set of TRL. The two got together, but the relationship crashed and burned a year later (but not before Carson got a tattoo of her name on his leg). Carson apparently found out that Jennifer had dumped him via Howard Stern's radio show — ouch. The two awkwardly settled their beef on air when Jennifer appeared on his talk show Last Call With Carson Daly in 2005, and he even congratulated her on her engagement to now-husband Brian Hallisay in 2013.

Michael Jackson and Lisa Marie Presley first met when she was seven years old — her dad, Elvis Presley, took her along to The Jackson Five's Las Vegas concerts. They met again as adults in 1992 and bonded over their shared childhood experiences (or lack thereof) and things soon turned romantic. Lisa Marie stayed by Michael's side during his 1993 child sexual abuse accusations and as he embarked on his Dangerous World Tour, Michael proposed at Neverland Ranch. Lisa — who was married to and shared two children with actor Danny Keough at the time — divorced her husband just 20 days before she and Michael tied the knot in a last-minute ceremony while vacationing in the Dominican Republic in 1994.

News outlets had a field day with the union, and that August, Lisa issued a statement confirming the news: "My married name is Mrs. Lisa Marie Presley-Jackson," she said. "I am very much in love with Michael, I dedicate my life to being his wife." A few weeks later, they proved that point by making out on stage at the MTV VMAs, and literally nothing was the same. Their divorce was finalized nearly two years to the day after that public kiss, though Lisa Marie told Oprah in 2010 that they spent the next four years after their split "getting back together and breaking up." It's been two decades — and Michael is now gone — but this relationship still has us shook.

To say that Fiona Apple was attracted to the quirky type is probably an understatement. She and six-time Oscar nominee Paul Thomas Anderson have been lovingly called the "coolest, dorkiest, sexiest, and most indelible celebrity power couple of the '90s," a statement we will gladly cosign. Not only did they begin dating in 1997, but Paul and Fiona also 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," and after their 2000 breakup, the two reunited to work on the video for "Hot Knife" over a decade later. Paul is now married to SNL alum Maya Rudolph, but he and Fiona have remained civil — "Paper Bag" was even featured in Maya's hit comedy Bridesmaids in 2011.

Opposites attracted in 1991 when Emilio and Paula began dating. They got married in 1992 but divorced two years later.

David cast his spell on the German supermodel in 1993 at a Berlin gala — literally. He brought her on stage to participate in a mind reading act and a flying illusion, and they got engaged a year later. She made multiple appearances during his magic shows, acting as his "special guest assistant" in illusion acts. They ended things in 1999.