17 of the most iconic '90s celebrity marriages we're still obsessed with

Pamela Anderson and Tommy Lee at a 1995 Grammys awards after-party.
Pamela Anderson and Tommy Lee in 1995.Jeff Kravitz/Getty Images
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  • Supermodel Cindy Crawford was married to actor Richard Gere for a few years back in the '90s.

  • For a time, "Pretty Woman" leading lady Julia Roberts was married to country singer Lyle Lovett.

  • Tommy Lee and Pamela Anderson got married in 1995 after knowing each other for just a few days.

"Dangerous Liaisons" star Uma Thurman kicked off the '90s by marrying actor Gary Oldman in 1990.

Gary Oldman and Uma Thurman
Gary Oldman and Uma Thurman.Ron Galella/Getty Images

At just 18 years old, Thurman met a 30-year-old Oldman in 1989 while they were filming the movie "State of Grace."

They only dated briefly. In 1990, Oldman married Thurman, just one year after he divorced his then-wife Lesley Manville.

Ending their relationship just as quickly as it started, Thurman and Oldman divorced in 1992.

"We met when I was 18," Thurman told Vanity Fair in 1996. "He was 12 years older. It was a crazy love affair that ended, as it needed to. He was my first love. I had no prior experience." She added that the marriage was a "mistake," but called Oldman a "truly great actor."

Award-winning actors Tom Cruise and Nicole Kidman were one of Hollywood's "It Couples" in the '90s. Within a year of meeting, Kidman and Cruise said their "I dos" in 1990.

Tom Cruise and Nicole Kidman
Nicole Kidman and Tom Cruise.Steve Granitz/Getty Images

Meeting on the set of "Days of Thunder" in 1990, Kidman and Cruise described their romance as a beautiful love story when they were married.

Cruise told Vanity Fair in 1994 that meeting Kidman "was that special connection when you recognize your soul mate."

"He basically swept me off my feet," Kidman later told Vanity Fair in 2002.

The couple adopted two children together, Isabella and Connor, in 1992 and 1995, respectively.

But their fairytale-seeming relationship ended in 2001 with divorce, as documented by the iconic photos of Kidman reportedly celebrating the news.

Another '90s A-list wedding was between "Pretty Woman" star Richard Gere and supermodel Cindy Crawford in 1991.

Cindy Crawford and Richard Gere
Cindy Crawford and Richard Gere.Ron Galella, Ltd/Getty Images

The two met at the late photographer Herb Ritts'  barbecue in the late '80s, and started dating soon after. Crawford and Gere made it to the altar in 1991, in part, because of an ultimatum Crawford gave Gere (according to him).

"I was a holdout at age 42," Gere told The Mirror. "This woman who I was crazy about and loved very much said, 'I can't wait. I gotta move on if it ain't happening.'"

After four years of marriage they called it quits in 1995. Crawford later cited their age gap as the catalyst for their divorce during an episode of "Oprah's Master Class." "Richard's a super smart guy, and he's interesting, and he's interested, and I learned a lot about the world," she added. "It was a great chapter in my life."

Multi-hyphenate Paula Abdul took "The Breakfast Club" star Emilio Estevez's hand in marriage in 1992.

Paula Abdul and Emilio Estevez
Paula Abdul and Emilio Estevez.Ron Galella/Getty Images

According to People, their first in-person date date happened in 1991 at the Plaza Hotel. The "Mighty Ducks" star called Abdul from the hotel and asked her to dinner, as they both happened to be staying there at the same time. Up until that point, their relationship was just phone conversations.

Six months after their first date, Estevez popped the question to Abdul, and they tied the knot in a Santa Monica courtroom in 1992.

But in 1994, their love story ended in divorce after Abdul wanted kids and Estevez, already a parent of two, did not. "It was very hard for him to admit that he couldn't handle having kids again," Abdul told People. "It was heartbreaking for us both."

Supermodel Iman and rock star David Bowie, arguably the most photogenic couple of the 1990s, got married in 1992, which was a major highlight of the decade.

David Bowie and Iman
David Bowie and Iman.Ron Davis/Getty Images

Bowie set out to date Iman after seeing her in a magazine while he was touring in 1990, as reported by People.

With the help of hairstylist Teddy Antolin (a mutual friend of Bowie and Iman), he was able to meet her at Antolin's birthday party in October 1990, and from that point on, they were "inseparable."

For the next two years Iman and Bowie dated until getting hitched in 1992 in Italy, combining their two empires (and families) together.

In addition to both Bowie and Iman having a child from prior relationships, they also had a daughter together, Alexandria.

Even decades after their glamorous wedding day, their love never seemed to wane. Iman remained married to Bowie until he died in 2016 at 69 years old.

Grunge rock pioneers Kurt Cobain and Courtney Love were both artistically and romantically compatible. They got married in 1992.

Courtney Love and Kurt Cobain
Courtney Love and Kurt Cobain with their daughter Frances Bean Cobain.Jeff Kravitz/Getty Images

It's unclear when exactly Love and Cobain met, but according to Far Out Magazine, it was sometime in the late '80s or early '90s.

Although he always "liked" her, Cobain's desire to remain a bachelor at the time prompted him to not get involved with Love.

"I was determined to be a bachelor for a few months … but I knew I liked Courtney so much right away that it was a really hard struggle to stay away from her for so many months," Cobain was quoted saying in the short film "Come As You Are."

Eventually, Cobain made things official with Love in 1991, and in 1992 they tied the knot on Waikiki Beach in Hawaii after finding out Love was pregnant.

While they did face turbulent times in their marriage, including multiple overdoses and investigations by Child Protective Services, Love remained married to Cobain until his self-inflicted death in 1994, and are still regarded as one of the most important rock-and-roll couples of all time.

Bobby Brown and Whitney Houston's relationship made many headlines once they jumped the broom in 1992.

Whitney Houston and Bobby Brown
Whitney Houston and Bobby Brown.Ron Galella, Ltd/Getty Images

The public's interest in Houston and Brown as a couple (which intensified over time), resulted in many tabloid think-pieces and comedy spoofs, like the one comedians Debra Wilson and Aries Spears did on the sketch comedy series "Mad TV" in the 2000s.

Despite the opinions surrounding their entire marriage, what can't be negated is the beauty that radiated on their wedding day.

Both Houston and Brown wore all-white, and exchanged vows at Houston's estate in New Jersey.

Aside from the spectacle that their union turned into, their special day has gone down as one of the most iconic weddings of the '90s.

Brown and Houston divorced in 2006. Houston died in 2012. Their daughter, Bobbi Kristina Brown, died in 2015.

In his 2022 documentary "Biography: Bobby Brown," Brown said that he thought "we could have helped each other out," and he thought "she'd still be here if we hadn't divorced," People reported.

Mariah Carey marrying Tommy Mottola in 1993 was a definitive moment in music history. At the time, she was a 24-year-old budding R&B superstar and Mottola was the 44-year-old CEO of Sony Music.

Mariah carey and tommy mottola
Mariah Carey and Tommy Mottola.Ron Galella/Getty Images

Despite their 20-year age gap, the relationship became an iconic part of pop culture because of how prominent they both were in the music industry. In fact, Mottola is partly responsible for Carey's early success as an artist.

Mottola discovered a 19-year-old Carey in 1988, and signed her to Columbia records (a subsidiary of Sony Music) in 1990. It was the catalyst for Carey's game-changing career, and one of the most important moments in pop culture history.

Converting their beneficial business relationship into a marriage in 1993 provided even more publicity, and (intended or not) pushed Carey further to super-stardom.

Of course, their actual wedding is mostly remembered for Carey's legendary Vera Wang dress, a giant bouffant-style gown with puffy sleeves.

Their marriage ended in 1998. Years later, in 2019, Carey told Cosmopolitan that being in her first marriage "was almost like being a prisoner," and that there was "no freedom for me as a human being."

Julia Roberts and Grammy-winning country singer Lyle Lovett made their relationship official by tying the knot in 1993, after dating for less than a month.

julia roberts lyle lovett
Lyle Lovett and Julia Roberts.Jim Smeal/Ron Galella Collection/Getty Images

Roberts and Lovett seemed almost fated to be together — they had mutual friends, they worked together on Robert Altman's 1992 film "The Player," and Roberts was a big fan of Lovett's music.

Apparently, it didn't take long for these Hollywood powerhouses to realize their compatibility. In June 1993, Roberts and Lovett tied the knot at St. James Lutheran Church in Marion, Indiana. They had only known each other for a few weeks.

Their traditional ceremony was so major that People called it "the biggest thing to happen in Marion, Indiana, since the high school basketball team won back-to-back state championships in the mid-'70s" in their July 1993 cover story.

"We've never gone more than a week without seeing each other since we got married," Lovett told People in December 1993. "But before that we'd never spent more than seven days together."

They called it quits in 1995.

Mötley Crüe drummer Tommy Lee and "Baywatch" star Pamela Anderson skipped the dating phase altogether by getting married just a few days after meeting in Mexico.

Pamela Anderson and Tommie Lee
Pamela Anderson and Tommy Lee.Steve.Granitz/Getty Images

Since Lee and Anderson got married after knowing each other for less than four days, their ceremony was rather spur-of-the-moment. That's at least part of the reason they got married on the beach in Mexico in their swimwear.

Their love affair was a whirlwind, but it came to a screeching halt when they divorced in 1998. Between the strain of their sex tape getting broadcast across the internet, drug abuse, allegations of physical abuse, and career struggles, their marriage couldn't take it.

Of course, Lee and Anderson tried to make it work multiple times after their divorce, but at this point, they seem to be truly done.

Insider reported that Lee and Anderson tried to give their love another chance in 2008, but called it quits in 2010.

Despite their actual marriage being short-lived, Lee and Anderson have gone down as one of the most infamous celebrity couples ever. Lee and Anderson share two children together, Brandon and Dylan.

Sean Penn and Robin Wright had two kids before they got married in 1996.

sean penn robin wright
Robin Wright and Sean Penn.Robin Platzer/Images/Getty Images

Penn and Wright fell in love quickly after meeting on the set of the 1990 film "State of Grace" (which happens to be the same film where Uma Thurman met Gary Oldman).

Both had recently gotten divorced around the time they got together (Penn divorced Madonna in 1989, while Wright got divorced from "Santa Barbara" co-star Dane Witherspoon in 1988).

It took them six years and two kids to tie the knot, though. Their daughter Dylan was born in 1991 and their son Hopper was born in 1993. They didn't get married until 1996.

Penn and Wright divorced in 2010.

"'When you get divorced, all the truths that come out, you sit there and you go, 'What the f--- was I doing? What was I doing believing that this person was invested in this way?' Which is a fantastically strong humiliation in the best sense," Penn told Esquire in 2012.

Country music stars Faith Hill and Tim McGraw haven't missed a beat since they got married in 1996, remaining inseparable for the last 26 years.

Tim McGraw and Faith Hill
Tim McGraw and Faith Hill.Ron Gallela/Getty Images

It was "love at first sight" for McGraw when he met Hill at the Country Radio Seminar showcase for new artists in 1994, but not for Hill, since she had just divorced her husband, music executive Daniel Hill.

Eventually, Hill's feelings developed for McGraw, and in 1996, while on the "Combustion" tour with a newly single McGraw, Hill broke off her engagement with record producer Scott Hendricks to pursue a relationship with the fellow country music sensation.

"If someone is going to judge my character because I was engaged to somebody and then I left him for somebody else," Hill told People in 1998, "I can't control that. But I wasn't about to let Tim slip through my hands."

A few months into touring McGraw proposed to Hill, and the two got married in a private wedding ceremony in Rayville, Louisiana (McGraw's hometown).

They have three daughters, and still regularly work together.

"Sex and The City" icon Sarah Jessica Parker and "Ferris Bueller's Day Off" star Matthew Broderick haven't wavered from one another since they exchanged vows in 1997.

sarah jessica parker matthew broderick
Matthew Broderick and Sarah Jessica Parker.Darlene Hammond/Getty Images

Going through a public breakup, like Parker did with Robert Downey Jr. in 1991, can be difficult, but sometimes family can help ease the pain, just like Parker's brother did when he introduced her to Broderick later that year.

It took a few months for Broderick to ask her out, though."He left a very charming, very self-effacing message on the machine," Parker told The New York Times in 1996. "You know, 'Hi, it's Matthew Broderick.' You had to use your last name."

Six years after meeting, the two got married in a surprise ceremony with 100 guests, who they invited to a synagogue in Manhattan's Lower East Side, under the guise of a regular party.

In true Carrie Bradshaw fashion, Parker daringly wore a black gown for her nuptials instead of a traditional white wedding dress.

They have three kids together, and recently wrapped up a successful run co-starring in the Broadway play "Plaza Suite."

Will Smith and Jada Pinkett Smith said "I do" in 1997, and are still together to this day through ups and downs.

Will Smith and Jada Pinkett-Smith
Will Smith and Jada Pinkett Smith.Steve Granitz/Getty Images

The Smiths' romance starred off a bit controversially, as Smith realized Pinkett was "the one" while still married to his ex-wife Sheree Zampino.

"I had a realization I wasn't with the person I was supposed to be with," Smith said during a 2018 episode of "Red Table Talk." "I was sitting in a stall and I was crying and laughing uncontrollably, and I knew [Pinkett] was the woman I was supposed to be with, but I was never getting divorced."

However, the two did get divorced, and Smith and Pinkett quickly began dating. They were married on New Year's Eve in 1997 at a hotel in Baltimore, Pinkett's hometown.

After 25 years of marriage and two kids (Jaden and Willow), the Smiths are still holding onto their love, despite having some hurdles to overcome in their relationship.

For example, Pinkett Smith's "entanglement" with R&B singer August Alsina back in 2016 (that came to light in 2020), the reveal that she initially didn't want to marry Smith during a 2018 "Red Table Talk" episode, or, of course, "The Slap."

Uma Thurman and Ethan Hawke fell in love instantly after meeting on the set of the 1997 sci-fi thriller film "Gattaca." They were married the next year.

uma thurman ethan hawke
Ethan Hawke and Uma Thurman.Richard Corkery/NY Daily News Archive/Getty Images

Despite them being a handsome couple, their marriage ended in 2003, after they welcomed two children together, including "Stranger Things" star Maya Hawke.

Two years later, Thurman simply said, "Our marriage failed. I should take full responsibility for the failure of my own marriage," during a 2005 interview with Oprah Winfrey.

For his part, Hawke has expressed that he simply wasn't ready for such a big commitment. "There was this discovery that the male brain isn't done until 28. I definitely think my frontal lobe was not finished. I had no business taking vows that would last more than two weeks," Hawke told Elle in 2013.

That same year, Hawke also said that "'Gattaca' was a great moment in my life and a great moment in Uma Thurman's life, and we fell madly in love and wanted to do all that," according to Us Weekly.

Ryan Phillippe and Reese Witherspoon, co-stars of the iconic '90s film "Cruel Intentions," made their way to the altar in 1999.

Reese Witherspoon and Ryan Phillippe
Reese Witherspoon and Ryan Phillippe.Steve Granitz/Getty Images

In 1997, Phillippe met Witherspoon at her 21st birthday party, way before they co-starred in the 1999 movie "Cruel Intentions" together, even though many thought the two met on set.

During an episode of "Watch What Happens Live With Andy Cohen" in 2015, Witherspoon explained that she and Phillippe were "living together for about a year and a half" before filming "Cruel Intentions."

Phillippe and Witherspoon separated in 2006 and officially divorced in 2008, according to The List. They share two kids, Ava and Deacon.

Both Phillippe and Witherspoon agree that the main reason for them divorcing was simply that they were married too young.

"I think more of the problem was age. When we got together we were so young," Phillippe told Larry King in 2015. "I think it can create issues with two people in this industry because there's so much noise that goes along with it."

In 2017, Witherspoon had a similar answer regarding the end of their relationship. "I got married when I was 23 and I had two kids by the time I was 27," Witherspoon said, "So I don't know, you know, sometimes it's good to know yourself. I would never change anything. I've said to my daughter, I think, you know, [at] 25, you start to know yourself a little bit better."

Just a few months before the beginning of the new millennium, star soccer player David Beckham and former Spice Girl Victoria Beckham got married in 1999.

David and Victoria Beckham
David and Victoria Beckham.Dave Hogan/Getty Images

The whole "love at first sight" concept might seem cliché to some, but that accurately describes exactly how the future Mrs. Beckham felt when she first met her eventual husband in 1997 at a charity soccer game in Manchester.

"Love at first sight does exist," the former Spice Girl wrote in a 2016 issue of British Vogue as she described their meet-cute. "It will happen to you in the Manchester United players' lounge — although you will get a little drunk, so exact details are hazy."

Like the true '90s British royalty they were, the Beckhams held their wedding at Luttrellstown Castle in Dublin, Ireland. The bride even wore an 18-karat golden tiara.

After 23 years of marriage and four kids (Brooklyn, Romeo, Cruz, and Harper), the Beckhams are still going strong, outlasting many of the high-profile celebrity marriages that occurred during their time.

Read the original article on Insider