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Love Stories Of Another Era: Iconic Celebrity Couples From The 80s And 90s

Image Source: s_bukley / Shutterstock

This article talks about the love stories of celebrities from the 80s and 90s, sharing some surprising and lesser-known relationships of that time.

John Cusack and Jami Gertz

John Cusack, a popular figure in the 80s and 90s, was involved with Jami Gertz, a member of the “Brat Pack.” Their romance began in 1983 on the set of “Sixteen Candles,” but it ended before it began. Cusack has since kept his relationships private, while Gertz went on to marry Tony Ressler.

Jay Leno and Sharon Osbourne

Sharon Osbourne, known for her marriage to Ozzy, had a brief affair with Jay Leno. They met by chance at a bar and had a short fling. However, Leno introduced his future wife to Osbourne, ending their fling for good.

Chris O’Donnell and Reese Witherspoon

In 1993, 22-year-old Chris O’Donnell and 16-year-old Reese Witherspoon attended a tribute party together. O’Donnell admitted to having a soft spot for Witherspoon, but she maintained that they were just friends.

Emilio Estevez and Paula Abdul

Emilio Estevez and Paula Abdul married in 1992 but divorced two years later due to differences regarding starting a family. Abdul wanted children, while Estevez, who had children from a previous relationship, did not.

Jennifer Garner and Scott Foley

Jennifer Garner fell in love with Scott Foley while working on “Felicity.” They married in 2000 but divorced in 2003, attributing their failed marriage to the fast-paced nature of Hollywood relationships. Garner later married Ben Affleck.

John Cusack and Melissa Gilbert

Melissa Gilbert used her relationship with Cusack to make her ex-boyfriend, Rob Lowe, jealous. This created a complicated love triangle, as Lowe was Cusack’s best friend at the time.

Jennifer Love Hewitt and Will Friedle

At 18, Jennifer Love Hewitt and Will Friedle developed a romantic relationship, having previously played best friends in a movie. Their romance did not last long and ended soon after becoming public.

Denise Richards and Paul Walker

Paul Walker and Denise Richards hit it off after working together on the movie “Tammy and the T-Rex.” Their relationship became noteworthy due to their prominence in the industry during that time.

Each of these couples had their own unique love stories, showcasing the complexities and unpredictability of relationships in the world of celebrities.Unfortunately, you can’t just put these two beautiful creatures in the same room and NOT expect something to happen. These were the mid-1990s, and Denise Richards was one of the most beautiful and desirable women around. They were a ridiculously stunning couple who enjoyed the limelight for a good while.

Way before he became one of our most hated yet loved characters on “Felicity,” Joey Lawrence was busy galavanting with Keri Russell down the streets of Hollywood. Their short relationship lasted for just under six months and had its share of drama.

Fred Savage gained immense popularity in the late ’80s and early ’90s for his role as the lead in “The Wonder Years.” At the same time, Hewitt was 14 and making a name for herself on Disney’s “Kids Incorporated.” The two young stars eventually crossed paths.

John Cusack and Lili Taylor starred together on “Say Anything.” As it turns out, Taylor wasn’t satisfied with only dating Cusack, as it was reported that she had a bit on the side with D.V. DeVincentis, one of Cusack’s best friends at the time. Though they probably didn’t stay friends after that.

This might come as a shock to you, but during the 1980s, the queen of the Oscars dated the king of the screen for almost five long years. Neeson and Mirren met playing the roles of Gawain and Morgana on the set of “Excalibur” when they were still both unknown.

Before NSYNC became NSYNC, the pop girl group Wild Orchid was a big thing, and Justin Timberlake and Fergie had it going. They were both in the entertainment industry from a young age, which is probably what drew them to one another. Timberlake was just 16 years old, and Fergie was seven years his senior. Age was never a barrier until Britney came along.

Notoriously a bad boy, every single relationship that Charlie Sheen has been involved in reached the tabloids and the headlines. Except for one. Not much is known about his short affair with Robin Wright, and we are here to tell you all about it.

Before he became an A-lister, before his Hollywood royalty days, and before “Thelma and Louise,” Pitt dated his co-star at the time, Juliette Lewis. She starred alongside him in “Too Young to Die?” and they were together for just over four years, despite a significant age difference between them.

It is Conan O’Brien who we must thank for turning Lisa Kudrow into Lisa Kudrow (and Phoebe). As it turned out, Kudrow met O’Brien at an improv comedy class, and as soon as she set her eyes on him, she fell madly in love.We could not have predicted their relationship history.

“O’Brien was the one who encouraged Kudrow to follow her dream and become an actress. And what a great job he did.”

John Cusack and Janice Dickinson

The romance between John Cusack and Janice Dickinson was intense. After ending things with Claire Forlani, and before a short fling with Melissa Gilbert, the two got involved. They reportedly were caught playing adult games in an airplane restroom. Dickinson claimed that Cusack had no sense of humor and that she found him pretty dry.

Jessica Simpson and Jensen Ackles

Jenson Ackles was Jessica Simpson’s first love. Simpson dated the “Supernatural” star when she was 18 years old. It took Simpson a long time to get over Ackles.

Jon Hamm and Jennifer Westfeldt

The love story between Jon Hamm and Jennifer Westfeldt began in the late 1990s and lasted almost two decades. The two ultimately parted ways, with Hamm now engaged to actress Anna Osceola.

Robin Thicke and Paula Patton

Robin Thicke and Paula Patton were together for 21 years until they decided to go their separate ways in 2014. While we are unaware of any current partner Paula may have, Robin is currently seeing model April Love.

Tyra Banks and Seal

Seal and Tyra Banks dated for three months. Their relationship was kept relatively low-key, and besides one event that they appeared together, no one made a fuss of them.

Corey Feldman and Drew Barrymore

In 1989, Feldman dated Drew Barrymore, also known as a child star of those days. The two came together as an item to the Oscars that very same year.

Kate Moss and Johnny Depp

Johnny Depp and Kate Moss were an item between 1994 to 1998. In 2007, Johnny Depp spoke fondly about Kate Moss.

Cher and Tom Cruise

When she was 38, Cher dated a 22-year-old Tom Cruise.“`html

Cher and Tom Cruise

Cher, a successful singer, and Tom Cruise, a budding Hollywood actor, dated for a while but did not manage to turn their story into something meaningful. They seemed more focused on posing for the cameras than making their relationship work.

Gary Oldman and Uma Thurman

In the 1990s, Uma Thurman fell in love with Gary Oldman, who was twelve years her senior. The relationship ended less than two years after they got married, and Uma referred to it as a mistake, possibly due to the age gap.

Madonna and Vanilla Ice

Despite a slight age gap, Madonna and Vanilla Ice dated for under a year. Their relationship ended over disagreements about Madonna’s book, with Vanilla Ice expressing surprise at her openness, despite Madonna’s reputation for speaking her mind.

Tom Cruise and Nicole Kidman

Nicole Kidman and Tom Cruise met during the filming of “Days of Thunder” and married in 1990. They adopted two children before divorcing in 2001, with Kidman admitting that erasing him from her life was challenging.

Molly Ringwald and Anthony Michael Hall

Molly Ringwald and Anthony Michael Hall, stars of 1980s movies “Sixteen Candles” and “The Breakfast Club,” dated briefly before going their separate ways. Both have moved on, with Ringwald married to writer Panio Gianopoulos and Hall to actress Lucia Oskerova.

Richard Gere and Cindy Crawford

Richard Gere, known for his list of previous relationships with famous women, married Cindy Crawford in 1991 when she was in her early twenties, but the marriage ended as Crawford chose to move on from the relationship.

Kim Basinger and Prince

Kim Basinger and musician Prince’s relationship began during the filming of “Batman” in 1989. Both valued the time they spent together, and they worked on music projects, aligning with Basinger’s free-spirited nature.

Winona Ryder and Christian Slater

Actors Winona Ryder and Christian Slater fell for each other on the set of “Heathers” in 1988. Their relationship did not last long, with Ryder considering it just another story in her relationship book, while Slater named her the love of his life.

Reese Witherspoon and Ryan Phillippe

Reese Witherspoon and Ryan Phillippe’s ’90s romance was a rollercoaster. They met while working together and married soon after. However, their relationship eventually ended despite the initial strong connection.

Ryan happened to crash Reese’s birthday party. He turned out to be a very welcomed uninvited guest!

In 1999 they went on to star as doomed lovers in the cult classic “Cruel Intentions” and got hitched a few months later. After rumors and suspicions of Ryan allegedly playing around with other women, Phillipe and Witherspoon called it quits. They have two children together — a daughter named Ava and a son named Deacon, who they continue to happily co-parent to this day.

Brooke Sheilds and Liam Neeson

Despite their 13-year age gap, Brooke Sheilds and Liam Neeson hit it off in late 1991. Their love connection was so intense that Neeson popped the question after only 3 months of dating! However, shortly after the proposal, Liam flew home to deal with his home flooding.

Brooke apparently patiently waited to hear from her fiance but never did. Yep, he ghosted her! Even Brooke Shields can get ghosted, apparently. No one is safe anymore. A few months later, when he got his senses back, he came crawling back to her  and re-proposed, to which Sheilds answered, “NO.” Go, Brooke!

Lance Bass and Danielle Fishel

“Boy Meets World” star Danielle Fishel and NSYNC member Lance Bass were high school sweethearts back in the 90s and even went to prom together. The young lovers weren’t meant to be but remained good friends. After Lance came out as gay in 2006, Danielle was incredibly supportive of her former flame.

Lance recently told Danielle, “I always knew you would completely accept me,” on his podcast “The Daily Popcast with Lance Bass.” Now that’s love! The two eventually found romance in other partners — Bass is married to actor Michael Turchin and Fishel is married to film producer Jensen Karp.

Ellen DeGeneres and Anne Heche

Just mere days before Ellen DeGeneres’s iconic “InStyle” magazine cover where she announced to the world that she was gay hit the stands, she met the late actress Anne Heche at the 1997 Vanity Fair Oscars Afterparty. It was an instant connection and very soon the two skyrocketed into being the most famous queer couple in Hollywood at the time.

Unfortunately, their relationship ended a few years later when Heche apparently left Ellen with no explanation. In a 2001 interview with the “Los Angeles Times,” Ellen admitted, “I’m left with everybody else wondering what happened…I feel betrayed.” Talk about being blindsided!

Matt Damon and Minnie Driver

1997 was a great year for Matt Damon. Not only was his critically acclaimed film “Good Will Hunting” released (for which he would later win an Academy Award for best screenplay) but he also found love.

Matt and Minnie met on the set of the film and started dating. However, any good will (pun absolutely intended) between the two fizzled out when Damon broke up with Minnie by announcing to the world that he was single on “Oprah.” Millions of viewers, including Minnie herself, were shocked by the announcement! Not a cool move, Matt. We wonder what Luciana, his current wife, has to say about it.

Notorious B.I.G and Faith Evans

In a whirlwind romance, the iconic rapper, the late Notorious B.I.G. (also known as Biggie Smalls) met musician Faith Evans on the set of a photoshoot in 1994. A mere eight days later — yes eight days — the two were married! These two knew how to move quickly!

Reportedly, while the romantic relationship between the two began to fizzle out, they remained friends. They even welcomed a baby boy into the world in 1996. Unfortunately, the rapper never got to enjoy being a father for too long as he was killed a mere six months after his son’s birth.

David Spade and Kristy Swanson

It is no secret that Spade is more celebrated for his humor and comedic work than he is for his physical appearance, but that has not stopped him from dating some of the most attractive women in the industry. In fact, the “Saturday Night Live” alum and comedian has a rather lengthy list of former flames.

One of the first on the list is actress Kirsty Swanson.  Spade and Swanson met on the set of the 1996 film, “Heads in a Duffel Bag.” With a title like that, it’s no wonder the film bombed. However, love blossomed between the stars which lasted for almost a year.

Joaquin Phoenix and Liv Tyler

It seems that Live Tyler really believes in love at first sight! In an interview with “The Morning Call,” Liv revealed that, “I fell in love with Joaquin the second I saw him” on set for the 1997 film “Inventing the Abbots.” Sadly, their romance only lasted for three years until the pair split. It’s alleged that Liv was more dedicated to the relationship than he was.

Despite their history, Tyler and Rooney Mara are in a current relationship. After Tyler’s previous relationship with Phoenix, he stated that she doesn’t often fall in love. However, she has had two additional serious relationships since then.

Ted Danson and Whoopi Goldberg

Ted Danson and Whoopi Goldberg began their romance while working on the 1993 film “Made in America.” At the time, Danson was married to Casey Coates for almost twenty years. The affair cost Danson $30 million and his reputation, as Coates filed for divorce after the relationship was made public. After a year and a half together, Danson and Goldberg ended their relationship on a less than amicable note.

Michael Keaton and Courteney Cox

Before Michael Keaton became Batman and long before Courteney Cox was part of “Friends,” they met and fell in love in 1989. After six years together and rumored engagement, they parted ways. Cox later revealed that they still had feelings for each other. With both now divorced, fans wonder if there is a chance for a reunion.

Salma Hayek and Ed Norton

Selma Hayek and Edward Norton met through their shared chiropractor in 1999. The couple dated for a few years before parting ways in 2003. Despite the breakup, they remain on good terms and even attended each other’s weddings.

Thurston Moore and Kim Gordon

Thurston Moore and Kim Gordon’s love story began when they formed the band Sonic Youth in 1981. The two married in 1984, becoming a major power couple in the music industry. However, their relationship fell apart when Moore began a secret relationship with his book editor Eva Pinz, leading to a messy divorce.

Spike Jonze and Sofia Coppola

Sofia Coppola and Spike Jonze met while working on a music video for Sonic Youth. Their friendship turned into a romance, leading to a wedding at Coppola’s father’s vineyard in 1999. Unfortunately, the couple split a few years later, with speculation that Coppola’s film “Lost in Translation” was inspired by their strained relationship.

Carson Daly and Jennifer Love Hewitt

MTV star Carson Daly and actress Jennifer Love Hewitt began dating in 1998. Daly got a tattoo of Hewitt on his leg, but the relationship didn’t last. Despite their breakup, they remained good friends, although Daly was surprised to learn about the breakup from “E! News” rather than directly from Hewitt.

Fiona Apple and Paul Thomas Anderson

Singer Fiona Apple and director Paul Thomas Anderson were seen as the ultimate 90s power couple. They collaborated on various projects but their relationship ended after four years due to negative and toxic elements, which Apple has spoken out about.

Brad Pitt and Jennifer Aniston

Brad Pitt and Jennifer Aniston, one of Hollywood’s most famous couples, were set up on a date by mutual friends. Their relationship became a significant part of pop culture in the 90s and early 2000s.

The end of Brad and Jennifer’s marriage marked the beginning of a tabloid tsunami that would last years of rumors and gossip surrounding the failed romance. The two re-ignited rekindled romance rumors when spotted being very supportive of one another during the 2021 awards season.

Bruce Willis and Demi Moore first laid eyes on one another in July 1987 when… ahem… Demi was still involved with another man. She was engaged to Emilio Estevez at the time. It didn’t take long for Demi to end her engagement with Estevez and jump head-first into a relationship with Bruce. A mere five months after the first meeting, the two eloped in Las Vegas. Moore and Willis divorced after giving birth to three daughters and ten years of marriage.

Gwen Stefani’s band, No Doubt, opened for Gavin Rossdale’s band, Bush, in 1995. The songbirds quickly became love birds, and after a six-year relationship, the two got married. However, it didn’t last as Gavin was engaging in extramarital activities with the family nanny. The two soon got divorced, and Gwen has since moved on with country crooner Blake Shelton.

David Bowie and Iman were together for 26 years before Bowie’s untimely passing. The two first locked eyes on one another in 1990 at a dinner party. In an interview with “Hello Magazine,” Bowie said, “My attraction to her was immediate and all-encompassing… That she would be my wife, in my head, was a done deal.”

Famous magician and illusionist David Copperfield managed to woo supermodel Claudia Schiffer by asking her for assistance during one of his shows in 1993. A year later, the two were engaged but split up in 1999. Many have speculated that the relationship was a long ruse to boost Copperfield’s fame. However, both Schiffer and Copperfield strongly deny this.

Goldie Hawn and Kurt Russell ignited their long-lasting relationship flame while on the set of the 1983 film “Swing Shift.” They have welcomed a son named Wyatt as a sibling to Goldie’s Kate and Oliver from her previous marriage to Bill Hudson. When asked about the key to the pair’s relationship success, Goldie credits the two for never marrying and having time to themselves.

Music icon Billy Joel and supermodel Christie Brinkley met while on a luxurious vacation in the Caribbean in 1983. Joel played the piano on the island where Brinkley and her group were vacationing. The couple tied the knot on a super yacht two years later but divorced due to busy schedules and failed communication.

Pamela Anderson and Tommy Lee’s infamous first encounter was at a New Year’s Eve Party in 1994, where Tommy Lee licked Pamela’s face. Shortly after, they were married. Unfortunately, their private love life became tabloid fodder which ultimately led to their divorce.Hugh Grant and Elizabeth Hurley met when they starred in “Remando al Viento.”

They were together for 13 years before they broke up in 1995. Antonio Banderas and Melanie Griffith first met at the 1989 Academy Awards but only got together in 1995. They were together until 2014. Jude Law and Sadie Frost met on the set of “Shopping” and were married in 1997 but got divorced in 2003. Busy Phillips and Colin Hanks met in college in 1997 and although they broke up, they remained good friends. Alec Baldwin and Kim Basinger got together on the set of “The Marrying Man,” got married after six weeks, and divorced eight years later. Chloe Sevigny and Harmony Korine got together after starring in “Kids” and broke up in the early 2000s. Julia Roberts and Lyle Lovett got married after only three weeks of dating and divorced after two years. Corey Haim dated Alyssa Milano, who was the most famous of his girlfriends during his teen idol days in the 1980s.

Dennis Quaid and Lea Thompson

Lea Thompson and Dennis Quaid dated for a year while working on “Jaws – 3” but never married. Thompson later married Howard Deutch, whom she met on the set of “Some Kind of Wonderful”.

Gwyneth Paltrow and Brad Pitt

Gwyneth Paltrow and Brad Pitt were glamorous couple in the 1980s and 1990s. Their relationship ended due to instability in Paltrow’s life.

January Jones and Ashton Kutcher

January Jones and Ashton Kutcher dated for three years before parting ways in 2001. Jones has expressed that Kutcher was not supportive of her career.

Drew Barrymore and Luke Wilson

Luke Wilson and Drew Barrymore started to date in 1997, but their relationship only lasted until 1999. Barrymore has referred to Wilson as an important person in her life.

Madonna and Sean Penn

Madonna and Sean Penn married in 1985, but divorced in 1989. Both have since moved on, with Penn marrying twice and Madonna once.

Melanie Griffith and Don Johnson

Don Johnson and Melanie Griffith had a tumultuous relationship, marrying and divorcing multiple times. Their second marriage only lasted for five years, during which time they had their daughter, Dakota Johnson, known for her role in the “50 Shades” franchise. Griffith and Johnson ended their love story for good in 1996.

George Clooney and Kelly Preston

George Clooney and Kelly Preston dated in 1988 and even had a pet pig together named Max. After their breakup, Clooney kept the pig and raised it until it died at the old age of 18.

Julia Roberts and Matthew Perry

Julia Roberts and Matthew Perry began dating in 1995 after Roberts made a guest appearance on “Friends”.

The two enjoyed each other’s company for almost a year before deciding to end the romance. It is thought that this was the turning point for Mattew Perry, as his drinking problem is said to have begun slightly after the breakup, but this is all hearsay.

Sandra Bullock and Matthew McConaughey

These two did a very good job of hiding their relationship. So much so, that by the time the tabloids realized they were an item, they had already broken up. Apparently, Bullock and McConaughey were together for almost two years and even got engaged secretly! They met in 1996 and immediately felt the sparks while filming on the same set.

For their own reasoning (they kept this a secret, too), they decided to go on their separate ways; however, they have remained close until today. They are very close friends and make it a point to share it with the world.

Arsenio Hall and Paula Abdul

“American Idol” judge Paula Abdul dated Arsenio Hall, who had his very own show. The two met on the set of a movie and lived hectic lives in the entertainment industry. They met while filming “Coming to America,” a classic Eddie Murphy comedy, and became inseparable.

Even though they broke up, Arsenio mentions that he has only good memories of Paula. They stayed friends, and she even appeared on his show after they broke up. Abdul has since married twice (actor Emilio Estevez and fashion designer Brad Beckerman) but Hall has never married, though he does have one son.

Janice Dickinson and Rob Lowe

Like everyone in the 1980s’, all men wanted to be Rob Lowe, and all women wanted to date Rob Lowe. And Janice Dickinson is one woman who actually did that. 1988 was the year it all happened, though it only lasted a few months.

She was a stunning supermodel who escalated her career and later became one of the judges on “America’s Next Top Models,” in addition to being a successful businesswoman and author. Rob Lowe, on the other hand, is a loved actor, producer, and director, but the 1980s will always be remembered as his peak and pride decade.

Cher and Val Kilmer

Movie stars and musicians of the 1980s and 1990s’, practically lived in the same bubble. They mixed with the same people, mingled at the same parties, and dated the same loved ones. Cher, who was at the peak of her career in those days, set her eyes on Val Kilmer, who later co-starred in “Top Gun” with Tom Cruise.

They were a hot item between 1982 and 1984 and then called it quits. Cher said that Kilmer was much younger than her, which was a big issue back in the day, and that older guys (or guys the same age as she was) just weren’t interesting enough for her.

Michal Jackson and Brooke Shields

Unlike today, at the beginning of the 1980s, things were different, and the number of stars was limited. Not every artist that came up with a new song instantly became famous, whereas today, you don’t need much to be recognized worldwide. Michal Jackson, at the time, was known and loved globally. As was Brooke Shields

He dated Brooke Shields for a while, but apparently, they weren’t both aligned with how they wanted things to go. Jackson proposed a number of times; however, Shields tells a different story and has always claimed that they were no more than two good friends.

Christina Applegate and Brad Pitt

In the 80s, Brad Pitt and Christina Applegate were (like many well-known stars at the time) in the spring of their careers. Pitt just started to walk through the path of fame, and Applegate was breaking through with her role in “Married With Children.”

These two were friends as teenagers. Pitt (together with other future stars such as Jason Priestly) would come to her parent’s house for Sunday lunches. Pitt was even her date to the 1989 MTV Movie Awards, though she left with someone else… awkward! They both went on to other partners eventually, though. Applegate is now married to musician Martyn LeNoble, and Pitt, well… we all know what happened with him.

Image Source: s_bukley / Shutterstock

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