It really is a funny thing. Even though most of us will never know any famous people it is really easy to care about them. As a result, when two stars enter into a relationship and they seem cute together, the rest of us regular Joes often really hope things will work out for them.
For anyone that is old enough to have lived through the '90s, the decade is full of a lot of reasons to smile. Of course, just like any other era, a lot of people made decisions during those years that were incredibly ill-advised. With all of that in mind, it is time to look at this list of 15 celebrity relationships from the '90s we’re still nostalgic about and 5 pairings that always were a bad idea.
In order for a celebrity couple to be considered for possible inclusion on this list, they first and foremost need to have dated during the '90s, according to public reports. For the purposes of this list, it makes no difference if they also were involved during other decades as long as they haven’t been a couple for a long time. Finally, they either need to have seemed like a good enough couple that people wish things had worked out between them or have come across as a poorly conceived pair right from the start.
20 Bad Idea: Sarah Jessica Parker and Robert Downey Jr.
Today best known for her lengthy run playing the beloved character Carrie Bradshaw on television, Sarah Jessica Parker had already attained a certain level of fame when she dated this man. Also not at the prime of his career during the early '90s when this relationship took place, by then Robert Downey Jr. was known for movies like Weird Science and Less Than Zero.
Together from 1984 until 1991, for a time it seemed like Parker and Downey Jr. might go the distance. However, it wasn’t until years after their breakup that Downey Jr. cleaned up his act in his personal life, so dating a squeaky clean star like Parker made little sense.
19 Nostalgic: Alec Baldwin and Kim Basinger
As one of the stars of 1989’s Batman movie, Kim Basinger’s career was on fire when the '90s began and near the end of the decade, she won an Oscar for her work in the film L.A. Confidential. Also, no slouch during the decade, starring in '90s movies like The Hunt for Red October, The Getaway, and The Juror turned Alec Baldwin into a bankable leading man.
Married from 1993 until 2002, when Basinger and Baldwin broke up they had a highly contentious divorce, to say the least. That said, given how gorgeous these two were as a couple, remembering how they lit up the red carpet whenever they walked together takes us back.
18 Nostalgic: Gwen Stefani and Gavin Rossdale
First able to attain fame in the '90s as the lead singer of the band No Doubt, at that time Gwen Stefani shared the spotlight but she certainly was the group’s main star. Another example of a Rock ‘N’ Roll lead singer who captured the world’s attention during that same decade, Gavin Rossdale was the perfect frontman for the popular group Bush.
A long-lasting couple, Rossdale and Stefani started dating in 1996 before they got married in 2002. Even though they got divorced recently it seemed like they led separate lives for a while before then. While Stefani is currently with Blake Shelton and they seem happy together, we fondly remember the years in which she and Rossdale were rock royalty.
17 Nostalgic: Marilyn Manson and Rose McGowan
Among the most divisive celebrities in the world during the '90s, when Marilyn Manson first rose to fame he accumulated loads of highly loyal fans and just as many passionate detractors. On the other hand, Rose McGowan never had to deal with negative headlines as she starred in '90s films like Scream, Phantoms, and Jawbreaker.
For anyone that remembers how incredibly controversial Marilyn Manson was at the height of his fame during the '90s, the idea that people would feel nostalgic about him is pretty incredible. Nevertheless, Manson and McGowan were such a striking pair together that they have gone down in history together.
16 Bad Idea: Pamela Anderson and Tommy Lee
Someone who turned a lot of heads when she began starring in the show Baywatch, during much of the '90s Pamela Anderson was one of the most talked about stars in the world. Definitely a really big deal in his own right, as a member of the legendary band Mötley Crüe, Tommy Lee took the music business by storm for many years.
Married from 1995 until 1998, Anderson and Lee had a whirlwind relationship and even got back together in 2001 and 2008. Clearly, who people who genuinely love one another, they simply haven’t been able to make things work. As a result, we can only imagine how painful it has been for both of them to break up so many times.
15 Nostalgic: Will Friedle and Jennifer Love Hewitt
An actor that many people grew to love when she starred in the show Party of Five, Jennifer Love Hewitt then went on to star in movies like I Know What You Did Last Summer and Can't Hardly Wait. Much more of a television star throughout his career, for an entire generation of people Will Friedle will always be remembered as Boy Meets World’s lovable goofball Eric Matthews.
A pair of extremely likable actors who starred in a little-seen movie called Trojan War together, evidently they grew to care for one another too. A couple during 1997, they looked so sweet together that we can’t help but smile thinking about them.
14 Nostalgic: Spike Jonze and Sofia Coppola
As the daughter of a legendary film director, Sofia Coppola may have felt like she had a lot to live up to but as the person behind films like Lost in Translation and The Beguiled she blazed her own trail. One of the most unique figures in Hollywood, Spike Jonze helped bring the show Jackass to life and also directed movies like Being John Malkovich, Adaptation, and Her.
Definitely not the kind of celebrities you’d expect to see regularly grace the cover of magazines, these two still made quite the photogenic pair. Due to the fact that both directors are true artists and they embrace a similar style, Jonze and Coppola seemed so perfect together that it is sad they weren’t able to last.
13 Nostalgic: Courteney Cox and David Arquette
Probably one of the most unique stars around, David Arquette never seemed like the typical celebrity but he was fun to watch in movies like Buffy the Vampire Slayer, Never Been Kissed, and Ravenous. As the star of arguably the most popular '90s sitcom, Courteney Cox's time on the show Friends turned her into an internationally known comedy star.
Forever memorable for their roles in the hugely popular horror film series Scream, Cox and Arquette made quite the pair on and off the big screen. Married from 1999 until 2013, it has been really great to see how supportive of each other this unlikely pairing has remained since their breakup.
12 Bad Idea: Madonna and Dennis Rodman
At the height of Dennis Rodman’s NBA career, the man who was known as The Worm had built a reputation as the bad boy of basketball due to his rebellious behavior. A singer who absolutely deserves to be considered a legend, throughout much of her career Madonna was known for being at the vanguard of pop culture.
Considering that Madonna had a history of getting involved with cutting edge celebrities, her 1994 fling with Rodman made a certain level of sense. However, we now know that Madonna was very much on the rebound at the time because she’d dated Tupac prior to that and he’d broken up with her in a letter during his time in prison. Given her emotional state at the time, taking part in a high profile and short-lived relationship seemed ill-advised.
11 Nostalgic: Joshua Jackson and Katie Holmes
Back when the show Dawson’s Creek first began airing, it was abundantly clear that the show’s producers wanted fans to invest in Dawson and Joey ending up together. Despite that, by the time the series came to an end, many people would have been much more excited to see Joey end up with Pacey.
Perhaps that is the case because the actors who played those characters, Joshua Jackson and Katie Holmes, clearly shared chemistry. In fact, as Dawson’s Creek fans know, Holmes and Jackson briefly dated and it is a shame their relationship fizzled out.
10 Nostalgic: Claudia Schiffer and David Copperfield
As one of the most successful models of all time, in her prime Claudia Schiffer was such a big star that it often seemed like she appeared on the cover of a new magazine every single month. Also a pretty big deal at that time, at one point Forbes magazine even described David Copperfield as “the most commercially successful magician in history.”
Let’s be completely real here. When you look at a photo of Claudia Schiffer and David Copperfield together they seem like an incredibly unlikely pairing. Married from 1994 until 1999, the fact that Copperfield wound up with Schiffer all those years ago gave outsiders a reason to believe in romance that they won’t soon forget.
9 Nostalgic: Iman and David Bowie
From one entry about a successful model to another, this time around we are going to look at the love life of the incredibly gorgeous woman known as Iman. As the man who gained Iman’s affections for many years, David Bowie released so many hit songs over his decades-long career that he almost seemed like he could do no wrong musically speaking.
Married from 1992 until 2016, David Bowie and Iman always seemed to be entirely smitten with one another. In fact, the only thing that tore them apart was Bowie’s demise which surprised many of his fans because it marked the end of his recording career and his storybook romance with Iman.
8 Bad Idea: Whitney Houston and Bobby Brown
First introduced to the world as a member of the R&B singing group New Edition, it didn’t take long for Bobby Brown to become popular enough to go it alone as a solo artist. Easily one of the most popular singers in the world throughout the '80s and early '90s, to say that Whitney Houston had the voice of an angel somehow feels like an understatement.
Married from 1992 until 2007, Houston and Brown may have seemed like a power couple at first but during their time together both of them struggled greatly with addiction issues. While it is clear that both of them share responsibility for their problems, it also is obvious that they weren’t able to help each other beat their demons.
7 Nostalgic: Notorious B.I.G. and Faith Evans
During his life, The Notorious B.I.G. attained so much respect in the rap world that there are few artists that could even be considered his peer. In fact, since he tragically had his life taken his legacy has only become more celebrated. Another extremely talented vocalist, Faith Evans performed on several hit songs and worked with several celebrated artists over her career.
Married from 1994 until The Notorious B.I.G.’s 1997 passing, he and Faith Evans seemed to truly love one another. For that reason, when she performed on the song “I'll Be Missing You” which was a tribute to her deceased husband it broke the world’s heart.
6 Nostalgic: Julia Roberts and Matthew Perry
One of the most bankable stars in the history of Hollywood, throughout her career Julia Roberts starred in so many beloved movies that trying to list them here would be a fool’s errand. Never able to reach those same levels of fame, Matthew Perry still earned his place in entertainment history as the star of the much-beloved sitcom Friends and several movies.
Truly a hilarious human being, Matthew Perry stands out in any crowd but one of the biggest parts of his appeal is that he always seems like a regular guy. As a result, the fact that he briefly dated Julia Roberts after she appeared in an episode of Friends still surprises us today.
5 Nostalgic: Jennifer Lopez and Sean Combs
The man who seemed to have the music industry on a leash for many years, to this day there are few businessmen and performers who have been more influential in the industry than Sean Combs. That said, it could be argued that Jennifer Lopez belongs on that list as she released loads of popular music and gave people a path to follow as an actor and dancer.
Clearly two people who were powerhouses in every area of their lives, it made perfect sense that Lopez and Combs were attracted to one another. If only they could have made things work out, it is amazing to think about what they could have accomplished as a couple.
4 Bad Idea: Michael Jackson and Lisa Marie Presley
As the only daughter of the Rock ‘N’ Roll legend Elvis, Lisa Marie Presley has spent her entire life in the spotlight to a certain degree. One of the world’s most talked about people since his childhood, from the time Michael Jackson rose to fame alongside his brothers paid attention to virtually everything he did.
For those reasons, most observers were completely surprised when Jackson and Presley got married in 1994. Only together until 1996, both of them said many positive things about one another in the years after that. However, they never seemed to share even the slightest bit of chemistry and they are remembered as an oddity.
3 Nostalgic: Matt Damon and Minnie Driver
An actor who has found steady work since the late '90s, Minnie Driver has been incredible in movies like Grosse Pointe Blank and Owning Mahowny in addition to TV series like The Riches. Somehow even more successful, throughout his career Matt Damon has starred in blockbusters like the Oceans and Bourne franchises and a long list of acclaimed films.
If you are anything like us, every once in a while you will find yourself hoping that actors who portrayed a great couple onscreen would find love in their real lives too. For that reason, we will always wish that Damon and Driver, who played an incredible couple in the movie Good Will Hunting and dated in real life, had gone the distance.
2 Nostalgic: Justin Timberlake and Britney Spears
Often referred to as the Princess of Pop in the past, it is hard to argue that Britney Spears didn’t deserve an accolade like that given how hugely popular she was during the '90s. In fact, there were only a select few pop music acts from the '90s that were remotely close to being on the same level as Spears, including the group NSYNC, of which Justin Timberlake was a member.
As two people who were uniquely positioned to understand each other’s lives, Britney Spears and Justin Timberlake seemed like the perfect couple from the outside looking in. As a result, Bravo even referred to their 2002 breakup as the “end of an era” and we couldn’t agree more.
1 Nostalgic: Bruce Willis and Demi Moore
First able to find success in the '80s as a member of The Brat Pack, during the following decade, Demi Moore cemented her legacy as an incredible actor. Also able to take Hollywood by storm in the '90s, Bruce Willis starred in so many box office behemoths during that decade that he has to be considered one of the biggest movie stars of all time.
Truly an example of two superstars who managed to find love together, Bruce Willis and Demi Moore were married from 1987 until the year 2000. While they couldn’t make things work romantically speaking, it is still clear that they care deeply about one another whenever they occasionally appear together. That fact only makes us more nostalgic for the years in which they walked red carpets as a couple.
Sources: Forbes, Bravo, Cheat Sheet, Hello Giggles, Independent, Daily Mail