Celebrity Couples From The ’90s That We Shipped So Hard

By Psquared - May 14, 2019

Being in a happy, loving, committed relationship is one of the most rewarding feelings in the world. It’s also one of the most difficult things to maintain. Personality and future goals often conflict, leading to disagreements that tear even the seemingly most joyous couples apart. Since it’s so hard for us to keep our own relationships together, we often turn to movies, songs, TV and all sorts of other media to see and hear about loves that we can live through vicariously.

And these aren’t all just fictitious stories. Sometimes we see famous people finding love with each other, and we root for them. After all, they’re famous! If they can’t make it work, then what hope is there for all of us normies? Sadly, celebrities have just as much trouble keeping their love lives working as we do. But we’ll always have the memories at least. Here are the lovebirds from the ’90s that we loved and wished worked out.

Pamela Anderson And Tommy Lee


This was a celebrity couple that was followed and scrutinized by the tabloids very heavily.

They were one of the most viewed couples in the world, and part of that was definitely a result of a certain tape of theirs that leaked out to the public.

Despite everything, they were a couple that we loved at the time. Tommy Lee was the bad boy drummer, and she was the lifeguard everyone dreamed of. Life was so much simpler back in the ’90s.

Gwen Stefani And Gavin Rossdale


This series of pictures is going to be more difficult to look through than we realized.

We’re not crying, you are. And we don’t blame you. Of course we also miss the pairing of the first man and first woman of alt rock and ska rock respectively.

Remember when Gwen sang songs about being heartbroken over her band’s bassist dumping her, and she wound up being married to this talented hunk for years and years? The fact they broke up, that’s the Tragic Kingdom.

Robert Downey Jr. And Sarah Jessica Parker


Some of you younger readers might be freaking out because this is the first you’re hearing about this.

“Hold up! Are you telling me right now that Tony freaking Stark used to be in a relationship with Carrie from Sex and the City?”

Yup. Those were the days. We don’t know what goes on behind the scenes in their lives and it’s none of our business, but dang, we can dream of a world where they’re still together, can’t we?

Tom Cruise And Nicole Kidman


If you ever get asked who was the biggest celebrity power couple of the ’90s, you show someone this picture.

Of course, in order to do that, it means you’d have to carry this picture around in your wallet at all times.

But to be fair, who doesn’t? Sad, cynical people that don’t believe in love, that’s who! This image encapsulates the 1990s more than a stack of pogs on top of a can of Surge soda. Those were the days.

Brad Pitt And Gwyneth Paltrow


That’s right, we’re just showing you power couple after power couple after power couple here.

Before he was with Jennifer Aniston and Angelina Jolie, Brad Pitt dated his Seven costar Gwyneth Paltrow. Just look at those sweet ’90s cuts they’re rocking.

This couple is as A-list as it gets. Although, to be fair, these two were so famous that anyone they dated would make it an A-list pairing. Brad Pitt marrying a plumber in Des Moines, Iowa would be a power couple.

Bruce Willis And Demi Moore


These two were another major power couple from the ’90s. Although, we’re not sure if that’s the decade this picture was taken in.

Bruce Willis and Demi Moore have simply not aged a day since they both became famous.

You could tell us this picture was taken 25 years ago or 25 years in the future and we’d believe you equally on both statements. Perhaps they’re vampires? That makes their breakup all the more tragic, since they had so much in common.

Gwyneth Paltrow And Ben Affleck


Here’s a couple that many of you might not remember. Ben Affleck is a lucky guy, isn’t he?

He’s dated Gwyneth Paltrow, Jennifer Lopez and Jennifer Garner. So to all of those who thought he wasn’t worthy of playing Batman, his love life proves otherwise.

Who else but Bruce Wayne would be cool enough to be able to date all these amazing ladies? As for Gwyneth Paltrow, she’s now giving new-age-y advice about sticking healing stones in parts of your body, so… that’s cool, we guess.

Johnny Depp And Winona Ryder


Stop it, our hearts can only take so much sweet nostalgia without breaking all over again.

If you’re obsessed with Edward Scissorhands then your heart will fill with overwhelming joy and unimaginable sadness to learn that its stars used to date but are no longer together.

Hot Topic is a store that cashes in on our cherished childhood memories, so how have they not made a line of shirts, book bags, wrist bands and underwear with this picture on it yet?

Richard Gere And Cindy Crawford


Did you chuckle at the picture of Tom Cruise and Nicole Kidman because of how much taller she was than him?

Then you’re probably doubled over in laughter right now at this image. But height isn’t everything in a man, you know?

It’s a cliche that women on dating sites want a man who is at least six feet or taller, but insane talent and breathtaking good looks is enough to land you a stunning super models, so keep your chins up, shorter fellas (because that makes you look taller).

Joaquin Phoenix And Liv Tyler


Some of these ships are so long gone and forgotten that even we don’t remember them.

We’d be so happy to learn that these two were dating today. They are both immensely talented actors, and we love it when talented people wind up together.

They also would make us nerds so happy. One was a key character in Lord of the Rings, and the other is the Joker. That’s two fandoms converging in one awesome couple right there!

Elizabeth Hurley And Hugh Grant


Forget about Kate and William or Meghan and Harry. Back when they were all still kids, the only royal, British couple we cared about were Hugh and Elizabeth.

The fact our two favorite folks from across the pond found love with each other? That was a fairy tale come to life.

The fact it was in a land full of castles? That made it feel even more like a story that Disney would have written. While they broke up, you’ll be happy to hear they’re still friends to this day.

Notorious B.I.G. And Faith Evans


The first couple of hip hop’s love ended in tragedy. Biggie was killed, and his murderer was never caught.

But let’s not be sad at how it ended, but be happy with the time they had together. They collaborated and made music that will last forever.

We should all be so lucky to find love that awesome. Imagine getting to work on artistic pursuits with your significant other that millions still love decades after you’re gone. Those are some serious relationship goals.

Cameron Diaz And Matt Dillon


This couple doesn’t just make us nostalgic for them being together, it makes us miss an entire decade.

In terms of looks, have you ever seen a couple that personifies the 1990s more in one image? That hair! That fashion!

Oh, and they’re both also super cool, and work well together. Remember There’s Something About Mary? Of course you do! It’s a classic! And it can be considered a classic because it came out over 20 years ago. Ugh, where has the time gone?!

Brooke Shields And Andre Agassi


Do you ever meet a couple and have no idea how they wound up together?

Hollywood is a weird and wild place. But it’s not our place to judge. But we can still scratch our heads in utter astonishment.

Brooke Shields at one point was the biggest movie star in the world, and she wound up marrying the bad boy of tennis. That’s a strange pairing no matter how you slice it, but still, we were so used to it and are sad it’s over.

Courteney Cox And Michael Keaton


Did you know that Courteney Cox And Michael Keaton dated for six years from 1989 to 1995?

It’s easy to forget, because they were both intensely private about their relationship. You’ll be happy to know that they parted on good terms.

Courtney Cox said after their breakup that the relationship was important to her and he was a wonderful person. Well, that’s what we expected and hoped to hear from a true Friend while talking about Batman. Yay to amicable splits of people we love!

Ted Danson And Whoopi Goldberg


We’ve seen power couples of music, acting and even one that involved a tennis player (we’re still not and may never be over that).

But do you want a power couple of comedy? Then this is as powerful as it gets.

You know how after a breakup you often try to figure out who “won?” Well, one wound up on the View so we get to see her all the time, and one wound up as an a main character on the awesome Good Place, so who won? All of us.

Reese Witherspoon And Ryan Phillippe


Remember how we said that picture of Cameron Diaz and Matt Dillon personified the decade?

We take it back. These two in this image take that honor. How happy were you to learn that the stars of Cruel Intentions wound up together in real life?

That movie had a sad ending, but real life wound up happier! And yes, they sadly split up, but they had several happy years together, and that’s more than most of us get, so let’s be grateful for the good times.

Britney Spears And Justin Timberlake


We don’t know if they would be considered the first couple of the Mickey Mouse Club, but they are definitely the most famous.

Their relationship is well-remembered, so instead of focusing too much on that, can we focus on what they’re wearing in this picture?

We were all so happy they wound up dating… but were they the best influence on each other. The fact they left the house wearing this shows they didn’t make the best decisions while together. Still… we miss this time.

Jennifer Lopez And Sean Combs


Let’s spill a little out for the demise of the relationship between Jennifer Lopez And Sean Combs.

Have you ever wondered why Sean Combs AKA “Puff Daddy” AKA “P. Diddy” AKA “Diddy” has enough confidence to change his name every other fortnight?

It’s because he once dated Jennifer Lopez AKA “J-Lo” AKA “Jenny From The Block.” That’s the type of influence you’d like to get in love. Someone that makes you believe in yourself, no matter what you’re called.

Will And Jada Pinkett Smith


You know what we love about this celebrity couple from the ’90s? The fact that they’re still together!

There is hope for us all after all! They found a way to make it work, so any of us can!

Granted, they have a slew of famous kids that can get on people’s nerves, but hey, you can’t win at every aspect of life. Ha ha, just kidding. This is Will Smith and Jada Pinkett we’re talking about. They win at life in general.