All these photos were taken before Instagram came roaring into the world and before filters were what we call modern makeup. The all-time favorite sitcom “Friends” was just introduced, and Tom Cruise was still strongly hooked on Nicole Kidman. Sit back, take a scroll, and remember to periodically go “Woah, I can’t believe it was THAT long ago!”
Charlie Sheen and Nic Cage
While it's fair to say that both of these men – Nic Cage and Charlie Sheen – are fine enough actors, you have to admit that putting them in the same room seems like a recipe for disaster. Of course, this picture was taken in 1990, which was long before either of these men lost the plot and while they were still climbing the ladder of success.
They're just here having a little bit of fun at the party for Guess? Parfum's US tour. We'll be honest; that doesn't mean anything to us, but they sure do throw a bash if this picture is any indication.
Cameron Diaz and Matt Dillon
"A Kiss Before Dying," "Singles," and "There's Something About Mary" are only some of the movies Matt Dillon is recognized for. He might have been happily (or not so happily) married in the movies he starred in, but in real life, the facts are slightly different. 1995 was the year for Matt Dillon and Cameron Diaz.
The relationship lasted for three years, and the two decided to break up in 1998. Rumors say Cameron wanted to take the next step in life together with Dillon. He, however, was nowhere near that headspace. These days Cameron is investing her time in her family and other endeavors, and Dillon is still acting.
Tupac Shakur
During the 1990s, Tupac was known for many things, however, the most noticeable thing in his life back then was his love interests. Madonna dated the late rapper Tupac Shakur in 1993 after they were introduced by Rosie Perez at the Soul Train Awards. However, their relationship did not last, and Tupac reportedly ended things with Madonna in a letter while he was locked behind bars in 1995.
Tupac Shakur was listed in the Guinness Book of Records as a top-selling hip-hop artist, with over 70 million records sold all over the world. A record that hasn't been broken until this day.
David Bowie and Iman
We are always touched when the world loses a legend, however, we can't hide the fact that when the world lost Bowie, we were devastated. One of the most successful showbiz couples of the 1990s has got to be David Bowie and Iman. The power pair 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.” Can someone pass us the tissues, please?
Happy Family
This photo of Donald Trump in his younger days proves he is in possession of a softer side, one brought out by his kids and then-wife Ivana. Family photo for the win – one look at their happy faces, and you can tell love is in the air behind this snap.
Many years have passed since this photo was taken, and many things have changed. Donald and Ivana are no longer together, and he became not only a businessman but a politician too. The Trump family has adorned our newspaper headlines on many occasions and has become one of the most famous families in America.
Edward Furlong
Edward Furlong was once one of Hollywood’s most promising stars. The child star gained fame in the early ‘90s as young John Connor in the action film “Terminator 2: Judgment Day” and in the horror movie “Pet Sematary Two.” But continents away, Edward also made a name for himself when he released an album in Japan called “Hold on Tight,” which featured his cover of the Doors’ hit “People Are Strange.” He also appeared in a Japanese commercial for instant Hot Noodle soup.
Unfortunately, being famous in Japan wasn’t enough to sustain his career in Hollywood, and as the years went by and vanished, so did his fame and glory. He has done things here and there but never reached the success he aimed for.
Tom Cruise and Nicole Kidman
Ah, can it get any more 90s power couple than these two? We think not. Cruise and Kidman enjoyed a two-year rule as the king and queen of Hollywood, gracing nearly every red carpet with their presence. But things eventually started falling apart. At the beginning of 2001, the two announced that they were going on their separate ways.
By August of 2001, the two were officially divorced, citing irreconcilable differences, leaving Hollywood on the hunt for a new couple to worship. These days Cruise is still working hard and memorizing lines for his next movie, and Kidman is doing the same.
Jennifer Aniston
If it was the nineties and you looked at a rumor mag or the papers, you had a pretty good chance of seeing a picture of Jennifer Aniston. She was huge because of “Friends,” being married to Brad Pitt for a while, and... some other reasons, probably.
Despite just being one of six members of the main cast of one of the most popular franchises ever, she seemed to get all the attention. This picture has her in a little black dress in 1997 as she arrives at a Cosmopolitan Magazine party, looking ready to make everyone around her pleased to be there.
Gwyneth Paltrow and Giorgio Armani
The lady in this pic is Gwyneth Paltrow, but who's the older gent getting comfortable with her? How dare you not know the legendary face of Giorgio Armani, a man whose name is practically synonymous with high fashion? Well, that's him, and if there was any picture that made a lot of people think about starting a fashion company, this is it.
Paltrow has squeezed herself into some tight leather pants and sat on the floor with a drink and a cig, which is when the fashion legend came over for a picture. Was she a muse? Was he designing new stuff for her? Maybe. Or maybe it's just two famous people being famous together.
Kirk Cameron
Kirk Cameron was all over the screens in the 1990s. He took his first footsteps in the industry, starring in "Two Marriages" when he was just thirteen years old. He then went on to bigger things and became globally known after playing the role of Mike Seaver on "Growing Pains."
Then the 1990s were over, and with a heavy heart, we must say, so was his career. Although he has appeared in many television shows and numerous films (the most recent one in 2022), Kirk never managed to reach the top and remains to this day a small-screen, quite forgotten kind of star.
Pamela Anderson and Tommy-Lee
One of the most infamous couples of the 90s was undoubtedly Pamela Anderson and Tommy Lee. The two had a rather off-beat first encounter. After locking eyes at a New Year's Eve Party in 1994, Tommy Lee licked Pamela's face. Apparently, that swept her off her feet! Guess different people get turned on by different things, what can we say?
In what only can be described as a whirlwind romance, Tommy and Pamela were married only days later! Unfortunately, the pair's private love life became tabloid fodder which ultimately led to their marriage breaking down. Controversial videos were involved, and... well, we will spare you the details.
Gary Oldman and Uma Thurman
Uma Thurman is one you just gotta love. And Gary Oldman thought that, too, back in the 1990s. Oldman was Thurman's first true love, as she once said in an interview. She said she was young and inexperienced, and unsurprisingly their relationship ended when it did, less than two years after they tied the knot.
Uma even took it a step further by adding that this was the mistake of her life. He was 12 years older than her, and that was bound to cause friction at some point. Uma Thurman grew into her glory, leaving Gary Oldman as nothing more than an old page in her book.
Cindy Crawford
Cindy Crawford is seen here at the Emmy Awards in 1992 with the then mega-star Jason Priestly. Crawford was not nominated for any award that year, and neither was Priestly, however, she hit a fancy fashion high note in this get-up. With a touch of black-and-white ‘80s nostalgia, Crawford’s tuxedo-twist ensemble boasts a satin bustier and a high slit.
In the 1990s, Crawford was one of the most famous supermodels alongside big names such as Linda Evangelista, Naomi Cample, and Claudia Schiffer. Priestly was the loveable Brandon Walsh on "Beverly Hills 90210." While the two were the biggest names in Hollywood at the time, Crawford preserved her title for years, which is not exactly what we can say about Priestly.
Sting and Madonna
We bet that you know at least one or two on sight, and you might even be able to get three of them. From left to right is Tupac Shakur – probably the easiest to identify – followed by Sting, Madonna, and Ingrid Casares. Three musicians and an actress/businesswoman at the same table? It has to be a music event, right? Wrong, somehow.
This was taken at a dinner party for Gianni Versace in 1994, and all four of these people were living large in the limelight. We're a little surprised that Sting went with nothing but a wifebeater, but you do you, buddy.
Drew Barrymore and Luke Wilson
Many couples start their love story on the sets of a movie, and so did Luke Wilson and Drew Barrymore. "Home Fries" and "Best Man" were where it all began for these two. They started to date in 1997 but only lasted until 1999. Barrymore has said in a number of interviews that Luke Wilson is one of the most important people in her life and that she has been privileged to have known him.
Luke Wilson became worldwide famous not for his relationship with Barrymore but for his roles in "Legally Blonde," "Skeleton Twins," and many other great hits.
Tori Spelling and Jennie Garth
At the 47th Annual Emmy Awards in 1995, Tori Spelling and Jennie Garth were the hottest names in the industry. These were the days of "Beverly Hills 90210" when everyone, and we mean everyone, wanted to be either a Brenda or a Kelly (or a Donna). If you were the monarch of the gang or queen of the prom, you were Kelly, however, if you were the innocent blonde or the daughter of the producer, you were Donna.
The two met on the set of "Beverly Hills 90210" and ended up being very close friends off-set too. Although the daytime drama packed up in the early 2000s, Garth and Spelling remain friends 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 three 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!
He came crawling back to her a few months later and re-proposed, to which Sheilds answered, "NO!" Go, Brooke! Neeson may be bad in relationships, but when it comes to the screen, he is an incredible actor with remarkable roles. If only he could be like that as a partner!
Joan Rivers
If you're Joan Rivers, you get to hang out with whomever you so choose. And, true to that fact, here she is at a Gossip party at Club USA in New York on April 28th, 1993. She's hanging out with a couple of studs who have decided it's warm enough to go shirtless.
Joan Rivers was a comedian and television personality, which means she probably knew the best way to cut loose, even if that meant you had to spend time with handsome, muscular men with nice smiles. We guess that's just how it was done back in the last decade of that century.
Katie Holmes
There are many published photos of the beautiful Katie Holmes. Most photos are from her early days on "Dawson's Creek" and from the time she gave a remarkable performance in the 2005 version of Batman, "Batman Begins." Other famous photos are with her more famous ex-husband, Tom Cruise.
Her relationship with Cruise was one of the most talked about ones in Hollywood and is even still talked about today. There are very few photos of Katie Holmes from her very young days, especially with other members of her family, like this one of her and her sister, with whom Katie has a very close relationship.
Shania Twain
Having some trouble placing those two? We're talking about the two on the left, but the way. We have no idea who is on the right. Those are a couple of country music standouts. Shania Twain is in the middle, and if you're a fan of her music, you probably already know that. Who is the majorly-mulleted man sitting to her right? It's Billy Ray Cyrus, a genuine hitmaker (with one hit, at least).
Yes, these days, he's more famous for being Miley Cyrus's father, but “Achy Breaky Heart” was always being played. This pic comes from the 34th Annual Academy of Country Music Awards in 1999.
Carson Daly and Jennifer Love Hewitt
If you were a TRL-loving teen, then you know all about the iconic relationship between MTV star Carson Daly and 90's actress Jennifer Love Hewitt, star of "I Know What You Did Last Summer." The two got together in 1998 and were so loved up that Daly got a tattoo of Jenniffer on his leg. Talk about commitment!
As we all know, relationship tattoos often jinx a relationship. Carson and Jennifer called it quits. While the two remain good friends, Carson was shocked to discover the news of his break-up from "E! News" and not from Jennifer directly. Shocking indeed!
Liam Gallagher
Since 1991, this man, Liam Gallagher, and his brother Noel have been revamping British music with their band Oasis and other projects. It kind of looks like Liam is trying to use a classic Beatles look and adjust it for nineties fashion aesthetics, but we're not really sure how well it's working.
The picture is from 1998, one of the few years he was married to actress Patsy Kensit, and it looks like he's having a ton of fun in this picture. Was this before or after he got into a fight because of a scone on an airplane or something ridiculous like that?
River Phoenix and Others
Here we see a bunch of people partying with PETA. We've got, in a left-to-right manner, River Phoenix, Kate Pierson, KD Lang, Chrissie Hynde, Lene Lovich, Liza Minelli, and Fred Schneider posing nicely for this organization in a New York event.
We assume the roast beef was done to perfection. (KIDDING, gosh.) We don't actually know how most of those people are in real life, but if they're into animal rights they can't be all that bad. In the 1990s, River Phoenix was beloved and destined for great things until he tragically lost his life at too early of an age.
Thurston Moore and Kim Gordon
Thurston Moore and Kim Gordon were the ultimate romantic Rock and Roll royalty. The two musicians met, fell in love, and formed the iconic band Sonic Youth back in 1981. Moore and Gordon even tied the knot in 1984, making them the coolest married couple around. They were a huge success, however, it didn't last very long.
Unlike a love song, the rockers' relationship untimely turned very sour. It turned out that Thurston was secretly seeing his book editor Eva Pinz. Kim discovered the truth when she noticed suspicious texts on Thurston's phone. Sonic Youth imploded, and the couple's relationship ended in a messy divorce.
Rob Lowe and Christian Slater
After the shooting has wrapped, what are you to do as a young working actor but grab some cigars and start puffing to celebrate a job well done? That's what was going through the minds of actors Rob Lowe and Christian Slater during an afterparty at The Greek Theatre in Los Angeles.
They have a few friends around them, but if they're noteworthy names, you'll have to figure them out for yourself. These two actors are all smiles, and in 1996 they knew that the career ahead of them was about to make their names even bigger. And they both succeeded, more or less.
Natalie Portman
The stunning actress was already famous at the time of this photo. Natalie Portman began her film career at the ripe old age of 12, and though fame infiltrated her early life, Natalie was still able to enjoy the simpler things like going to prom. She was born in Israel in 1981 and moved to America at a very young age.
Portman has a remarkable career and is considered one of the most desired actresses in the industry. She has for sure left a mark in Hollywood following her astonishing performances in "Black Swan," "Star Wars," and the list just goes on and on.
Naomi Campbell
Naomi Campbell is one of the most prolific models in the world, after establishing herself at just fifteen years old as a leader in the modeling industry. She was one of the six models of her generation declared a "supermodel" by the industry and the press. Here she is pictured holding hands with fashion queen Donatella Versace and followed by Leonardo Dicaprio.
In the 1990s, Campbell broke barriers for so many, becoming the first black woman to achieve such awareness because of her dazzling looks. Alongside big names like Cindy Crawford and Christy Turlington, Campbell was one of the leading icons of the era and grew to set fashion trends and awareness.
Ewan McGregor
While Ewan McGregor's most famous role – that of Obi-Wan Kenobi in the "Star Wars" prequels – wouldn't start for a few years after this picture was taken. He is seen here in 1997, taking his first steps up the ladder of success just as "Brassed Off" was released. From there, the possibilities were endless.
McGregor has grasped numerous awards for several roles he played and has been praised for his charity. In the 1990s, he rose to fame with the release of the movie "Shallow Grave," however, he is most famously known and appreciated for his astonishing role in one of the most successful yet controversial movies of that time, "Trainspotting."
Julia Roberts and Benjamin Bratt
When Julia Roberts was the number one woman in Hollywood, and when "Friends" just began to make it big, Roberts' heart belonged to Matthew Perry, better known as Chandler from "Friends." She even gave a guest appearance on the show. Die-hard fans might remember her as Susie from the two-parter of the second season. Unfortunately, this relationship, too, didn't last.
In 1998, Roberts met her next romantic partner, actor Benjamin Bratt from "Law & Order," and gave a little cameo in his show too. The two dated for quite some time and even went to the 2000 Oscars together where they got this sweet picture.
Chris O'Donnell and Reese Witherspoon
In 1993 Chris O'Donnell was 22 years old, and Reese Witherspoon was barely 16. She accompanied O'Donnell to a tribute party following his appearance in the movie "Scent of a Woman." There was a bit more going on than just accompanying one another.
Chris O'Donnell had reportedly admitted at the time that he had a soft spot for Whitherspoon and thought she was very nice. She, on the other hand, never spared a compliment and said that they were just friends. Chris O'Donnell went off to star in NCIS: Los Angeles, the NCIS spin-off, and Reese Witherspoon adorned our screens in "Legally Blonde" and "Sweet Home Alabama."
Jenna Von Oÿ
Jenna Von Oÿ is best known for her role as Dorothy "Six" LeMeure in the 1990s hit "Blossom, " and her role in the "Moesha" spin-off series, "The Parkers." She has since turned to writing and music. Fun Fact: co-star, Ted Wass, revealed that Jenna had a unique drink that she would make to get into character as the fast-talking Six LeMeure.
He said, "Jenna would mash up all this candy—malted milk balls, M&Ms—in a coffee cup, then fill it with Coke or strong hot coffee." Now that explains how she was so hyped up all the time! And here we thought she was naturally that talkative.
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!
Kylie Minogue and Lenny Kravitz
If these two walk in the door, people notice. But who are they? You probably already know. On the left, we have the thrilling Kylie Minogue, best known for her genre-defining pop songs. On the right, we have Lenny Kravitz, who either has a ginormous head or is a lot closer to the camera than Kylie.
He also has immense dreads and a head that could comfortably house a classroom of engineering students. Kravitz's most famous song (probably) is “American Woman,” but it seems that he's made the change to Aussie gals. Honestly, is Kylie a tiny person? Or does Kravitz have the biggest head in the world?
Brad Pitt and Jennifer Aniston
We could not have a 1990s list (of any kind) without mentioning the power couple of the decade. Possibly THE it-couple of the 90s (and yes, the early 2000s) and America's sweethearts were, of course, Brad Pitt and Jennifer Aniston. One of the most famous celeb couples in Hollywood history began in a rather ordinary way. The pair was set up on a date by their managers. The rest was pop-culture history.
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 sparked some rekindled romance rumors when spotted being very supportive of one another during the 2021 awards season.
Liv Tyler
What does a young, famous, attractive person do when she's bored? Hang out with other young, famous, attractive people, of course! Here we see Liv Tyler – daughter of Steven Tyler and famous for her roles in “Armageddon” and the "Lord of the Rings" trilogy – and Stella McCartney partying at a Versace party in New York City.
Stella is the daughter of Paul and Linda McCartney, and she works primarily as a fashion designer. While we can't speak about how close these two really were, it certainly looks like they were friendly. Being born to famous rock musicians has got to come as an advantage.
George Clooney and Kelly Preston
We bet you never knew that Mr. Nespresso, George Clooney, took his first Hollywood footsteps as a guest appearance on the 1980s show "The Facts of Life." Well, he did, and at the same time (and we didn't know this until researching for this article), he dated Kelly Preston before she went off and married John Travolta.
They dated for a while but didn't last too long, as we now know. During their time together, though, they moved in together and even raised a pet pig! After the two parted ways, Clooney kept the pig and raised it until it died of old age in 2006.
Celine Dion
Though it might be hard to believe, famous songstress Celine Dion was, at one point, twenty-seven. This picture has her celebrating her birthday with her late husband, Rene Angelil, to whom she had been married for about a year at the time. For our younger readers, Angelil was also her manager.
Rene was Dion's first and, so far, only marriage, while Dion was the second woman to be attached to Rene. Despite not even being part of movie history as a singer for “Titanic” at the time, Celine Dion was already well-known and respected. Even in this picture, she looks like she's about to burst with a song.
Mariah Carey
Who knew that Mariah Carey had such a noteworthy height? This tall drink of water is seen being helped down from a long step at the 8th-anniversary party for the Z100 radio station held at the Palladium Club.
Nowadays, she's most well-known for being the voice behind the sound of the holiday season hit, “All I Want for Christmas Is You.” However, she's had a long career doing all sorts of things, including partying with lots of other famous people. All the while, she was so tall that she had to be helped down while wearing heels – she's five-eight without any extra footwear.
Gwyneth Paltrow and Brad Pitt
In the 1980s and 1990s, you couldn't get better looking than Brad Pitt and Gwyneth Paltrow. They were the most glamorous couple of that era and were adored by all. They dated for two years, which at the time seemed like a lifetime, as many Hollywood relationships never reached the end of the first year.
A few years later, Gwyneth Paltrow admitted that their relationship ended because she was in a very unstable time in her life and that she practically messed it up. You never know; maybe Paltrow could have saved us the whole Anniston-Jolie story if she had stuck around.
Michelle Williams
During the 1990s, Michelle Williams was climbing the ladder of success. During that era, Williams starred in "Dawson's Creek," one of the most talked about shows that aired back then, and in addition, she contributed her talent to other shows that were slightly on the controversial side. When the 2000s kicked in, she was at her peak.
She nailed it on the huge hit "Brokeback Mountain," and since then, she has been unstoppable. In this photo, she is seen at the 1999 Emmy Awards, where she went home empty-handed, however, since then, she has grasped more than 50 wins of several awards.
Hugh Grant and Emma Thompson
Here we have Hugh Grant wrapping up Emma Thompson at a wrap party for their movie “The Remains of the Day,” which starred Thompson. Grant might have had a more minor part, but he was in it all the same, and the way he's looking ahead makes it seem like he knows how good his career is going to turn out.
That's not to say Thompson wasn't right there with him – she's one of the most lauded women in acting history. She has won awards aplenty and was even married to the famous Sir Kenneth Branagh for a time.
Shannen Doherty
If there was one troublemaker during the 1990s, it has to be Shannen Doherty. She is known, loved, and hated for so many things, some related to television and movies, and some to her scandal-ridden life. She is known being Brenda Walsh on "Beverly Hills 90210" and for playing Prue Halliwell on "Charmed." She is also known for her marriage to Ashley Hamilton, son of actor George Hamilton, which only lasted for about six months.
After her marriage to Ashley went bad, Shannen went on to have a relationship with another celebrity with a bad reputation — Rick Salomon, who was notorious for his dubious ties to Paris Hilton. As for her career, Shannen has starred in a few movies, none of them being too successful.
George Michael
With both a popular band and a staggering solo career, of course, George Michael was going to enjoy his time in the clubs in the nineties. This pic is from back at the beginning of the decade, 1990, and he wasn't about to let the good times stop rolling just yet. He was about to reach the peak of his career.
George Michael's solo album, which was released when the new decade came roaring in, sold more than 8 million copies bringing the artist to new heights. He became an icon of an era until his unexpected death on Christmas day, 2016. He is considered one of the best musicians of all time, and by looking at this photo, one of the best dancers too.
Bijou Phillips
Bijou Phillips is an actress, model, and singer. You might remember her from her breakthrough role in the movie "Almost Famous" where she starred alongside a very young Kate Hudson. Many years previous to her marriage to her current husband, she dated none other than Leonardo DiCaprio, known for this neverending list of dates.
Bijou Phillips’ acting career got a great start in "Black and White," a film that launched the young model's career. The last time we saw her on the screen was in 2013. Being the daughter of John Phillips and Genevieve Waite, she will probably stick to music in the foreseeable future.
Michelle Trachtenberg
Born in 1985, Michelle Trachtenberg debuted on Nickelodeon with a part in just one episode of "Clarissa Explains It All." Soon, she won the role of Nona Mecklenberg in Nick’s "The Adventures of Pete & Pete," which ran until 1996. She was nine when she scored that gig!
Trachtenberg was a Nick star for years until she moved on up to adult showbiz. Playing Buffy’s sister in the fifth season of "Buffy the Vampire Slayer" was the role responsible for transitioning her career. Michelle cemented her place in teen idol history by starring as Georgina Sparks in the cult classic early series "Gossip Girl" and as Casey Carlyle in the figure-skating drama "Ice Princess."
Bill Clinton
The 42nd president of the United States, Bill Clinton, served two terms from 1993 to 2001. While he was in office, America enjoyed an unprecedented time of economic expansion, record job creation, and a decline in poverty. White House reporter Helen Thomas said of Clinton, “He has brought on the greatest prosperity we have ever known, and he doesn’t get the credit for it, and that’s too bad.”
Clinton also had one of the highest approval ratings of any president since World War II, which stood at 60%. Since his presidential days, Clinton has devoted his days to writing his memoir and bringing to life a presidential library in Little Rock, Arkansas.
Jennifer Love Hewitt and Will Friedle
When Love Hewitt and Friedle were just 18 years old, they played best friends on the set of the movie "Trojan War" and kicked off a true love relationship from there on. Later on, Hewit would play one of Friedle's love interests in "Boy Meets World." The relationship between the two on set was far more interesting than what was going on in reality, and the couple split up not long after they became publicly known as an item.
Both Love Hewitt and Friedle were big names during the 1990s and were the future to make it big in the industry. "Boy Meets World" is what brought fame to Friedle, and "Pary of Five" is where Love Hewit became known to almost every household in the world.
Larisa Oleynik
Nickelodeon star Larisa Oleynik captured kids’ imaginations as a girl named Alex with superpowers on "The Secret World of Alex Mack." As a teen idol, she made American youngsters all over the world wonder how awesome it would be to be a famous TV star.
After graduating from high school, she went back to acting and landed roles in the cult classic "10 Things I Hate About You" and the hit show "3rd Rock from the Sun." But she wasn’t done with school. Oleynik finished off her education at Sarah Lawrence College in Yonkers, New York. She said it was the best decision she ever made.
David Copperfield and Claudia Schiffer
Some call it love, some call it magic, and some just call it being one of the most famous couples in the industry (back then). 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! However, the engagement would never bloom into a marriage. The pair split up in 1999.
What's particularly peculiar about the pairing is the controversy that surrounded it. Many have speculated that the relationship was a long ruse in order to boost Copperfield's fame. However, both Schiffer and Copperfield strongly deny this. Hmm...
Kelly Ripa and Mark Consuelos
Kelly Ripa and Mark Consuelos met in 1996 on the daytime soap opera "All My Children" as co-stars and love interests. (Not much acting necessary!) These two seem to have found the secret to being a successful couple in show business as their careers have not gotten in the way of their marriage of almost three decades.
As a family of five, the TV star couple has three children together and maintains a photogenic relationship. “We care about each other deeply,” said Kelly, “Relationships evolve, and we just happened to be lucky enough that we evolved together.” Mark agrees, “We really dig each other. I’m crazy about her,” he said, “We keep it going.”
Julia Roberts and Kiefer Sutherland
Both of these two had plenty of their own fame, though when this picture was taken, Julia Roberts's stardom was already in full swing. Kiefer Sutherland would need a little bit of time before “24” took off and took him with it. Still, here they are spotted together, playing a happy celebrity couple.
One thing we can't get over is the fact that Sutherland took the "whenever attending a party – bring something with you" rule a little too far. We can't ignore the six-pack of beer or a four-pack of fancy wine bottles he is holding in his hand.
Macaulay Culkin
Macaulay Culkin made his mark by outwitting thieves in his breakthrough role as Kevin McCallister in the box-office titans “Home Alone” and “Home Alone 2: Lost in New York.” The actor could not outwit his parents, who held conservatorship over his fortune and career. Culkin would become one of the first child celebrities to publicly “divorce” his parents and seek emancipation.
He would sadly spiral into addiction and a complete retreat from the public eye. The actor has made somewhat of a comeback in 2021's "American Horror Story: Double Feature," however, the Macaulay of the 21st century will never be able to relive the 1990s version of himself.
Neil Patrick Harris
Before Neil Patrick Harris landed his most prominent role as philanderer Barney Stinson in “How I Met Your Mother,” audiences knew him as “Doogie Howser, M.D.” Patrick Harris entered the world of acting at the young age of fifteen when he took on the role of the prodigal child doctor.
Patrick Harris’ multiple decades in front of the camera have earned him some impressive accolades and, even more impressively, no scandals at all! In 2015, he became the first openly gay man to present and host the Oscars. Patrick Harris is a doting father of twins with his husband, David Burtka.
Mel Gibson and Robyn Moore
When Mel Gibson and Robyn Moore met, he was an unknown actor, and she was a dental nurse, both living in New South Wales. They began dating, fell in love, and married in 1980. One year later, Gibson found international fame in the movie "Mad Max." The two were married for 26 years and had six sons and one daughter.
They separated in 2006 when it was revealed that Gibson was playing on the unfaithful side. This photo was taken in 1990 when the two were still happy together. The divorce was finalized in 2011, and Moore got one of the biggest divorce settlements in Hollywood history.
Drew Barrymore and Jeremy Thomas
In this photo, 19 years old Drew Barrymore married 32-year-old Jeremy Thomas, a Los Angeles bar owner originally from Wales. At the time of the wedding, the two had only known each other for six weeks. The couple was married only slightly longer than they dated. The couple filed for divorce only 39 days later.
Drew grew to become a Hollywood star. In the roaring 1990s, she was best known for her roles in "Never Been Kissed," "Ever After," and "Mad Love." Jeremy Thomas, on the other hand, remained Barrymor's first husband, with one of the shortest marriages in the industry.
Tommy Lee, Kelsey Grammer, George Clooney, and Jason Patric
You have to admit that one of these four guys draws the eye. That guy, middle-left, is Tommy Lee, the founding drummer for the heavy metal band Motley Crue. On the left side is actor Kelsey Grammer during his time as the title character in “Frasier.”
On the right is George Clooney – you might not have noticed since he doesn't have his almost trademark silver fox look yet (nor his Nespresso machine). Next to him is Jason Patric, an actor who has been in tons of movies but hasn't been in much in recent years. Not anything all that big, anyway.
Alyssa Milano and David Arquette
Alyssa Milano was under the age of 20 when she began her romantic stint with David Arquette. Those were the peak days of "Who's The Boss?" for Milano and the days of "The Outsiders" and "Parenthood" for Arquette. In this photo, the two are at the peaks of their careers, they ruled the red carpets of the 1990s, and they were an IT couple for a time.
There was such a buzz covering these two back in the day that you might have thought there was a huge love affair going on between them. The truth is, their story lasted for just over 60 days.
Bruce Willis and Sylvester Stallone
You might remember going to an amusement park for your birthday or some other kind of special event as a kid. This picture just proves that celebrities are big kids at heart. This picture of a few big Hollywood names was taken at Demi Moore's thirtieth birthday party at Six Flags Magic Mountain in Valencia.
Closest to us is actor Bruce Willis, and next to him is fellow action star Sylvester Stallone. On Stallone's other side is his then-partner, Danish actress and supermodel Brigitte Nelson. There's some guy to her left who looks a little shell-shocked if you ask us.
Robert Downey Jr.
It comes as a surprise to some people that Robert Downey Jr. was such a big name in the nineties. He was in plenty of movies and played well-regarded roles, but his off-screen antics made it hard for him to break into the A-list. Stints in and out of rehab cooled his star before the Marvel Cinematic Universe came calling.
This picture has a young RDJ leaving or entering Madonna's New Year's Eve Party on December 31st, 1991. It kinda looks like he's dressed as Charlie Chaplin — a flashy suit, a white scarf, and a bowler hat give him a unique look that really seems to work.
Madonna and Sean Penn
Sean Penn and Madonna met in the winter of 1985 and married soon after, in August of the same year. That's a good way to make one year the best in less than six months. "True Blue," one of Madonna's greatest albums, was, in fact, dedicated to Penn. In January 1989, just before celebrating their fourth anniversary, they decided to call it quits and got divorced.
Sean Penn and Madonna were, without a doubt, the pretty face of the early 1990s. She was just about to be crowned the Queen of Pop, and he already made some unerasable steps towards mega star success.
Ian Ziering
Who is this fabulously-dressed man, and when in the seventies was his picture taken? Well, he's Ian Ziering, best known as Steve Sanders on “Beverly Hills, 90210.” Of course, you probably know him as the voice of Vinnie on “Biker Mice from Mars.” And believe it or not, this picture was taken in 1992, just a few years after “Beverly Hills, 90210” hit television screens.
He's getting his groove on at the MTV Rock N' Jock Basketball Jam Benefit, but it doesn't look like anyone else is interested in dancing with him. We'll dance with you, Ian, even though to us, you will always be Steve.
Reese Witherspoon
She was young, she was beautiful, and she carried her cutlery everywhere she went. Some of those might still be true, but it's still fun to see Reese Witherspoon enjoying herself so much. After a lifetime of playing bubbly blondes, Witherspoon has done plenty of roles that have earned her plenty of awards, like an Academy Award, an Emmy, and two Golden Globes.
This picture might have been from before all that, but it doesn't look like she has a care in the world as she laughs against a backdrop of leaves. This pic is from 1996, at the premiere afterparty of “Freeway.”
Mariah Carey
Mariah Carey is known and loved all over the world for so many things. This photo was taken somewhere in the 1990s when the music scene was all electric with vibrant contras, and Carey was absolutely everywhere. Her greatest hits at the time were "Dreamlover," the Jackson Five cover of "I'll be There," and her number one holiday hit, "All I Want for Christmas is You."
And today, Well, today, Mariah Carey still sings, however, her vocals are not what they used to be due to vocal nodes. She will forever be the one singer who could sing five octaves and out-of-this-world whistle notes.
Halle Berry and Kevin Costner
There are a fair number of people hanging out in this picture, but which of them are names you would recognize? Well, one of them is easy – that's Halle Berry on the left. We're also told that Kevin Costner is present in this photo, and we're pretty sure he's the guy in the gray coat. Sitting next to Berry in the beret is her then-husband, baseballer David Justice.
This picture is from the grand opening of the Hard Rock Hotel & Casino in Las Vegas, which naturally attracted celebrities. There were cameras there, after all. Whether they were specially invited or had to get tickets normally, we'll never know.
Mary-Kate and Ashley Olsen
Mary-kate and Ashley Olsen are probably the most famous twins in Hollywood. In the 1990s, they rose to fame by starring as Michelle Tanner on "Full House," but behind the scenes, not everything was pretty pink. In a highly publicized interview with Marie Claire Magazine, Mary-Kate went so far as to characterize their stint as childhood stars as “little monkey performers.”
She explained that when she looks back, she doesn’t feel connected to the photos of herself. The twin said that they performed their act perfectly, but it was not a part of who she would become. Their fame as childhood actresses was phenomenal, and she’s happy to be rid of it.
Ted Danson and Whoopi Goldberg
This one is going to surprise you. While on the set of the 1993 film, "Made in America," Ted Danson and Whoopi Goldberg started a romance that has since been dubbed "the affair that cost Danson $30 million."
Ted Danson had been married to his wife, Casey Coates, for almost two decades when he and Whoopi ignited their romance. Once the secret was out, Coates filed for divorce, which ultimately cost Danson a cool $30 million as well as a butchered reputation. After a year and a half, Whoopi and Ted called it quits in an anything-but-amicable breakup. Was it all worth it?
Winona Ryder and Johnny Depp
The indie couple of the early 90s, Johnny Depp and Winona Ryder were the black sheep of Hollywood. Both dark-haired beauties that took on some quirky films, their love seemed like a match made in heaven. The two met in 1989 at the premiere of Ryder's film "Great Balls of Fire!" the classic biopic of the late Jerry Lee Lewis.
By the time they co-starred in "Edward Scissorhands" in 1990, the world was enamored by them. Constantly overwhelmed by the press, the public pressures weighed on their relationship. Eventually, they gave in and, by 1993, decided to go their separate ways.
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 Driver met on the set of the film and started dating. However, any goodwill 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! Damon is known for his remarkable roles in "The Informant" and "Saving Private Rian," and these days, for being Ben Afflecks best friend while Minnie Driver is hot on her podcast and publishing her memoir, "Managing Expectations."
Leonardo DiCaprio and Claire Danes
Who would have thought? Our "Homeland" queen holding hands with Jack from "Titanic" way back in 1996, before anyone knew what was waiting ahead for either of them. That same year, DiCaprio and Danes starred together in the 1996 edition of "Romeo and Juliet," which turned into a mega blockbuster.
At the time, there were rumors that the two were involved beyond their work in the movie, however, this was never confirmed by either side. For the premiere of their joint venture of "Romeo and Juliet," DiCaprio came hand in hand with Kristen Zang, who he dated for a while.
Going Down With a Smile
Courtney Love is known first and foremost as the widow of Nirvana's frontman, Kurt Kobain. Needless to say, Love before and after Kobain's passing had always been known for unbecoming red-carpet antics. Often showing up intoxicated and unloading on the press with profane language and behavior.
A scene such as this one at the 12th Annual MTV Video Music Awards, as awkward as it is, was so common that she wasn't even bothered and smiled on her way to the floor. In 2014 Love released two more solo singles and participated in a movie production. The last time we heard from her, she said she was working on new music.
Lori Loughlin and Billy Hufsey
Lori Loughlin was all about the limelight in 1990. She had one of the starring roles in “Full House,” which was one of the most popular shows on television at the time. While Loughlin's biggest role was that of Aunt Becky, she still has plenty of other well-known parts, like the main role on “When Calls the Heart.”
Here she is about ready to have some fun with a little bit of arm candy. His name is Billy Hufsey, and he had quite the list of credits of his own, including a famous poster he posed for in a towel and not much else.
Elton John and David Furnish
This dynamic duo met in 1993 at a dinner party hosted by Sir Elton John (yes, he was anointed the title by the late queen herself). Furnish, the Canadian producer — who also directed a 1997 documentary about Elton John — and Elton got engaged and entered a civil union in 2005.
Nine years later, in 2014, the same year that same-sex marriages were legalized in Britain, Elton and David got married. The two have also worked on various projects together, including 2011's "Gnomeo & Juliet." The Rocket Man himself and his life partner are publicly known for being one of the strongest couples in the industry.
Sandra Bullock and Matthew McConaughey
Sandra Bullock and Matthew McConaughey did a very good job of hiding their relationship, so 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.
Chloe Sevigny and Harmony Korine
Ah, young love! Before Chloe Sevigny was an acclaimed actress and Harmony Korine a cult-classic director, the pair were just friends in their early teens. When it came time to cast actors for his first film, "Kids," (1995) Korine turned to his long-time friend Sevigny. Once the film was completed in 1994, the pair became more than just friends and co-workers.
Sevigny and Korine embarked on an on-again-off-again relationship that lasted several years but finally ended in the early 2000s. However, the two remain close friends until this very day. Harmony Korine is a film director and a successful screenwriter.
Ian McKellen
Even before he became Gandalf the Gray and thrilled us with his magic, Ian McKellen was a fan of smoke rings, as this picture shows us. He's here seated with playwright Larry Kramer at the opening night of the Broadway play “Indiscretions.” Sure, it might not be a wild party – they're having drinks at the table, for Pete's sake – these aren't young men, not even in 1995.
That does make us wonder why this picture is in black and white if it wasn't all that long ago. We thought that this was taken in the sixties or something like that, but not even McKellen is that old.
Leonardo DiCaprio
Apparently, that's Leonardo DiCaprio, but it honestly doesn't look that much like him. In this pic, he's sneaking out the back of the film premiere for “The Beach,” which was a 2000 movie starring DiCaprio as an amoral backpacker looking for the perfect place to relax. It was an adaptation of a novel, but as is usual, the movie could hardly live up to the novel itself.
Leo rose to fame during the 1990s, unaware that he was about to become one of the most famous names in the industry and desired by so many. He was just 16 years old when he gave his first guest appearance, and from there, there was no return.
Mariska Hargitay
Mariska Hargitay is an actress, producer, and philanthropist, best known for her role as Olivia Benson in the ever-running television show "Law & Order". She has since starred in many movies and shows. Some of the most memorable moments on screen for her were in "Plain Truth," "Night Sins" and "Lake Placid."
In this photo, Mariska is seen in Beverly Hills when she attended the premiere of the 1993 movie, "Indecent Proposal." The movie was a huge hit at the time and became one of the most talked about movies of that era. Hargitay was an A-list star, appearing and galavanting in all mega-events.
Hugh Grant and Elizabeth Hurley
As costars do, Hugh Grant and Elizabeth Hurley met and fell in love on the set of the 1987 film "Remando al Viento." The couple was together for an impressive 13 years (which may as well be 50 years in Hollywood time). However, the relationship was far from perfect, and like most Hollywood relationships, a third party was involved, and we'll just say it wasn't on Hurley's side.
Hugh was caught in a rather compromising position with a... let's call her a lady of the night... in 1995. Despite the shock and hurt on Hurley's part, the two stayed together for another five years before finally ending their relationship.
Richard Gere and Cindy Crawford
In 1987, Richard Gere already had a resume of women he had dated, which listed, amongst others, Kim Basinger, Priscilla Presley, and a few other big names. Stunning Cindy Crawford was only in her early twenties when she met Mr. Gere, which led to the two marrying in 1991.
Crawford didn't want to waste her precious twenties with the silver fox and decided to untie the knot. She was one of the hottest women alive during the 1990s, and he was and still remains, a true charmer any woman would love to have. They were, without a doubt, the Brangelina of the 1990s.