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Captured: Rarely Seen Images Of Celebrities From The 1990s

Photo: Twitter.com/ddoniolvalcroze

The Cold War ended in 1991, and served as a signal of the dramatic cultural transformations to come around the world during that decade. People were excited for the new millennium, even if nobody knew how it would play out, especially with the Y2K chaos.

The following photos of celebrities throughout the 1990s show most stars had their own look and their own story to tell. These photos portray a time before the Internet connected everybody to everything at all times. These rarely seen photos of stars during the last decade before the new millennium will surely bring back feelings of nostalgia. There’s no better way to understand where these celebrities came from and learn new things about them, than by digging through the archives…

Anna Nicole Smith’s Odd Marriage

Photo: Reddit

In a highly scrutinized act, 26-year-old Anna Nicole Smith married 89-year-old J. Howard Marshall in 1994. Smith married the octogenarian billionaire one year before his death. The couple had met in 1991 while she was performing at a strip club in Houston, and they had a two-year affair where Marshall gave Smith lavish gifts while supposedly asking her to marry him multiple times. She finally agreed and the two were wed back in Houston.

It goes without saying that Marshall’s children weren’t happy about Smith getting a cut of the inheritance. At the time, Smith claimed that she and Marshall had an oral agreement that she would receive half of his estate, which was worth approximately $1.6 billion. Since it wasn’t stated in his will, it never came to fruition.

Mariah Carey & Will Smith

Photo: Mariah Carey

While today Mariah Carey and Will Smith are household names, in 1988, they were still trying to make names for themselves.This particular photo was taken at radio station KIIS-FM’s “Endless Summer Jam,” where Smith teamed with DJ Jazzy Jeff.

He performed lesser-known tracks like “Parents Just Don’t Understand” and “Nightmare on My Street.” Two years after the photo was snapped, Carey released her breakout self-titled album. Also, Smith starred on the show that launched him to stardom, The Fresh Prince of Bel-Air.

The Winona Ryder & Johnny Depp Romance

Photo: Reddit

Johnny Depp and Winona Ryder were one of the most famous Hollywood couples of the early 1990s, dating from 1989 through 1993 after meeting on the set of Edward Scissorhands. Although they were eight years apart in age, it didn’t matter to them. That is, until they wanted to get married.

John Waters, the director of Crybaby, was thrown into an awkward situation when Depp asked him to marry the two even though Ryder’s father refused to give his blessing since Ryder was only 19 years old. Waters later wrote that he managed to get them to call off the wedding before the attorneys did the paperwork to get him ordained as a minister.

From Standup To Acting

Photo: Reddit

Jim Carrey still hadn’t fully made it in Hollywood in the 1980s despite his clear talent for impersonations and physical comedy. He was a standout on In Living Color, but hadn’t latched on in the acting world yet.

Carrey struck gold with his role in Ace Ventura: Pet Detective. The film made $107.2 million. Later, other movies starring him like The Mask and Dumb and Dumber brought in over $700 million. Oddly enough, Carrey said that he didn’t get famous because he was funny or working hard. He said it was because he was desperate, which was a necessary part to learning or creating anything.

Jennifer Aniston & Brad Pitt

Photo: Hello Magazine

Jennifer Aniston and Brad Pitt at a Sting concert may be the most “1990s” thing ever, as they were two of the biggest stars of the 90s.  In 1999, they were in New York City celebrating their engagement when they attended the concert.

They dated for around one year prior to getting engaged, although they initially tried to keep the relationship a secret. Despite their efforts, Aniston and Pitt were caught together at the Tibetan Freedom Concert. There have been plenty of rumors of the two reuniting after Pitt’s divorce from Angelina Jolie. While it would make a lot of fans happy, it has yet to happen.

Leonardo DiCaprio’s Wild New Year’s Eve

Photo: Pinterest

Coming off the success of Titanic, What’s Eating Gilbert Grape and Romeo & Juliet, Leonardo DiCaprio was ready to let loose on New Year’s Eve 1998. He flew some friends down to Miami on a private jet and rented a mansion.

To ring in the new year, they went to party at Bash, a nightclub affiliated with Sean Penn. Allegedly, DiCaprio jumped onto a podium and started dancing provocatively for the crowd. People magazine later reported that he had dined on beluga caviar and smoked oysters that night. Bollinger champagne was his drink of choice, which went well with the occasion.

Ryan Gosling The Mormon

Photo: Vogue

Ryan Gosling has been a Hollywood heartthrob for a while now, having been thrust into the spotlight since the 1990s as a child actor. His early roles include being a member of The Mickey Mouse Club, acting on Goosebumps and portraying the young Hercules.

Most people don’t know that he was raised in a strict Mormon family, and while his mother is different now, she admits that he was raised by a “religious zealot.” At age 16, Gosling moved to Los Angeles, leaving his mother’s religious rule behind. He found a place in Skid Row so he could be close to reality and far away from the glamorous Beverly Hills.

Liv Tyler Finds Her Father

Photo: Reddit

Liv Tyler was one of the most famous celebrity kids of the 1990s, but she didn’t even know that Aerosmith’s Steven Tyler was her father until she was eight years old. She said she didn’t know who her dad was because her mother was a bit of a carefree spirit when she was younger, leading to some confusion about who her real father was.

Liv clarified that her mother was young when she had her, but she was loved and taken care of by everybody in her family as she grew up. She figured out who her father was because they had similar looks and Mia looked so much like her that they could’ve been twins.

Jennifer Lopez The Actress

Photo: Reddit

Another icon of the 1990s, Jennifer Lopez could sing, dance, and  act. To top it all off, she was beautiful and was beloved.While not originally an actor, Lopez made such a name for herself that she almost created the opportunity for herself.

While she appeared in several films prior to the 1998 debut of Out of Sight, it was that film that was arguably her greatest hit. However, she was upset with the initial offers for her services. She noted that her co-star, George Clooney, was getting a lot of money for the movie. The movie studio wasn’t offering her anywhere near a similar amount. She stood up for herself and was able to negotiate a much better dollar figure.

The One Where They Go To Vegas

Photo: Today.com

The popular sitcom, Friends followed six friends as they dealt with life and love in New York City. The director took the cast of Friends on a trip to Las Vegas in 1994 before the show premiered so they could bond more and told them once the show aired, everyone would know who they were.

Jennifer Aniston recalled the director saying that the cast needed to stick together and take care of each other. The director of the show handed each cast member some money and said, “Now go into the casino and go gamble because this is the last time you’ll be able to walk into a casino anonymously.” Sure enough, he was right.

Meghan Markle, Again

Photo: Vicki Conrad

Before she was British royalty, 16-year-old Markle attended a Christmas dance in 1997 with her high school boyfriend, Luis Segura. Markle went to Immaculate Heart, a girl’s catholic school in the Los Feliz neighborhood of Los Angeles. Her boyfriend at the time went to a boy’s school called St. Francis, located in La Cañada Flintridge.

A source who knew the high school couple said the two were quite the item. The source told The Daily Mail that Luis was madly in love with her. Markle was sweet to him and they were fun to be around.

Elon Musk In College

Photo: Reddit

Musk immigrated from South Africa to Canada as a teenager. He then worked several odd jobs before starting college at Queen’s University. His roommate was Navaid Farooq, a Canadian who grew up in Geneva. To make extra money while in school, Musk sold computer parts. He also helped fix the computers of his classmates, essentially starting a business while he was still a teenager.

Later, he explained that he could build something to suit their needs. For example, he created a tricked-out gaming machine and a simple word processor that both cost less than retail. Also, if their computer didn’t start properly or had a virus, he could fix it.

Edward Scissorhands Reminded Tim Burton of Someone

Photo: Reddit

Despite having droves of fans who love him for his acting and good looks, Johnny Depp has never been comfortable with himself as a star. Originally, he had moved to Los Angeles to become a musician, but transitioned into film because acting was easy for him. In an interview with Rolling Stone, he mentioned that he connected more with weird outsiders than he did with models and the upper class.

Director Tim Burton explained to the magazine why he was drawn to Depp for the role of Edward Scissorhands. He found similarities between the character of Edward and Depp, both people being perceived as something they were not, and that there was pain, humor, darkness, and light within both.

Forrest Gump & Nike

Photo: Paramount Pictures

Forrest Gump is likely at the top of most people’s lists for best films of the 90s. One of the many random things that the film did was reintroduce the Nike Cortez shoes to people who may not have even known about them.

These shoes were from the pre-Jordan era of Nike and had a classic look that went with most casual outfits. They also worked well for running, as Gump wore them to run across the country. While the Nike Cortez were available in many colors, the most popular version was the red, white and blue version after Tom Hanks sported them in the movie.

Winona Ryder The Criminal

Photo: CNN

In 2001, Ryder was arrested for shoplifting at a Saks Fifth Avenue in Beverly Hills after being accused of trying to steal over $5,000 worth of designer clothes and accessories. While she was acquitted on the felony charge of burglary, Ryder did end up with three years on probation, nearly 500 hours of community service and more than $10,000 in fines and restitution.

Additionally, she had to attend psychological and drug counseling. While speaking about the crimes years later, Ryder gave a mysterious explanation for her actions. She said she had just wanted to “stop,” and the aftermath of committing the crime enabled her to set her mind outside of Hollywood.

Troubling Times For Robert Downey, Jr.

Photo: Reddit

Today, it’s hard to imagine Robert Downey Jr. as anything other than Iron Man. In the 90s, however, his life was on the rocks, having multiple run-ins with the law in 1996. The last occurrence was when he let himself into one of his neighbor’s homes and fell asleep. Before that, he had faced felony counts of possession of cocaine and heroin. In addition to that, he also faced misdemeanor counts of having a concealed weapon in his vehicle and driving under the influence.

In 1999, when all was said and done, he received three years in prison for repeatedly violating probation. After approximately one year in a treatment facility and state prison, Downey Jr. was released when a judge ruled that his collective time in those facilities qualified him for early release. Thereafter, he turned his life around, and has been a Hollywood mainstay since.

Matthew McConaughey’s Absurd Arrest

Photo: Reddit

In 1999, Matthew McConaughey was arrested for playing the bongos naked, possession of marijuana and resisting arrest, which sounds like something straight out of a movie. At the time, McConaughey was in the process of truly making it big. From starting out acting in commercials and music videos, he had built his way up to leading roles in full-length features by the time of his arrest.

He was later asked if he felt bad about the arrest. McConaughey joked that he had no regrets about what he was doing at the time other than forgetting to close the window for his neighbors.

Ryan Reynolds’ First Gig

Photo: Groovy History

Today, Reynolds gets millions of dollars for each film, but in the 1990s, he was just another child actor looking for his big break. He also hung out with very cute puppies.

His first role was on the show Fifteen, which aired on Nickelodeon. Reynolds said the actors were paid only $150 per episode, but it still made him feel like the king of the world. He still had a paper route while on it, so he’d film the show, go home, and complete his paper route each day. Since he was a kid, he had no concept of what a lot of money was and thought he was living the dream.

Peter Dinklage The Punk Rocker

Photo: Twitter.com/ddoniolvalcroze

Before he was a highly-decorated actor winning Emmys for his portrayal of Tyrion Lannister on the critically-acclaimed hit Game Of Thrones, Peter Dinklage was the frontman for a punk band called Whizzy. Though there aren’t any recorded performances available for us to see, there are a lot of photos online.

Dinklage says that he “was pretty angry back then,” during his time in the band. It’s not clear what exact genre of music Whizzy fit into, but much like Dinklage, perhaps they couldn’t be fit into one box, and performed an eclectic mix of styles. There is a video on YouTube with 11 million views of Dinklage singing about the greatness of his character of Tyrion Lannister. Until footage emerges of Whizzy, this may be what we have to settle for.

Macaulay Culkin & His Dad

Photo: Reddit

Culkin became a household name after starring in Home Alone. It was one of the highest grossing films of all-time, and he became the first child actor to be paid $1 million.

After the success of Home Alone 2: Lost in New York, Culkin’s father and manager, Kit, became well known in Hollywood like his son. However, sources noted that Kit was an outcast among Hollywood executives as he tried to get creative control of his son’s films. It wasn’t long before his pride did him in. Richie Rich was a dud at the box office in 1994 and Kit lost the power he longed for.

A Presidential Scandal

Photo: Reddit

Monica Lewinsky sent shockwaves around the world when she revealed an affair with President Bill Clinton in 1998. She was only 22 years old at the time. The scandal took over the headlines and will always be linked to the Clinton presidency. The two admitted to nine sexual encounters over a two-year timeline, although Clinton initially denied any wrongdoing. However, the “blue dress,” as it came to be known, had a stain that matched his DNA.

Near the end of 1998, the House of Representatives voted to impeach Clinton on two of the four articles of impeachment. Time went on to publish an article that stated the political damage had burned out Washington.

The Discovery of Pamela Anderson

Photo: Reddit

She was discovered as a spectator at a BC Lions’ Canadian Football League game. The stadium’s scoreboard camera focused on her in the crowd. She was wearing a cutoff Labatt’s Beer T-shirt and got so much attention that Labatt hired her as a spokesmodel.The spotlight on Anderson inspired her to take a leap of faith and move to Los Angeles to pursue acting and modeling.

She eventually secured the role of the original “Tool Time girl” on Home Improvement before starring on Baywatch. As time passed, Anderson became more popular than the show itself. While she stayed on Baywatch for five seasons, she was no longer just an actress, she was a global phenomenon.

Princess Diana & The Revenge Dress

Photo: Pinterest

Princess Diana and Prince Charles were married on July 29, 1981, but rumors of his infidelity were a constant in the press over the years, and the two became estranged in 1991.On the night of the 1994 Vanity Fair party, the world sided with Diana when she made an appearance in an iconic dress.

It was later known as the “revenge dress” after Charles admitted on television that same night that he had cheated with Camilla Parker Bowels. The dress was made three years prior, but Diana never wore it, as she thought it was “too daring.” In fact, she planned on wearing a different outfit to the event, but made a last minute decision to switch to the dress.

Julia Roberts’ Armpits

Photo: Reddit

In April 1999, Roberts made waves in more ways than one when she inadvertently revealed armpit hair while waving to the crowd at the premiere of Notting Hill. While it wasn’t a big deal in the grand scheme of things, there were plenty of rumors as to why she did this.

One rumor was that Roberts grew out her armpit hair because her boyfriend at the time, Benjamin Bratt, had a fetish for it. Another idea was that Roberts was making a feminist statement at the premiere. Unfortunately, there was no real exciting reason as to why she went with the armpit hair. Roberts claimed that she didn’t think the sleeve length on her gown would be that short, so she thought nobody would notice.

Another Baywatch Actor

Photo: Reddit

Today, Jason Momoa is mainly known for his role on Game of Thrones and Aquaman. Surprisingly, his career almost came to a halt before it started because of being a lifeguard on Baywatch Hawaii.

Momoa remembers his start as an actor being crazy due to being a college-aged kid who got to run around shirtless and hang out with beautiful women. He admits the role nearly cost him his newfound career because casting directors labeled him as solely a hunky lifeguard.

When the show ended, Momoa used all the money he earned from the show to rock climb and also travel the world. Lucky for his fans, he returned from his time away and picked up where he left off.

The Young Kardashians

Photo: Reddit

The Kardashian family was one of the most “1990s families” there was. Kim and Kourtney sported some serious styles of that era. Rob rolled with the spiky haircut and wide collars.

Robert Kardashian, the father, was most famous for being OJ Simpson’s friend and representing him in the famous murder case. In 2003, he died of cancer, but Kim thinks he’s still with them in a way. She has stated that she believes her son, Psalm West, is a reincarnation of her father since they are both left-handed and share  other similar qualities.

Sarandon Still Going Strong

Photo: Susan Sarandon

This photo of Susan Sarandon comes from her trip to Cannes in 1978. She and co-star Brooke Shields were promoting Pretty Baby. While the photo itself wasn’t from the 1990’s, Sarandon still was a big part of that decade, too, starring in Thelma and Louise. That movie got her a ton of accolades and was coined as a feminist film, even though it wasn’t initially meant to be.

Sarandon noted that she and the film crew inadvertently poked into a sensitive topic for many older white males. The powerful female characters rubbed a lot of them the wrong way. It never occurred to Sarandon that it would upset people to have women characters like that.

Brand Loyal

Photo: Pinterest

Anderson had gone from beer model to one of the most recognized stars of the decade by the mid 1990s. In that short period of time, she went from the girl next door to one of the biggest sex symbols in the world. She seemed to be everywhere, from television to movies.

Nevertheless, she still agreed to appear in Playboy, the magazine that helped launch her career. By the time this photograph was taken, she had appeared in Playboy fourteen times already. When Playboy asked why Anderson initially moved to Los Angeles, she said that Hollywood people are dreamers, always grabbing for something big. Since she was a dreamer, too, she felt like she belonged there.

Dennis Rodman & Madonna’s Wild Relationship

Photo: Pinterest

One of the most unique couples of this decade was Rodman and Madonna. In the NBA, Rodman made a name for himself first by hustle and physicality, then later by personality. He was known for his crazy dyed hair, piercings, and tattoos. Some of his antics included leaving his team in the middle of the season to go let loose in Vegas and even partaking in professional wrestling.

They were both revolutionary forces in the the worlds of sports and pop-music. On top of that, they pushed sexual limits in both their professional and personal lives. In his autobiography, Rodman stated that Madonna offered him $20 million to get her pregnant. He went as far as to write that she had a private jet ready to fly him to her New York City home to make it happen.

One of Angelina Jolie’s Favorite Roles

Photo: Reddit

Angelina Jolie has acted in all types of roles in her career, but it was her work in the 1990s that many remember her by. A couple of her most important roles to this demographic were as Lisa in Girl, Interrupted and Kate Libby in Hackers.

She won an Oscar for her role in Girl, Interrupted, portraying a young woman confined to a sanitarium back in 1967. Jolie loved the role, stating that she truly thought her character was the only sane one in the entire film. She was almost upset when people said she was great at acting insane because she never thought the character was insane.

Matt Damon’s Controversial Claim on Oprah

Photo: Reddit

Matt Damon and Minnie Driver started dating after meeting on the set of Good Will Hunting. Their relationship lasted a year, but ended when Damon told Oprah in 1998 that he was single and didn’t have a girlfriend, though he and Driver were still together at that point.

Driver, while being interviewed by the LA Times after Damon’s announcement, said she found the whole ordeal very inappropriate. She also pointed out that he had declared his love for her on David Letterman a month before that.

Kurt Cobain’s Stomach Pain

Photo: Reddit

Cobain’s picture was taken around the time of the release of his album, Bleach, in 1989. Known to have chronic stomach issues, he said that the strawberry Quik drink was one of the few things that made him feel better.

According to Cobain, his stomach issues were so severe that he’d vomit and that it made him want to kill himself. He ended up using drugs to subdue the pain.He later revealed that after six years, he finally received medication for his stomach pains. However, he never got an actual diagnosis for the mysterious illness.

Adele & The Spice Girls

Photo: Reddit

While countless girls today adore her today, as a child, Adele was once one of those little girls idolizing other stars.The Spice Girls were huge when Adele was a kid.

From the posters behind her in the picture, she was clearly obsessed with them. She was able to see them as a kid and got nostalgic when she got to see them as an adult. In 2019, when seeing The Spice Girls perform at Wembley as an adult, Adele stated that she hadn’t seen them there in 21 years.

A New Kind of Rap

Photo: Reddit

Eminem came out of poverty-stricken Detroit and had a rough upbringing himself. He was the catalyst for a new kind of cartoonish and brash hip hop. In 1999, when “My Name Is” premiered on TRL, it turned the world of music upside down.

Initially, his violent music appealed to mostly angry young men, but he proved to be one of the best rappers ever with his rhymes and speed at which he could rap.  His dark music appealed to people in the smaller communities in the United States because they related to him. Eminem’s music wasn’t for everybody, but everybody knew who he was.

Salma Hayek’s Telenova

Photo: Reddit

American audiences weren’t aware of Hayek until the middle of the 1990s, but she was famous in Mexico since the 1988 telenovela Un Nuevo Amanecer. Teresa, another telenovela, added to her growing fame.

With no luck in Hollywood at the time, Hayek complained about the lack of work for Latin talent right when director Robert Rodriguez was watching. That coincidence helped her land roles in two big movies, From Dusk ‘Til Dawn and Desperado. She went on to appear in five more Rodriguez films and even became godmother to his children.

Drew Barrymore Emancipated

Photo: Reddit

Barrymore lived quite the rollercoaster in the early 1990s. She and her mother partied at Studio 54 together, she rarely went to school, and she already had alcohol and drug problems as a minor. She said that the only comfort she found was in acting, so she decided to emancipate herself at 14 years old in order to get more roles. She wrote in her book that she wasn’t employable at the time and wanted to start her life over.

Barrymore moved into a Westwood apartment and got a job at a coffeehouse, where she sometimes even had to clean toilets. She admitted that she wasn’t great at her job and felt like a loser, but it helped her build character and eventually break out on her own.

Kim Kardashian’s Graduation

Photo: Reddit

Before her family was full of multi-millionaires, Kim was more or less a regular girl in Los Angeles. Her dad was a big lawyer and her then-stepdad was an Olympian, but she was far from being the celebrity she is today.

Kim still had the desire for fame at a young age. She was filmed at her middle school graduation in 1994 talking about what she wanted people to remember about her when she made it big. She told the camera to remember the beautiful little girl being filmed that day for when she later became famous. Those in attendance will always have a great memory of a young and confident Kardashian.

The Cast of Clueless

Photo: Paramount

Surprisingly, the idea of Clueless got passed up by multiple studios. By the time it ended up with Paramount Pictures, Sherry Lansing, the head of the studio, had faith in the film.

She wasn’t the only one excited to start, as the entire cast and crew were also thrilled to create the film. According to Paul Rudd, who co-starred with Alicia Silverstone, they had an inkling of how big Clueless would be. He said that after the initial table read, the young actors all went to a place nearby for some food. Rudd remembered how cool they all thought it was to portray people their own age, especially in a John Hughes movie.

The Protest Of The Teletubbies

Photo: BBC

Teletubbies was one of the most unique early childhood shows there was in the 1990s. The weird, colorful creatures worshipped a baby in the sun. The company rented land in Warwickshire, England from a farmer who dug out a bowl-like dip in the land for the show. Ironically, another show that had previously filmed in the area nearly ruined it for the Teletubbies.

When the locals of Warwickshire heard about another show coming to take over their town, they were furious. Anne Wood, the series creator, wasn’t aware of the other show and was surprised by protests. She had to make every effort imaginable to keep the peace, including keeping the filming location a secret and hiring a security team to keep the media away.

Drew Barrymore’s Disgusting Apartment

Photo: Pinterest

This picture looks like things were great for a young Drew Barrymore, but as you may remember from earlier, they definitely weren’t. She emancipated herself from her mother at 14 years old, only to realize she had no idea how to be an adult.

Barrymore did her best, but definitely wasn’t quite ready for the harsh reality. In fact, she told The Guardian that her apartment was such a mess that you needed a hazmat suit to go inside, with fungus growing everywhere. The apartment was in a bad neighborhood and she was scared to go to sleep every night.

Tweenage Meghan Markle With Her Mom

Photo: Reddit

Before Markle became the Duchess of Sussex and one of the most recognized people in the world, she was just a girl growing up in a suburb of Los Angeles called View Park. It was also known as “Black Beverly Hills” due to the demographics.

She wrote a letter at age 11 to First Lady Hillary Clinton with a complaint about a tagline in a dish soap commercial. Markle disliked the line that “women all over America are fighting greasy pots and pans.” Her efforts helped change the word “women” in the tagline to “people.” Markle said that with that small change, she understood how important her actions were. She then dedicated her life to fighting for equality.

Blake Lively, The Spice Girl

Photo: Blake Lively

Like Adele, Blake Lively was also a huge Spice Girls fan and has been since a child. In 2018, a Twitter user revealed that she made a crazy discovery when looking back through her old pics. When this user attended a Spice Girls concert back when she was five years old, she had her picture taken with a girl who she thought was Emma Bunton, also known as Baby Spice.

It turns out that the girl she posed with wasn’t a Spice Girl at all, but Blake Lively. When the picture was brought to Lively’s attention, she confirmed it was her in her own post online. It’s better to be tricked into taking a photo with a celebrity by a future celebrity than just some random doppelgänger.

Jared Leto’s Questionable Kiss

Photo: Pinterest

Leto played Jordan Catalano on My So-Called Life. It’s weird that at 21 years old, he was making out with Claire Danes on the set when she was only 14 years old. According to Danes, the kissing was because Leto was teaching her how to make out for a scene in the film.

She explained the questionable acting lessons to Howard Stern later on, as that would never fly in this day and age. Supposedly the script listed a scene where it said “Angela kisses Jordan’s face.” Danes didn’t understand why it read like that and Leto had to try to teach her.

Glenn Close & Woody Harrelson Were A Couple

Photo: Pinterest

Glenn Close and Woody Harrelson formed a rarely known 1990s couple. Close was around 15 years older than Harrelson when they dated in 1991, which may be part of the reason why it didn’t last longer than 6 months.

The age difference may make some people uncomfortable, and their outfits in this photo may have the same effect, as the style, or lack thereof, raised eyebrows. It’s also worth noting that Harrelson had already met and dated his future wife prior to this fling with Close. He hired his future wife as his assistant in 1987, dated her once in 1990 and then went back to her down the road. They’re now married with three kids.

Cher’s Shocking Attire

Photo: Reddit

Cher’s career was in doubt after her and Sonny Bono split in the 1960s. Many thought she wouldn’t last without the other half of her act, but she continued to be highly successful throughout the next two decades.

The woman of many talents continued to dominate pop culture into the 1990s with “Love Hurts” and the tour that followed. She wore leather and chains costumes during her performances, which raised eyebrows. Bob Mackie designed the dominatrix outfit pictured on Cher. His outlandish fashion work has been seen on other stars like Joan Rivers, Tina Turner and Elton John.

Tom Hardy’s Sobriety

Photo: Reddit

Tom Hardy today is one of Hollywood’s biggest stars, with a great versatility in the range of characters he plays. He almost didn’t get the chance to become famous because of a drug and alcohol addiction he had as a teenager and early twenty-something. At one point, it took him 28 days in rehab before realizing he had a problem.

Hardy has said he was always in some sort of trouble when he was younger, but things got real when he woke up in a pool of his own blood and vomit in London in 2003. Thereafter, he entered rehab and built himself up as a changed man. He’s been sober since he was 23 years old.

David & Victoria Beckham

Photo: Pinterest

Before they became the Beckhams, David and Victoria (who was known as Posh Spice at the time) met at a charity soccer game in Manchester. Only one year later, they announced their plan to marry in a joint press conference.

Victoria went on to give birth to their first child mere months before the wedding. On the fourth of July in 1999, she and David tied the knot at a castle just outside of Dublin. They became known for their matching outfits and jet-set lifestyle. While the two don’t share too much about their lives, they’re still one of the best power couples out there.

Michael Jackson, Kevin Connolly & Leonardo DiCaprio

Photo: Pinterest

Michael Jackson wasn’t a regular part of Leonardo DiCaprio’s crew. However, he did invite these other stars back to Neverland Ranch to hang out. A lot of famous people like DiCaprio don’t speak about visiting Jackson. However, Connolly, who is known to have played Eric on Entourage, has been more open about his odd experience.

When he spoke with Andy Cohen about the weirdest thing he saw at Neverland Ranch, Connolly exclaimed, “Bubbles,” the famous monkey that Michael Jackson owned.

Salma Hayek Turned Down Selena

Photo: Reddit

Hayek wasn’t actually in Lethal Weapon 4, but that didn’t stop her from attending the premiere in 1998. She was one of the most sought-after actresses at that point in time.

An example of this was the producers of Selena wanting her to take the lead role that eventually went to Jennifer Lopez. Hayek wasn’t interested. She claimed that the producers offered her the role only a week or so after Selena died. They had already planned to make the movie that quickly. She thought it was pretty distasteful to do that.

The Mask Almost Had A Different Love Interest

Photo: Reddit

The role of Tina, Jim Carrey’s love interest in the hit movie, The Mask, could’ve gone to Anna Nicole Smith. That change in lead actress would’ve created quite the different movie. Smith didn’t respond to the material given to her, so director Chuck Russell crossed her off.

Russell was at a loss regarding who to fill the role with until he came across Cameron Diaz’s headshot. He later told Variety that Diaz hadn’t even acted in anything else yet. They brought her in and she was the perfect woman for the part in his opinion, but he had to do a lot of extra work to convince the producers.

Penélope Cruz Acted Alongside Her Future Husband

Photo: Pinterest

Originally from Spain, Penelope Cruz got her first taste of acting by performing in commercials and television shows for her family. She would later study ballet at Spain’s National Conservatory before moving across the world to New York City.

In 1992, the 18-year0old landed her first film role in Jamón Jamón. She starred alongside Javier Bardem, who she would later end up marrying The couple didn’t end up marrying until nearly two decades later. They don’t speak publicly about their early time on-screen with one another, but fans would definitely be open to hearing about it.

Bill & Ted

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The movies Bill & Ted’s Excellent Adventure and Bill & Ted’s Bogus Journey came out two years apart. Keanu Reeves starred in both and became a superstar within that short gap in time before starring in The Matrix in 1999.

Point Break helped bring Reeves’ career to new heights when he starred alongside Patrick Swayze. He also happened to be preparing for the upcoming Bram Stoker’s Dracula, as well as the thriller, Speed. While the second film for Bill & Ted didn’t meet expectations, it helped continue to develop a cult-like following over the years. In fact, a third film, Bill & Ted Face The Music was released in 2020.

Fit Brad Pitt

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Pitt had to be extremely disciplined to get into amazing shape for his role as Tyler Durden in Fight Club. He had to diet and work out heavily.  He kept to a strict diet, that was pretty boring and clean. Most of his meals included one or more of the following: brown rice, pasta, green veggies, oatmeal, chicken, and fish.

He needed a protein-packed diet to help him power through his workouts. His weekly routine included four days of weightlifting, two days of cardio and only one day of rest.

Matthew Perry & Courteney Cox

Photo: NBC

A lot of Friends fans were all about Ross and Rachel, but another great love story was that of Chandler and Monica. Matthew Perry and Courteney Cox had great chemistry in their portrayals of the couple.

It makes sense that rumors soared that they were dating in real life. Although they’ve reportedly never dated, they do post photos together on social media every now and then. In 2019, Cox posted a photo with Perry while they were out to lunch. She captioned that she couldn’t be any happier, which naturally got the rumor mill churning yet again.

Tara Reid The Original Party Girl

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Reid has had a rollercoaster career. After striking gold in the American Pie films, she went into full party mode, and became the first party girl of the era, before both Paris Hilton and Lindsay Lohan.

The paparazzi found it easy to catch her at her worst during that phase, and it clearly had a a negative influence on the roles she received moving forward in the film industry.At one point later on, Reid told Time that she realized how her actions in the 1990s affected her career. She also stated that she wasn’t a big partier anymore, but was still living life to the fullest.

One Last Dose of Pamela Anderson

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Pamela Anderson, pictured with David Charvet in 1993, could’ve been left out of Baywatch. When the show initially had auditions, Baywatch’s star and producer, David Hasselhoff, didn’t want to hire Anderson to be CJ Parker.

He thought that she would be bad publicity because she was in Playboy. Maybe even more so, Hasselhoff was worried that her appeal would upstage him. Obviously Hasselhoff’s opinion wasn’t considered by the other producers. Anderson got the role and became the main reason people watched Baywatch. He was overshadowed, but he likely didn’t mind the money that came as a result of all the views.

Johnny Depp & Penélope Cruz

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Johnny Depp and Penelope Cruz were quite memorable as a couple in Blow, which was about the cocaine trade in the 1970s and 1980s. Cruz later joked that when she initially came to the United States, she only knew two phrases in English and one of them was, “I want to work with Johnny Depp.” Cruz’s wish came true, but she found it difficult to work with him because of his sense of humor.

She told The Daily Mail that even though she knew Depp’s tricks, he could still crack her up, which didn’t bode well on set. She mentioned that one time the crew was stuck for two hours and couldn’t finish the scene because they couldn’t stop laughing.

Don’t Get On Jennifer Lopez’s Bad Side

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The late 1990s was a great time to be Jennifer Lopez. She had been the star of Selena and Anaconda, while also releasing On The 6, a multi-platinum album. Her rise to stardom was based on hard work, so she was stoked to call out the critics who didn’t think she would be an A-lister. Lopez let it be known that she had a list of journalists she wanted to call out in an interview.

She brought up how happy she was with how Selena turned out, but out of the many good reviews the movie got, there were some bad ones, too.  Those negative reviews, and those who wrote them, were the ones Lopez remembered most.

Jessica Alba’s Classic Look

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Years before Jessica Alba was a big-name actress and makeup influencer, she was like some other teen stars in the 1990s. Similar to Ryan Reynolds, she was on Nickelodeon at one point, securing a minor part in The Secret World of Alex Mack. Idle Hands premiered five years later, which put her on the map as a beautiful young actress.

While Alba made appearances on various shows and films during her youth, she also modeled for Limited Too. In fact, she and Jessica Biel appeared in a spread for the clothing company.