Groovy Photos That Reveal A Different Side To The '90s

Can you imagine what it’s like to lose your anonymity in the blink of an eye? That’s exactly what happened to the cast of Friends when their show premiered on September 22, 1994 on NBC. The series followed six friends as they faced complex issues of life and love in New York City. The cast were all plucked out of obscurity to star in the series, but now they’re some of the most famous faces on the planet.

Before the show premiered they were taken on a trip to Las Vegas by the show’s director as a last hurrah before they faced the scrutiny of the public eye. Series director Jimmy Burrows took them to the city of sin for an evening of pre-fame dinner and gambling, but he also wanted to make sure they knew what they were in for. Jennifer Aniston recalled:

[Burrows said] ‘This world can be pretty dark, and you guys gotta really stick together and take care of each other.’And we took that to heart for sure, obviously. And then he handed us each a couple hundred bucks 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.’ And we had no clue what he was talking about… and sure enough, that was the last time we were able [to do that].

There’s no way that Markle had any idea she’d one day be sharing rarified air with the Queen of England, especially while attending a Christmas dance with her high school sweetheart, Luis Segura.

In the mid ‘90s Markle attended Immaculate Heart, an all girl’s catholic school in the Los Feliz neighborhood of Los Angeles while her high school beau went to all-boys St. Francis in La Cañada Flintridge. A source who knew the high school couple says that at the time the two were quite the item. The Daily Mail reports:

Luis and Meghan were very into each during their time as high school sweethearts. It's fair to say Luis was madly in love with her. And she was very sweet to him, fun to be around and loved his family too, so the memories are good.

After immigrating to Canada from South Africa a teenage Elon Musk worked a series of odd jobs before starting college at Queen’s University. By his own admission he knew nothing of his surroundings yet he still managed to get paired up with Navaid Farooq, a Canadian who grew up in Geneva, as his advisor on all things Canadian.

In order to make extra money, Musk sold computer parts and helped fix the computers of his school mates, essentially going into business for himself when he was still a teenager. He explained:

I could build something to suit their needs like a tricked-out gaming machine or a simple word processor that cost less than what they could get in a store. Or if their computer didn't boot properly or had a virus, I'd fix it. I could pretty much solve any problem.

No young star had lived quite as hard as Drew Barrymore in the early ‘90s. She and her mother partied at Studio 54 together, she barely went to school, and she was a teetering into drug and alcohol addiction before she could drive. Barrymore says that at the time the only solace she found was in work, so much so that she emancipate herself at the age of 14 so she could get more roles. She wrote:

I was never unprofessional, but I was on a hiatus from being employable. And when I turned 14 and wanted to start my life over, I wanted to do things on my own terms. On the day of my hearing, my mother was there in full support of my emancipation, which would mean me living on my own. I felt so sad, but too much had happened.

After moving out of her mother’s home Barrymore moved into an apartment in Westwood and got a job at a coffeehouse. She admits that she wasn’t great at her job and that at that point in time she felt like a loser.

It’s crazy to think that there was a point in time that Jim Carrey wasn’t famous. However, throughout the ‘80s and even when this collection of impersonations was put together he was doing whatever he could to make it Hollywood. At the time he was a standout on In Living Color, but by 1994 the personal check for $10 million that he wrote himself for “acting services rendered” was available to be cashed.

In ’94 Carrey changed comedy forever with his insane, rubber faced, over the top act. That February Ace Ventura: Pet Detective made $107.2 million, and later that year his films The Mask and Dumb and Dumber piled up a massive $706.1 million. Carrey says that he didn’t get famous because he was so funny or because he was working so hard, but because he was desperate. He told 60 Minutes:

Desperation is a necessary ingredient to learning anything, or creating anything. Period. If you ain’t desperate at some point, you ain’t interesting.

Angelina Jolie has captured the hearts and imaginations of viewers throughout her career, but it’s her work in the ‘90s that’s most beloved by millennials. Two of her most important roles (at least to ‘90s kids) are her turn as Kate Libby in 1995’s Hackers, a movie that’s extremely cheese but has a cult following to rival Rocky Horror Picture Show, and as Lisa in Girl Interrupted.

Jolie won an Oscar for the role that saw her acting out as a young woman confined to a sanitarium in 1967, and she says that she still holds the character close to her heart. She stated:

I really, genuinely thought I was the only character who was sane in the entire film. And if you watch it closely, that's exactly how I was playing it: I am just the only sane person here. I was actually almost upset when people said I was so good at playing insane because I never thought she was insane. She was just incredibly honest, which, I guess, made her seem crazy.

It’s so strange to see the voice of a generation in such a vulnerable relationship, crouched on the floor and drinking strawberry Quik. According to Cobain his stomach pains were so bad that he’d vomit from the pain and that it made him want to kill himself.

Cobain said that strawberry Quik drink was one of the few things that could actually sooth his stomach, at least in the very early ‘90s. He ended up using drugs to medicate his pain, and even though he visited multiple doctors he never had a reason behind his stomach problems.

He revealed that after six years he finally received medication for his stomach issues but he never got an actual diagnosis for the illness.

Is there anything more ‘90s than Brad Pitt and Jennifer Aniston hanging out at a Sting concert? These two were in New York City in November 1999 to celebrate their engagement. The two even going the famous bassist/singer/tantric sex guy on stage to sing a bit of “Fill ‘Er Up.”

The two were dating for about a year before that although they went through huge pains to keep their relationship a secret - even though they were caught hanging out together at the Tibetan Freedom Concert.

There were few couples from the ‘90s who could capture the hearts of fans the same way as Brad and Jean, is it any wonder that people are still hoping they’ll get back together?

Coming out of the a poverty stricken Detroit Eminem was the catalyst for a new kind of over the top, cartoonish and brash hip hop that changed the world. When “My Name Is” premiered on Total Request Live in 1999 it turned the world of pop upside down.

At first, Eminem’s soap opera lyrics and violent musical leanings simply appealed to angry young men, but he proved to be one of the best verse men alive. He provided insight into the “other” America, a world let down by societal decay.

The darkness in his music appealed to people from middle America because they could understand where he was coming from. Even though he was consummate class clown there was something in his early music that moved the nation.

Sure, we had the internet in the late ‘90s but it wasn’t the internet that we have now, it was a nicer place where a star could just pop off and not get in trouble or get torn apart on Twitter. As a matter of fact there was no Twitter. The ‘90s were seriously awesome.

J. Lo proved the awesomeness of the under the radar ‘90s in a post Selena interview where she dropped dime on Oliver Stone’s sex life, talked up her acting abilities, and said that she deserved more money for her work in Out of Sight. She said:

I think George Clooney’s getting $10 million for this movie. [Universal] thought they were going to get me cheap from the beginning, but I kept telling my agent, ‘No, no, no! Keep asking!’ When my agent called me saying, ‘What should we say to them?’ I said, ‘Say, who’s going to break their ass to promote this movie while George is on ER? Say, Anaconda is now over $100 million worldwide and why do you think girls between 18 and 25 went to see it more than any other action movies–because of Ice Cube?

In 1998, Matthew McConaughey was just a high school senior who was trying to figure out what to do with the rest of his life. He was voted "Most Handsome" which is a pretty exciting win for a teenager, but even though he was destined to become one of our most beloved actors he was more concerned with being a football player, or even a lawyer.

After high school McConaughey attended the University of Austin where he briefly studied law before switching things up to get his Bachelor of Science in Radio-Television-Film. It wasn't long after his graduation that he made his onscreen debut in the beloved Dazed and Confused.

Even though American audiences came to know Salma Hayek in the mid ‘90s she was a star in Mexico from the moment she appeared onscreen on the 1988 telenovela Un nuevo amanecer, her follow up Teresa, made her a household name thanks to its sultry mix of Dallas style soapiness and rags to riches storytelling. Without any luck in Hollywood, she complained about the lack of work in Hollywood for Latin talent just when up and coming director Robert Rodriguez happened to be watching.

This fortuitous even placed her in two of the coolest movies of the ‘90s, From Dusk ’Til Dawn and Desperado, the follow up to Rodriguez’s indie hit El Mariachi. She appeared in five more of Rodriguez’s films and become godmother to his children.

Hayek took the success that she made for herself in the ‘90s and turned that into award gold while creating diversity in an industry in which there was none.

It’s hard to imagine a time before these two superstars were, well… superstars. Both Carey and Smith are two of the most famous people in the world today, but in 1988 they were still working their way up the entertainment ladder.

This photo was taken at KIIS-FM's "Endless Summer Jam,” where Smith was performing with DJ Jazzy Jeff. The Los Angeles Times wrote that Smith “won over the crowd with such paeans to teen Angst as the hit "Parents Just Don't Understand," and with its current hip-hop tribute to slasher flicks, "Nightmare on My Street.”

Two years later Carey released her breakout self titled album and Smith appeared on the brand new Fresh Prince of Bel-Air.

It feels crazy to think that in 1995 there were people who doubted the success of Clueless, that there were executives who passed on this decade defining film. By the time the project ended up at Paramount Pictures the film had been around the horn a couple of times, but head of the studio Sherry Lansing had faith.

She wasn’t the only one. The entire cast and crew had a blast making this film and according to Paul Rudd (who co-stars alongside Alicia Silverstone) they had an inkling of how important the film would be. He explained:

After the table read we all went and got a bite to eat. We went to a place not far, around the corner, that I used to go to, which was kind of a bar. They probably should not have let some of those kids in. I do remember all of us sitting around saying, ‘How cool is it that we’re all going to do a movie about kids our own age?’ And having that conversation about the John Hughes movies to our generation. It had been a while since there was one of [those]— How cool would it be if this thing had legs? 

It’s as if Ryan Reynolds and his boyish good looks have been around forever… or at least since the ‘90s. Today he commands millions of dollars per film and has his own gin company, but in the ‘90s he was just another actor looking for his big break.

His first role was on the show Fifteen which aired on Nickelodeon, if you remember this series let us know because… uh… we’ve never heard of it. Reynolds didn’t make a lot of money for the role but he says it still made him feel like a million (or gajillion) bucks:

I remember we were paid 150 bucks per episode. And I still had a paper route so I would do my TV show and then I’d go home and do my paper route each day. For me, I thought I was, like, a gajillionaire. For $150 a day, it was like a dream come true.

Whether you watched the Teletubbies or not you were definitely aware of this weird furry creatures with giant bellies who worshipped a baby in the sun. The series didn’t come form outer space (even if it felt like it) but rural England.

The BBC children’s series rented land in Warwickshire from a farmer who excavated a bowl-like dip for the crew, but another show that had filmed in the area nearly ruined the whole thing for the ‘Tubbies. When Warwickshire locals heard about a new show coming to their village they were up in arms. Series creator Anne Wood remembers:

I hadn't realized that another TV show had been filmed in the area and had caused havoc, so the locals started protesting about us. I had to make my case to the planning authorities, wondering how, if they refused me, I'd explain to the BBC that I'd spend £150,000 digging a hole and might have to spend another £150,000 filling it in. I assured them it was a low-key children's program and no one would be aware of the filming. But as soon as it was broadcast, we had photographers crawling across fields and hovering from helicopters. We had to hire a security firm to police the site. We were so keen to keep the location a secret, we would blindfold visitors.

This picture paints a sunny disposition for a young Drew Barrymore, but her life at the time this photo was taken was anything but bright. She emancipated herself from her mother at the age of 14 only to realize that she didn’t know how to be an adult.

Barrymore did her best, but who knows how to take care of themselves when they’re just a teenager? Certainly not this young party girl. She told The Guardian that her apartment was such a mess that you needed a HAZMAT suit to enter:

I had no idea how to run an apartment at 14. There was fungus growing everywhere, it was a disaster. It was in a dangerous neighborhood and I was so scared to sleep. I had bars on the window and alley cats f*cking 30 feet away. I was so terrified.

This photo proves that even stars can be fans. In 2018 twitter user @briarmadrid went to her first Spice Girls concert when she was only five years old and had her picture taken with a girl she thought was Emma Bunton, aka Baby Spice.

When that twitter user found the photo later in life she realized that the girl she posed with wasn’t a Spice Girl, but Blake Lively.

That has to be quite the shock, realizing that you were in contact with a future celebrity at such a young age. When the picture was brought to Lively’s attention she posted it online and wrote, “Pretending to be someone else... since 1997… Sorry -not sorry- I tricked you into thinking I was [Baby Spice].”

Look, we all had a crush on Jordan Catalano, the hottie who couldn’t read on one season wonder My So-Called Life, but it’s still a little weird that a 21 year old Jared Leto made out with a 14 year old Claire Danes on the set.

According to Danes the smooching was on the up and up because Leto was teaching her how to make out for a scene that they were filming (that old trick). She explained the “acting lessons” to Howard Stern:

There were these stage directions in that scene where it says ‘Angela kisses Jordan’s face,’ and I was like, ‘What? What is that about? Why would she kiss his face?'I had that question on set, and he had to try to teach me. It’s ridiculous!

There's no way that would happen on set today.

There’s a lot going on in this photo that’s hard to comprehend when it’s all being shoved in your face like this. First off, the clothes. We know that the weird puffy sweater was a thing in the ‘90s but what’s up with the landscape design? Maybe it just looks weird on Woody Harrelson.

Now Glenn, what’s happening with your hat? We love you, you’re the best Cruella DeVille that ever was but this is not the fashion statement to make when you have such gorgeous hair.

Finally, who knew that these two were dating? They don’t really make sense together but we like it. Hopefully they’re still friends.

In spite of his heart throb looks Johnny Depp has never been at ease with himself as a movie star. He moved to Los Angeles to become a rock ’n roll guitarist but found his way into film because acting was easy.

While filming Edward Scissorhands, Rolling Stone profiled the actor and found that he was more at home with weirdo dreamers than he was with models and the glitterati. Director Tim Burton told the magazine why he was so drawn to Depp:

Like Edward, Johnny really is perceived as something he is not. Before we met, I’d certainly read about him as the Difficult Heartthrob. But you look at him and you get a feeling. There is a lot of pain and humor and darkness and light. I think for him [the role] is probably very personal. It’s just a very strong internal feeling of loneliness.

Forrest Gump is filled achievement both technological and whimsical, but one of the best things that the film did was reintroduce the Nike Cortez to viewers may not have even known about it.

These shoes from the pre-Jordan era of Nike have a classic look to them that look good with any jeans that you want to throw on, or if you’re actually going to run cross country like Mr. Gump they’ll work for that too.

The Nike Cortez came in a variety of colors, but the most classic version is the red white blue version that became iconic when Tom Hanks held them up to camera for the whole world to see.

Cher’s career was supposed to be finished after she and Sonny Bono split in the ‘60s. Audiences who weren’t hip to her campy, over the top performances didn’t think that she had legs without her duo gimmick, but she continued to rise above the naysayers throughout the ‘70s and ‘80s.

The singer/actress/amazing talkshow guest continued to dominate pop culture in the ‘90s with “Love Hurts” and the following tour where she wore BDSM inspired costumes throughout her lengthy set.

The dominatrix outfit pictured was designed by Bob Mackie, a designer whose work has been seen on Joan Rivers, Ru Paul, and pretty much any diva who wanted to get weird.

Tom Hardy is one of the most immediately captivating actors of the 21st century, with transformative roles across genres he’s the kind of person who you never want to stop watching when he’s screen.

He almost didn’t get the big screen stardom that he hungered for thanks to an intense addiction to drugs and alcohol.

Hardy says that while he was always in a bit of trouble as a young man, things became real in 2003 when he woke up in a pool of his own blood and vomit at the Soho in London. He entered rehab and found sobriety to be freeing, allowing him to become the man he is today.

It’s interesting to think that one of the most beloved couples of the millennial generation got together in such a short period of time. David and Victoria met at a charity football match in Manchester where sparks flew. A year later and they announced their plan to marry in a joint press conference - can you imagine that happening today?

Victoria gave birth to their first child a few months before they tied the knot, and on July 4, 1999 (what a date) the two were wed at Luttrellstown Castle near Dublin. The two quickly became known for their matching outfits and jet set lifestyle.

While the two are quiet about their lifestyle, at least we know that to be Victoria’s lover David was able to get with her friends.

Is there anything more ‘90s than these three guys just hanging out? While Jackson wasn’t a part of DiCaprio’s… ahem, posse, he did invite up and coming stars back to Neverland Ranch to hang out.

Big stars like Leonardo DiCaprio haven’t spoken about visiting Jackson, but people on the periphery, like Connolly, have been more open about their strange experiences. When asked what the weirdest thing he saw at Neverland Ranch, Connolly told Andy Cohen:

The craziest thing I saw when I visited Neverland Ranch was Bubbles. I played with Bubbles… There was lots of weirdness but that’s another show in itself.

‘90s hottie Salma Hayek wasn’t in Lethal Weapon 4 but that didn’t stop her from strutting her stuff at the premiere. She was one of the most wanted actresses at the time, but that didn’t mean that she felt like she had to take whatever roles were thrown at her.

She says that the producers of Selena desperately wanted her to be the star of Selena but she wasn’t interested in playing the part because she thought it was distasteful. She explained what happened to Andy Cohen:

[The producers] offered it to me like a week after she [Selena Quintanilla-Perez] died. It was a little bit distasteful. They were already planning on making this movie.

It seems insane that Cameron Diaz wasn’t immediately given the role of Jim Carrey’s love interest Tina in The Mask the moment that producers saw her, but before awarding her the role they decided to try out Anna Nicole Smith. That definitely would have been a very different movie.

Smith didn’t respond to the material at all so director Chuck Russell passed on her. He didn’t know who to fill the role with until he found Diaz’s headshot. He told Variety:

I saw Cameron’s 8x10 on the casting desk and asked, ‘What about her?, I was told she was submitted but had not acted in anything else yet. I said to bring her in and let’s see... [She] was the only person for the part as far as I was concerned after her first reading. And then I saw the chemistry with her and Jim. Eight callbacks later, including improvs with Jim, I finally convinced producers.

Hailing from Madrid, Spain, Penelope Cruz got her start similarly to other young actresses when she performed commercials and television shows for her family. She went on to study ballet at Spain’s National Conservatory before moving to New York City.

Cruz was hired for her first film role in 1992’s Jamón Jamón where she starred alongside Javier Bardem - her future husband.

It’s fascinating to think that these two were acting along side one another when they’d marry nearly two decades later. The couple haven’t spoken about their early time with one another on screen, but it must be something they think about.

Liv Tyler is possibly one of the most famous celebrity children of the ‘90s but she didn’t even know that Steven Tyler from Aerosmith was her father until she was eight years old.

Tyler says that she didn’t know about her famous dad because her mother was a bit of a carefree spirit when she was younger which lead to some confusion about her real father. However, when she saw her half sister Mia she realized that she was a member of royalty. She told Jonathan Ross:

My mother was very young when she had me and there was a little bit of confusion about where I came from but I was very loved and very well taken care of by all my family, which was wonderful… I kind of figured it out because he looked exactly like me and I have a sister named Mia who is a year younger than me and I saw her standing at the side of the stage at a concert and I was literally like looking at my twin.

The difference between Keanu Reeves of Bill & Ted’s Excellent Adventure and Bill & Ted’s Bogus Journey is only two years, but in that time Reeves became a downright superstar. He was in Point Break at the same time as this film was released and getting prepped for Bram Stoker’s Dracula and Speed.

Even in this photo you can see that Reeves is a star, he looks like he’s about to be a centerfold for a teen magazine. The film wouldn’t meet the expectations of the original movie, but its developed a cult following in the decades since its release. So much so that a third film in the series is set to be released in the 2020s.

Anyone who’s seen Fight Club, be they man, woman, or meathead, has wondered how Brad Pitt got in such amazing shape for his role as Tyler Durden. He’s basically one giant ab shoved into a pair of Levis. It’s equally impressive and mystifying.

In order to get into god-like shape Pitt had to maintain clean and conscious eating habits that had him noshing on fish, chicken, veggies, and lot of protein.

To maintain his five to six percent body fat he was eating nearly constantly and four days of targeted weightlifting exercises along with two days of extreme cardio, and a day of rest.

Friends fans were head over heels for Ross and Rachel, but the real love story was between Chandler Bing and Monica Geller. Matthew Perry and Courtney Cox have amazing chemistry on the show, so it’s no surprise that rumors flared that they were secretly dating during filming.

The two have reportedly never had a thing, but they continually stop the flames of fan anticipation by posing in photos with one another on social media from time to time. In 2019 Cox posted a photo with Perry alongside the caption, “Guess who I had lunch with today....I KNOW!! Could I BE any happier?”

Tara Reid has seen her share of ups and downs in her career. After hitting it big in the American Pie films she went full party girl and became the paparazzi’s favorite celebutante, something that may have had a negative influence on the roles she received.

While speaking with Time Magazine during the filming of Sharknado 2, Reid says that she realizes how her actions in the ‘90s affected her negative, but that she’s not a party girl anymore. She said:

You feel like you’re in jail. You’re not going to get the parts. You’re trying to be on your best behavior and no one respects it. So you might as well just travel the world, meet new people, have fun. I can get hit by a bus, or fall on ice and die. At least I can say I’ve lived a really full life.

It’s crazy to think about it now but before Baywatch premiered the show’s star and producer, David Hasselhoff, didn’t want to hire Pamela Anderson as C.J. Parker. Not only did he think that she would be bad for the show because she was in Playboy, but she was worried that her bodacious bod would upstage him.

Clearly Hasselhoff was overruled by his other producers or he came to his senses because Anderson was hired and she became THE reason people watched his show about sexy lifeguards. Even though Hasselhoff was overshadowed he must have loved the cash that came in from all those viewers.

Johnny Depp and Penelope Cruz definitely cut a striking figure as a couple in Blow, a film about the cocaine trade of the ‘70s and ‘80s. According to Cruz this was the culmination of her life up until this point. She jokes that when she came to America she only know two phrases in English and one of them was “I want to work with Johnny Depp.”

She got what she wanted (twice) but she found that it was hard to work with the actor because of his strange sense of humor. She told the Daily Mail:

The only problem is he has a very peculiar sense of humor – and even though I know all his tricks, he can still crack me up. I can’t stop laughing when we are working so we had a few problems on the set. One time we were stuck for two hours and couldn’t finish the scene because we couldn’t stop laughing.

In 1999 Jennifer Lopez was at the top of her game. She’d gone from “flygirl” on the set of In Living Color to star of Selena and the smash hit Anaconda, not to mention her multi-platinum album.

Her rise was predicated on a ton of hard work on Lopez’s part and she was more than happy to call out the critics who didn’t think she had the stuff to be on the A-list. In an interview at the time she admitted that she had a list of journalists that she wanted to hang out to dry:

There are certain people that are marked for death already… Like, I was totally happy, totally confident with my work in Selena, but out of the 700 reviews–and I read every single one–I can quote the one who said, ‘The one thing you don’t do when you walk out of this movie is say, ‘Who’s that girl?’ I was like, ‘You lying b*tch!’

Long before she was a major makeup influencer and actress Jessica Alba was like a lot of teens stars in the ‘90s. She was on Nickelodeon and she popped up on various shows here and there, but she also did some modeling for mail catalogue stalwart the Limited Too.

When she was in her early teens Alba and another Jessica (Biel) appeared in a modeling spread for the cool clothing boutique.

In the magazine she’s engulfed in the oversized sweatshirts and turtlenecks of the day, she definitely embodies this classic ‘90s look that millennial remember from the hallways of their junior high.