Rarely Seen Photos That Reveal A Different Side To The 90s
By Sophia Maddox | August 11, 2023
Will Smith smeared with cake at the 'Fresh Prince Of Bel Air' wrap party
The following unseen photos from the 90s are definitely too hot for some viewers. Are they for mature audiences only? We’ll leave that decision up to you…
The final decade of the millennium was an era of change. Generation X had taken the societal reigns from the Baby Boomers and letting their hair down. Fashion was taking a turn for the flannel, and young people were beginning to look for new ways to have a good time.
These snapshots of the 90s show that the decade was full of a kaleidoscopic mix of culture, fashion, and music that made it an unforgettable era to live in - when Anna Nicole Smith was a legitimate celebrity and when Johnny Depp was still considered an independent film star.
It’s important to use these pictures from the 90s to take your preconceived notions of the decade and turn them on their head. That’s the coolest part about taking a deep dive into the past… you never know what you’ll find on the other side.
Every kid growing up in the ‘90s remembers watching The Fresh Prince of Bel-Air, Will Smith’s first foray into acting. It was fun, cool, and dare we say… fresh. The show made Smith a household name but according to the star the only reason he accepted the role was because he was in trouble with the IRS.
Following the breakout hit “Parents Just Don’t Understand" Smith ended up blowing through all of his money and with a huge IRS bill. When the duo’s second album flopped he was in deep trouble.
After hanging out around the Arsenio Hall Show for a while he bumped into none other than Quincy Jones. The two started hanging out and they spitballed the entire concept of Fresh Prince. They pitched the series to Brandon Tartikoff of NBC in Jones’ driveway and the show ran from 1990 to 1996.
Alicia Silverstone on the set of ‘Clueless’, 1995
At the naive age of 19 Alicia Silverstone stepped into the spotlight as Cher Horowitz in Clueless, a film that unwittingly set the template for teen movies throughout the ‘90s. From the look, to the dialogue, and even the fact that it’s a loose adaptation of a Victorian era novel (Jane Austen’s Emma), Clueless created a template for everything that followed.
Even though the film is considered a ‘90s classic, during production the studio heads were unsure if the film was going to be a hit or if it was going to Audi 5000 out of the theaters.
The film was a success, but Silverstone says that the way she was spoken about in the media made her feel “extremely isolated” from her peers, but that she learned from the toxic landscape around her and came out better for having lived through it.
The face that launched a thousand ships... Julia Roberts, early 90s
Hands down there was no bigger star in the ‘90s that Julia Roberts. Maybe Arnold Schwarzenegger but that’s arguable. Her big break came in 1990’s Pretty Woman where she played a sex worker who teaches Richard Gere about love and life but she almost didn’t star in the picture.
Three days after she was cast in Pretty Woman (originally titled 3,000) the production company backing the film folded. After Disney picked the film up and brought on Garry Marshall he agreed to meet with her as a courtesy, although he planned to cast a Hollywood A-lister in the role. Roberts explains the rest:
This small movie company folded over the weekend, and by Monday, I didn’t have a job. Garry Marshall came on, and because he’s a great human being, he felt it would only be fair to meet me, since I had this job for three days and lost it. They changed the whole thing and it became more something that is in my wheelhouse.
Is there a more star crossed/‘90s/extremely chaotic love affair than that of Tommy Lee and Pamela Anderson? After meeting in February 1995 they decided to get married after four days of courtship. They just took off to Cancun and got married on the beach… Anderson wore a bikini and Tommy Lee wore board shorts.
Call them trashy, call them over the top, call them whatever you want but Pam and Tommy were absolutely iconic. It’s impossible to think about the mid ‘90s without remembering that they were all over TV and the late night commercials promoting their sex tape.
After three crazy years and a couple of kids the two called it quits following an assault by Tommy Lee. He served four months after pleading no contest and in spite of their divorce they continued to see each other off and on for the next decade.
The truth is out there... Gillian Anderson from 'The X-Files' shows some skin
In the early ‘90s no show ignited the fervor of the fan boys quite like The X-Files. Every Sunday night on Fox from 1993 to 2002 Mulder and Sculley solved some of the weirdest cases involving aliens, bigfoots, and the government… that is until Mulder mysteriously disappeared and left Scully with a new agent in the final season.
During the show’s initial run no one was hotter than Gillian Anderson as Dana Scully, a by the books scientist thrust into the world of the unknown. Even when she was in scrubs or power suits there was something about her that drove fans gaga.
She was a legit sex symbol throughout the decade (and frankly still is), but this semi-gothic photo shoot with Anderson baring more than usual must have made her fans freak out when they saw it.
Sandra Bullock gets a piece of Ben Affleck
Promoting a film must be awful. You’ve got to go around and answer the same ten questions and try to make your answers sound like they’re totally off the cuff. Unless you have the right co-star then you’re going to be bored by the time you’re half way through the tour cycle.
Thankfully for Ben Affleck he was promoting Forces of Nature with Sandra Bullock. Something about her just seems fun and like she’s down for anything. She clearly doesn’t mind a little PDA on set. Even though it looks like it’s all fun and games with these two in 1999 Bullock told Entertainment Weekly that there’s one thing she can’t stand about him:
Ben can never show up anywhere on time. When he’s with you he gives you so much attention you feel like a queen, so when he says ‘I’ll call you for dinner’ and you don’t hear from him, you feel like, ‘What did I do wrong?’ Since he does it to everyone, you can’t take it personally. But then if you don’t call him back right away when he calls, he goes nuts, leaving messages like, ‘Why didn’t you call me back, I called you an hour ago, why don’t you call me BACK?’
Sarah Jessica Parker is stunning post work out
Sarah Jessica Parker has been on our screens and in our homes since the ‘80s, but it was in the last decade of the millennium that we really got to know her. Sure, she was great in LA Story and Sex and the City, but her outfits were really one of her greatest contributions to society.
Parker was known just as well for her drop dead sexy looks on the red carpet as well as the simple and cool outfits that she wore on the streets of New York City.
Just look at the way that she makes this workout gear look like haute couture. If only we looked this good while we were working out…
Hugh Grant, photographed by the LAPD in 1995
In 1995 Hugh Grant was on top of the world. He was dating Elizabeth Hurley, one of the sexiest women in the world and his career was taking off. Hot off the success of Four Weddings and a Funeral he was knee deep in the promotion cycle for four different films when he was caught on a side street in Los Angeles being pleasured by a sex worker named Divine Brown in his car.
Both Grant and Brown pleaded no contest and he was fined $1,180 before receiving two years probation and an order to complete and AIDS education program. Brown received a similar sentence but also received 180 days in prison.
When Grant appeared on The Tonight Show with Jay Leno to promote the film Nine Months Leno asked him “What were you thinking?” To which Grant replied, “I think you know in life what's a good thing to do and what's a bad thing, and I did a bad thing. And there you have it."
They could be twins... Kim and Kourtney Kardashian, 1994
The Kardashians have been in the public eye for what feels like eternity but in the ‘90s they were just another family living in Los Angeles. Sure, their father was a hot shot attorney and their then step-father was an Olympian but they were about as regular as could be in Los Angeles.
Kim and Kourtney have always loved the camera and this photo shows it. If you look at the family’s photos from the ‘90s it’s clear that they totally nail the fashion of the era from dark lipstick to thin eyebrows and even Jncos.
Many people have commented that Kim and Kourtney looked like twins growing up and that’s because they were born only a year and a half apart. No wonder they’re so close.
There’s no doubt that Jawbreaker exists because of the popularity of teen movies in the late ‘90s, but this sexy, thrilling film is an entirely different beast than films like Can’t Hardly Wait or 10 Things I Hate About You.
With a small budget (only $3 million) the cast and crew operated with no oversight from the studio which allowed the filmmakers to create a decadent, nasty little film. McGowan said of the production:
There was nobody telling us we went too far. We had a feeling back then that it was kind of the Wild West; Darren created this environment in which we could just be our wicked, delicious selves, and what came out of it was something that can’t be replicated.
For a brief period of time in the early ‘90s Vanilla Ice was something of a magnet for starlets. Somehow, with his single hit, “Ice Ice Baby” he was able to ensnare pop goddess Madonna in a relationship. However, he broke things off when she started working on her photography book “Sex.” Ice explained:
She was older than me and a great lover. But I broke up with her after she printed that book because I was hurt to be an unwitting part of this... package. It was disgusting and cheap. We were in a relationship yet it looked like she was screwing all these other people.
Released to coincide with her fifth studio album, “Erotica,” “Sex” featured gorgeous and elaborate photos taken by Steven Meisel and Fabien Baron of Harper’s Bazaar. The book was a smash, selling out its limited 1.5 million run in only a few days. The book is still one of the most in demand out of print books and Vanilla Ice is… well, we don’t actually know what he’s up to.
This Canadian beauty is best known for her time on Baywatch and her *ahem* private home video with former husband Tommy Lee, but it was hard to look anywhere in the ‘90s without seeing at least a fleeting glance of Pamela Anderson.
After being discovered at a Canadian Football League game when the camera panned in on her she was quickly offered her first Playboy shoot… she just had to figure out how to get to America. Anderson was stopped from flying to America because she didn’t have a work permit, she was told that if she didn’t have the proper paperwork she couldn’t enter America so she left the airport and went to the bus station and headed to Seattle. She explains:
They didn’t check me at the border, so I got into America. And I did my first Playboy cover.
Whether you were a sports fan or not, life in the ‘90s was dominated by one team - the Chicago Bulls. With six championship wins between 1991 and 1998 there was no way anyone walked through this era without knowing that Michael Jordan and his teammates were giants among men in the NBA.
As the defacto team leader Michael Jordan was the person that everyone on the team looked to for guidance, but that didn’t mean that they were best friends. Rodman was the best rebounder in the game in the ‘90s, but even though he was on the team with easily the best player in the league he says that the two men never spoke outside of practice. In 2019 Rodman explained:
We never talked to each other. The only time we talked to each other was probably on the court. Off the court, we never talked to each other.
Joaquin Phoenix grew uncomfortable with his photoshoot so he started doing dishes, 1996
Joaquin Phoenix has never been someone who feels comfortable with his fame. Following the death of his brother River in 1993 he retreated from the spotlight and essentially gave up acting for a while. He didn’t step in front of a camera for another two years when he appeared in Gus Van Zan’t’s To Die For.
Interviews with Phoenix are notoriously strange. He’ll either go inside himself or become combative with the interviewer, and every once in a while he’ll do something completely off the wall… like doing the dishes at a local restaurant. Photographer George Holz explained how he got this fascinating shot:
We were shooting at the funky Bell Café in Soho. Joaquin had this nervous energy — I had a lot of set ups in mind, but realized right away he wasn’t the kind to sit still for a photograph, so I threw all my ideas to the wind and totally shifted gears. I abandoned all my pre-lit set-ups and we wandered around the Café. We talked a lot—the conversation ranged from vegan cuisine to the paparazzi and his late brother River. He went into the kitchen and there were all these dirty dishes stacked up. He said: ‘Man, these need a wash!’ and put on an apron and just started scrubbing.
Its feels like Paris Hilton has always been in the media spotlight. She jumped to fame as a model when she was only 18 with a photo spread in Vanity Fair put together by David LaChapelle and went on to star in The Simple Life with friend and fellow socialite Nicole Richie, but there’s not much known about her early life.
By all accounts she led a strange life, or at least strange to people who aren’t the children of hoteliers. At the age of 13 she was living in Los Angeles where her bedroom was a suite in the Waldorf-Astoria Hotel in Beverly Hills.
Her friends were Ivanka Trump and Kim Kardashian (of course) and according to the young socialite whenever Michael Jackson performed in the area she was invited.
Justin Timberlake and Ryan Gosling, 1994
It’s crazy to think that two of the biggest stars in the world - Justin Timberlake and Ryan Gosling - got their start on the Disney Channel’s The All New Mickey Mouse Club. During their time on the show in the ‘90s they showed off their singing and acting chops.
While speaking about his time on the show with Ellen DeGeneres, Gosling noted about how inadequate he felt when he watched Britney Spears and Christina Aguilera perform:
I remember when we first got to the show, they sort of had all the kids perform for one another. I remember it was Christina Aguilera and then Britney performed and I remember thinking, 'Oh, OK, so they're like freakishly talented.' I was used to working with talented people, but that was another level.
Jennifer Aniston looking angry and hot for Rolling Stone, 1999
Even though her father was a soap opera actor she wasn’t exactly a pampered child. Her parents divorced when she was young and she looks to this moment as the thing that defined her life going forward.
While speaking with Rolling Stone in 1999 she noted that even though she has very few friends in Los Angeles they’re the people she knew before she was famous and that’s how she likes it. She explained:
This, I know, comes from having a divorced family, watching emotions run rampant and trying to understand them. But I credit my friends. I never got with a bad crowd. When I moved to L.A., I didn’t go through the wrong people to find the right ones. I have the same group around me that I’ve had since I landed here ten years ago. The most important thing is to stay focused.
Tom Cruise and Nicole Kidman photographed by Herb Ritts in 1999, they divorced two years later
In 1999 Tom Cruise and Nicole Kidman were finally finished with the psychotic filming process of Stanley Kubrick’s Eyes Wide Shut. After more than a decade of being the most beloved couple in Hollywood they were fraying at the ends - although they didn’t want anyone to know it.
Prior to filming Kubrick put together a three person therapy session where he psychoanalyzed Tom and Nicole’s marriage in order to blur the lines between fantasy and reality, something that they weren’t excited about, but who would be? Kidman explained:
Tom would hear things that he didn’t want to hear. It wasn’t like therapy, because you didn’t have anyone to say, ‘And how do you feel about that?’ It was honest, and brutally honest at times.
The couple survived the lengthy shoot but not for much longer. By February 2001 they were officially separated and they divorced that summer. Rumors abounded out the reasons surrounding their break up, but it's hard to imagine that spending a year in therapy with Stanley Kubrick in England didn't play a part in it.
Babyfaces - Tobey Maguire and Leonardo Dicaprio go bowling
Leonardo DiCaprio and Tobey Maguire met when they were 12 years old at an audition in the late ‘80s, likely for one of the many family sitcoms that were on the air at the time. Rather than become rivals the two formed a bond that’s lasted throughout their careers.
In the ‘90s these two became the focal point of young Hollywood, starring in huge films and getting into some good old fashioned antics. According to Dicaprio, Maguire is one of the most important people in his life. He explained:
Every single choice I’ve made I’m talked to Tobey about, and vice versa. we’ve had endless conversations about certain projects and argued with one another and supported one another along the way.
Kurt Cobain in New York, January 1992. A the time he was already thinking of breaking up Nirvana
It wasn’t easy to be Kurt Cobain. Following the release of Nirvana’s sea change of an album, “Nevermind,” he wasn’t just one of the most famous people on the planet - he was the voice of a generation. A year after the album’s release he was struggling with fame and an attempt to kick heroin, which wasn’t helped by the press constantly attacking his his wife, Courtney Love.
In 1992 a Vanity Fair article detailing Love’s ongoing use of heroin while she was pregnant. In response Cobain wrote a letter to DGC owner David Geffen threatening to break up the band is something wasn’t done about the remarks. He wrote in part:
This article has outright accused my wife of all kinds of hideously vile things to the point where Ive never seen such a crucifixion in a magazine. The woman's entire objective was to harm Courtney and now after you read the article (I hope) something may be done about it… I am now in rehab going on 18 days and Im really looking forward to having a family at this point [eff] NIRVANA… We are capable of displaying a healthy attitude before our audience and the next record is easily as good as the last one, but I'm so extremely [upset] about this piece of trash journalism that I'll lay anything on the line for the love of my wife and daughter.
Geffen responded to say that articles like this come and go and that he should focus on his music and his family, not on the journalism surrounding his work.
A breathtaking photo of Angelina Jolie taken in 1998
In the early ‘90s Angelina Jolie was essentially a cult star. A beautiful young actress with enticing eyes and a million dollar smile, she played tough chicks in b-movies and a hot hacker in her first blockbuster role, but it was her starring role in Gia that earned her a Golden Globe and established her as a star to watch.
Following her win for Gia she was profiled in People Magazine and photographed by the great Greg Holzer. He later said that during the shoot Angelina was captivating and exciting, that she was down for anything:
Angelina arrived with no makeup, no publicist, and no entourage, and settled in with my glam squad. She was incredible in front of the camera. We did the safer images that the magazine required in the beginning, then ended up shooting for hours more. Inventive, spontaneous, and fearless, she gave 100% to the camera… Angelina was the perfect combination of model and actress: beautiful and very self-aware, yet emotionally rich and expressive. When people ask, ‘What was your favorite shoot?’ I always think of this one.
In the makeup chair with Tim Curry during production of It, 1990.
‘90s kids were absolutely terrified at the start of the decade when Tim Curry put on the face paint to play Pennywise the Clown in ABC’s miniseries adaptation of Stephen King’s It. The two-part, four hour miniseries wasn’t just freaky, it also introduced an entire generation of young people to the devilish delights of Curry.
There were a lot of great actors and off the wall performers considered to play Pennywise (Roddy McDowall, Alice Cooper and Malcolm McDowell were just some of the names tossed around) but it was Curry who was chosen thanks to his horrifying take on a clown. He explained:
I just let it happen. Clowns are your worst fear realized. I think I scared a lot of children.
A young James and Dave Franco playing Super Nintendo in the early 90s
Growing up in Palo Alto, California as the sons of a mother who worked as a children’s book author and a father who worked in telecommunications but was actually a kind of mad math scientist the Franco brothers were infused with the restless creative spirit of their parents.
James and his brother Dave lived like normal young people. They played Nintendo, they got into small trouble, and they witnessed their father carry out science experiments in their backyard. What? Your dad didn’t do that? James told Rolling Stone:
He had this theory that there was gold running through the rivers, and if he figured out how to collect it, he could put it together. He never figured it out, but I remember all these little Tupperware buckets of river water in our backyard, with strainers in them, and they were his experiments.
Princess Diana having a dip in the sea while on holiday on Nevis Island in 1993.
The first chance Diana had to go on vacation following her split from Prince Charles she fled to Nevis, the oldest British colony in the Caribbean. The island is fairly untouched by civilization with its wild donkeys, goats, and pristine waters.
While on the island Diana stayed at the 19-room Montpelier Plantation & Beach, exactly the kind of place you want to stay after breaking things off with your royal family.
The island is still the perfect place to find solitude. There are no cruise ships or long haul flights near the island, which means the beaches are as secluded as you need them to be, and if you’re a former princess you need them to be very secluded.
Dennis Rodman gives David Letterman matching green hair on the Late Show, August 1996
After Dennis Rodman joined the Chicago Bulls at the start of the 95 - 96 season he was no longer just the bad boy from the Pistons but a member of a full blown championship team.
Rodman started appearing on Letterman’s show in video segments whenever the smarmy host was in town. In 1996 Rodman appeared as a guest on the actual show and brought along some spray on hair dye that he used to color Letterman’s fairly boring hair-do.
This was one of the many segments during the ‘90s on Letterman’s show that would become polarizing, along with Drew Barrymore’s birthday dance and Madonna’s many many f-bombs.
Young Ashton Kutcher lost the title of Male Model of the Year in 1998
One of the most memorable faces of the late ‘90s is Ashton Kutcher, and while most of us know him as Kelso from That ‘70s Show he began his career as a male model. When he was discovered at The Airliner bar in Iowa City, Iowa he was selling plasma to pay his college tuition and readily accepted the call to use his face to make some cash.
After winning the "Fresh Faces of Iowa" modeling competition Kutcher dropped out of school and moved to New York City where he snared commercials for Calvin Klein and modeled in Paris and Milan.
He went on to appear in a series of Abercrombie & Fitch campaigns before popping back over to Iowa and moving to Los Angeles - all in a span of two years.
Brooke Shields with her longtime pal Michael Jackson
These two stars may seem like an unlikely pair, but the similarities surrounding their rise to fame are uncanny. Both child stars who went onto fame as an adult, both stars uniquely understood the cost of becoming a sensation at a young age. After meeting in 1978 the two young celebrities immediately became close. Shields explained:
We had a bond... both of us needed to be adults very early. It was the most natural and easiest of friendships... Michael always knew he could count on me to support him or be his date and that we would have fun no matter where we were.
In 1993 rumors circulated that the two were dating, and Shields later said that Jackson had asked her to marry him multiple times but she always turned him down. In 2001 Jackson explained the magical circumstances under which he met Brooke Shields:
She was one of the loves of my life... her pictures were all over my wall, my mirror, everything. and I went to the Academy Awards and this girl walks up to me and says ‘Hi, I'm Brooke Shields.' Then she goes, ‘Are you going to the after-party?' I go, 'yeah.' ‘Good, I'll see you at the party.' I'm going, 'oh my god, does she know she's all over my room?' so we go to the after-party. She comes up to me she goes, 'will you dance with me?' I went, 'yes. I will dance with you.' man, we exchanged numbers and I was up all night, singing, spinning around my room, just so happy. It was great.
Cindy Crawford for Vogue November, Monaco, 1991
Helmut Newton is known for taking evocative and stirring photos in stark black and white. Drawing from erotica and high fashion, his work is often daring and always has the allure of something extremely sensual.
When it comes to photographing a model Newton says that he doesn’t like to tell them too much, he just needs them to get it. He explained what it’s like to photograph Cindy Crawford, one of the most beautiful women on the planet:
The woman in the image can be mysterious and to me I think it’s important that she is mysterious. So even in the way a woman walks down the staircase like Cindy walks down, I like the way that the legs open. I like the muscles that I see, I like the way the knees open. She walks down in a certain way. Well, I show the girl what I mean and if she’s smart, she gets it immediately.
Reese Withershpoon backstage at a Counting Crows concert in 1996
Audiences have been welcoming Reese Witherspoon into their homes since 1991 when she played Dani Trans in The Man in the Moon, but she wouldn’t become a breakout star until 1996 with the thriller Fear.
Following the release of what was meant to be a Mark Wahlberg vehicle Witherspoon starred in some of the most beloved films of the late ‘90s. But at the time this photo was taken she was just a young woman enjoying a night at a seriously ‘90s concert - the Counting Crows were jamming the on “Recovering the Satellites,” which meant Witherspoon definitely sang along to “Long December.” Photographer Randall Slavin explained how he snapped this adorable pic:
We were backstage at the Wiltern after a Counting Crows concert when I took this picture of Reese Witherspoon and another young actor, Eddie Mills. They were hanging out a bit, and Eddie and I were friends. This was right after Fear came out — 1996 was sort of her breakout year.
Johnny Depp admitted to Playboy that fans sent him extremely weird gifts
In 1996 Johnny Depp was at a strange place in his career. Both revered for his off-beat acting choices and looked at as a heart throb, he was trying to figure out the next stage of his career all the while under the focus of the public eye.
While speaking with Playboy that year Depp discussed the strangest things that his fans sent him in the mail (from “primitive” personal photography to pubic hair) to the way he feels about his famous looks. When asked how he felt about being so handsome that women send him strange gifts he responded:
I have no control over that. It's demeaning when people talk about my looks. I think I usually look [terrible], and most people would probably agree.
Amy Winehouse with her mother Janis, 1998
Amy Winehouse is one of those stars who shined brightly before burning out only a few years after becoming one of the biggest stars in music. Her whisky and cigarette soaked vocals brought danger back to pop radio, but her addictions got the best of her and she passed away on July 23, 2011.
As a teenager in the 1990s Winehouse attended the Sylvia Young Theatre School in London where she worked out of her vocals and her songwriting skills. At the same time she was also getting into trouble, acting out in ways that were only a preview for what was to come. Her mother wrote of the young woman:
Amy came into my life like a whirlwind and changed it forever. Although I lived through it with her, sometimes her story does not feel real. I am a proud mother who watched her daughter achieve the success and recognition she desperately wanted… She, herself, walked an endlessly unsteady tightrope between withdrawing from the limelight and needing to be noticed.
A teenager's bedroom in 1999... look familiar?
If you’re not experiencing nostalgia overload with this shot of a teenager’s room in the ’90s then you’re either not looking hard enough or you slept through the decade. Where do you even start with this guy’s room? It’s got to be the posters, right?
Teenagers have been obsessed with pop culture since that was a thing, but it wasn’t until the ‘end of the 20th century that there were so many different types of culture to become interested in A young person could love Buffy, South Park, and Friends, even if it was just an obsession with their stars.
The ‘90s was the first decade when it was no big deal to have your own TV, and these miniature numbers were a mainstay in bedrooms across the country… if you had a Playstation hooked up to your TV you were basically god in your friend group. What do you think happened to all that stuff? Is it in the trash or stored in an attic somewhere?
Backstage at a Versace show with Emma Sjoberg, Tricia Helfer & Veronica Webb 1994
There have always been models, those leggy angular women who are more like goddesses than regular humans but in the ‘90s the era of the supermodel began giving rise to runway stars like Naomi Campbell, Cindy Crawford, and Christy Turlington.
This influx of supermodels can be traced back to Gianni Versace, a designer who cemented their status with his Fall 1991 show that made use of these supermodels, specifically he models who appeared in the George Michael video for “Freedom.” At the end of the show the women strutted down the cat walk lip synching the song.
Versace’s “Freedom” moment showed that fashion could be used to affect pop culture in more ways than showing people what to wear.
Claudia Schiffer by Ellen von Unwerth guess campaign 1991
It’s hard to imagine now, but in the early ‘90s no one was quite sure who Claudia Schiffer was. Sure, she was a super hot model, but she wasn’t a super model until she was photographed by Ellen Von Unwerth. Schiffer’s raw talent was captured by Unwerth for this Guess campaign that’s both sexy and stylish.
Unwerth had a way about her that allowed her to help her models put their guards down when the camera was up. She knew that by making models feel empowered she could get the sexiest image of them. She told Harper’s Bazaar:
The women in my pictures are always strong, even if they are also sexy. My women always look self-assured. I try to make them look as beautiful as they can because every woman wants to feel beautiful, sexy and powerful. That’s what I try to do.
Fresh face Courteney Cox before her days on Friends
Born in Birmingham, Alabama, Cox began her career with a burst of rock ’n roll lightning when she appeared in Bruce Springsteen’s video for “Dancing In The Dark.” Two years later she took on the role of Alex P. Keaton’s girlfriend on Family Ties.
This was great and all, but throughout the late ‘80s and early ‘90s she was floundering in Hollywood with roles as girlfriends, but her big break came when she was cast in the NBC sitcom Friends as… Rachel? Cox was brought in to audition for the role of Rachel Green but realized she was wrong for the part. She convinced the producers to let her audition for Monica and the rest is history. She later explained:
For some reason, I thought I related more to Monica, which maybe it’s because I do. I’m very similar to her…I’m not as clean as Monica, but I am neat. And I’m not as competitive, even though some people, my partner Johnny McDaid, would say I am.
Danny DeVito gets a touch up for a scene in 'Batman: Returns,' 1992
During the filming of Batman Returns Danny DeVito had to deal with some seriously demanding co-stars. Much of his time on set was spent with literal penguins and not actors like Michelle Pfeiffer or Michael Keaton.
Aside from having to sit in makeup for hours and deliver psychotic dialogue he was stuck on a frozen wasteland of a set. Decades after the film’s release he explained the predicament to the Hollywood Reporter:
I'm the kind of guy that loves being on set, but it was cold... because we had real penguins and they had to keep the water really cold. They had these massive air conditioners. I was the only one really comfortable, because I had pounds and pounds of face prosthetics and the body padding, not to mention the heavy coat.
Lenny Kravitz, Lisa Bonet and Zoë Kravitz family portrait in 1989
This gorgeous family was only legally together for six years, with Lenny Kravitz and Lisa Bonet marrying in 1987 and bringing their daughter Zoë Kravitz into the world only one year later. The couple divorced in 1993 but Kravitz and Bonet have managed to stay friends and co-parents. Kravtiz told Essence:
You go through a marriage with somebody, you break up and it’s very difficult. But [Lisa and I] put the work in and we took the time so that we could become best friends again.
Today, Kravitz is close friends with Lisa Bonet and her husband, another ‘90s hunk, Jason Momoa. She said of their blended family, “It’s full-on family love.”
Gal Gadot visits the U.S. for the first time as a teenager in New York, 1999
Born in Petah Tikva, Israel, Gal Gadot had her yes set on studying law and international relations, although the modeling world was calling to her from a young age.
After visiting New York City in the ‘90s and before serving in the Israeli Army for two years she took part in the Miss Israel contest and at age 18 she did what no one expected - she won. Gadot explains that she was totally shocked when her name was announced:
I was 18, I just graduated high school and I had some time in between going to the army. My mom figured, 'Hey, why don't I send your photo, you finished school and this like a proper pageant,' whatever. I got in and I never thought I would win and then I won and then it scared me. I was like, 'What? Miss Israel? All the responsibility of being Miss Israel?'
Drew Barrymore ignoring the no shoes, no shirt, no service rules
Even though she first became famous in the ‘80s it’s the ‘90s when Drew Barrymore really came into her own. By 1990 Barrymore had an autobiography, she was living on her own, and she was about to start her second decade as a star after bouncing back from a tough beginning to her teens.
Always the paragon of fashion, Barrymore knew how to make any piece of clothing work - even when she was barely wearing any. The ‘90s were just as weird for the young actress as her hectic ‘80s. In 1994 she married a 31 year old bartender after only knowing him for a couple of months. Two months later they divorced.
Without any major acting roles to speak of around this time she posed in Playboy, to which her godfather Steven Spielberg responded by giving her a quilt for her 20th birthday with a note that read, "Cover yourself up."
Blue but not sad, Gwen Stefani on the red carpet at the MTV Music Video Awards, 1998
She have sang that she was “just a girl” but in the ‘90s Gwen Stefani was a fashion inspiration to an entire generation of fans.
Stefani didn’t shy away from her sex appeal but she definitely kept things weird and when it came to putting together a look for the red carpet. The first thing you’re drawn to in this shot from the 1998 MTV Video Music Awards (the best place to see a truly out there outfit) is the blue hair, how could it be anything else?
But what about that baby-blue furry bikini top, the platform sandals or the hovering futuristic skirt over pants? If you don’t have a look for Halloween you do now.
Born in Worcestershire, England in 1994, Styles grew up in a village of about 5,000 people that’s been described as “picturesque” but “quite boring.” Much of his early home life was easy, he hung out with his big sister and played on the empty hills surrounding his town but when his parents divorced when he was seven he was dealt an unexpected emotional blow.
Even with the emotional weight of his parents splitting up sitting on his young shoulders he still found time to be creative. He performed in school plays and listened to classic rock like Elvis and the Beatles. He even got into recording at a young age by using a karaoke machine that was given to him by his grandfather as a makeshift two track.
It’s clear that even as a boy Harry Styles was preparing himself for super stardom.
Johnny Depp and Winona Ryder at the 'Mermaids' premiere, December 1990
After meeting at the premiere of Great Balls of Fire! in 1989 Johnny Depp and Winona Ryder quickly became an item even though she was only 17 years old and he was 26 at the time. Ryder and Depp were a 90s power couple for all the goths and weirdoes out there.
The couple was so in love that they tried to get married in 1990 following Depp’s starring role in Cry-Baby. They even asked director John Waters to serve as their minister.
Waters nearly went through with the marriage, Depp’s people even had him ordained as a minister, but the director managed to talk the couple out of it at the last minute. He says that Ryder’s parents thanked him after the fact.
Kate Moss shot in front of the Beverly Hills Hotel for Glamour France, April 1992
Kate Moss is easily one of the most recognizable names and bodies of the ‘90s. Discovered when she was only 14 years old and signed to Storm Model Management, Moss forged a career that changed the way people looked at fashion and turned models into rock stars.
As one of the most photographed women of the ‘90s she was rarely seen in public, but rather in the pages of Vogue or on the red carpet of high profile events where she rubbed elbows with bestie Naomi Campbell and stars like Johnny Depp.
Her slim looks brought “heroin chic” into fashion, giving millions of her fans an excuse to cake on the black eye shadow and draw out their sullen cheeks.
Keanu Reeves and River Phoenix in Los Angeles, 1991
After starring together in Gus Van Zant’s My Own Private Idaho Keanu Reeves and River Phoenix became two of the closest friends that ever were. The two shared an artistic sensibility that’s rarely found in Hollywood. Together, they formed the basis of a kind of anti-brat pack along with Keany’s co-star in Bill & Ted, Alex Winter.
In order to get Phoenix to sign onto My Own Private Idaho Reeves rode across the United States from Canada to Florida to personally hand deliver the script. They were both nervous about the content of the story - gay hustlers living without any money, but Phoenix says that they jumped in feet first together, “We were excited. We just forced ourselves into it.”
Leonardo DiCaprio on set of Baz Luhrmann's 'Romeo and Juliet' (1996)
Canted angles, American accents, gun, and a soundtrack that was straight out of 120 Minutes, Baz Luhrmann’s Romeo + Juliet ushered in a new guard of over the top filmmakers and actors, dead set of turning blockbuster cinema and the tropes of the theater on their head.
It’s impossible to think of Romeo + Juliet as starring anyone but Leonardo DiCaprio, but at the time he said he was unsure about Luhrmann. However, once the two locked into each other’s rhythms DiCaprio knew he was working with the right person. He told Entertainment Weekly:
At first I thought [Luhrmann] was on the pretentious side. But then you start to get to know him and he’s exactly what you want a director to be. Because actors are, you know, completely insecure. They need attention all the time.
Madonna, Sting, and Tupac Shakur, hanging out together in 1994
Prior to the ‘90s the music world was extremely segmented. Rock artists hung with rock artists, pop artists weren’t thought of as cool, and rappers were in their own world.
By the last decade of the millennium pop culture was a place where everyone mixed and enjoyed one another’s company. How else do you explain Sting hanging out with Madonna and gangster rapper Tupac?
Madonna and Tupac dated briefly in the early ‘90s, maintaining a friendship until he was gunned down one year after this photo was taken. The two were together in 1994 when Madonna appeared on David Letterman’s show absolutely went wild. Look it up on YouTube She claimed that Shakur had riled her up before the interview, thus her colorful language.
Monica Bellucci is one of those models that was always around in the ‘90s. Wherever you looked, be it a red carpet for Bram Stoker’s Dracula or the ’97 Cannes Film Festival there she was looking absolutely stunning.
Bellucci began modeling as a teen in the late ‘80s and in the ‘90s her career absolutely exploded when she posed for Dolce & Gabanna the French offshoot of Elle. She also started appearing in European films in 1990, turning her into a household name across the pond.
The Italian Bombshell’s beauty is so stunning that she’s the first thing you see in this photo full of insane visuals. What was the second thing you noticed: those giant sunglasses or the oiled up babe sunning herself?
In the early ‘90s Sean “Puffy” Combs and the Notorious B.I.G. went from living in the projects and working on get rich quick schemes to selling millions of records within a few years.
Combs says that he tried to sell drugs to make ends meet but he was an awful dealer so he got into the entertainment industry. He established Bad Boy Entertainment in 1993 and worked his connections until he was able to convince Arista Records head Clive Davis to distribute his fledging artists.
Within a year Craig Mack had a Top 10 hit and the Notorious B.I.G.’s debut album “Ready To Die” went quadruple platinum… and that was before the label started feuding with the West Coast’s Death Row Records. This musical rivalry would make them into absolutely superstars.
Keanu Reeves kicks up his feet in Paris, " I try not to do anything I don’t want to do."
It feels like we’ve always had Keanu Reeves in our lives, but it was really in the ‘90s when he took on Mount Rushmore of the heart throbs status. Starring in films like Point Break and Speed will definitely do that to an actor, it also helps if they’re inherently lovable.
Following some super serious roles in films like River’s Edge and My Own Private Idaho Reeves took on films that allowed the audience to see him as someone with whom they have a genuine affection, not so much a movie star. When The Guardian asked Reeves how he chooses his roles - especially his bipolar filmography of the ‘90s - he explained:
Honestly, I try not to do anything I don’t want to do. But I guess those movies were in reaction to each other. It wasn’t as thought out as, OK, I finished Point Break, so now I’d better play a street prostitute. It was more like, OK, I finished this, now I want to do that.
Michael Jordan on the set of ‘Space Jam’ in the Jordan Dome, an inflatable dome on the Warner Bros. lot in Burbank, 1996
In 1996 while coming off an injury that caused him to take a break from basketball Michael Jordan was also starring in Space Jam for Warner Bros. Jordan filmed in Burbank and while he wasn’t on set he was in the “Jordan Dome,” a giant tent erected so he could work out, train, and relax while not filming.
To help him get back into competition shape he had basketball players from UCLA brought in to play against him. At the time 19 year old Kris Johnson was in heaven, but he didn’t realize how much hard work he’d have to do after earning his spot in the tent. He told the LA Times:
Michael was not playing any differently than he would play with Scottie Pippen. Michael is very hard on you, and if you don’t have the mental fortitude to deal with that, you will break, as a player and as a person. It takes a strong person to deal with Mike. He got in my [expletive]. It wasn’t, ‘Oh, you’re Marques’ kid. Oh, you’re only a sophomore at UCLA…'
Luke Perry always knew he'd be an actor. He said, "I always felt like I was one of them and in a matter of time I’d get there."
As Dylan McKay, Luke Perry was more than a teen idol. He was a rugged heartthrob who provided a James Dean-esque quality to the world of Beverly Hills 90210 with his pensive line deliveries that rarely rose above a whisper.
Perry grew up in a poor, violent household with an alcoholic father as well as a brother and a sister. As soon as he graduated high school (barely) he got out of his small Ohio town at the age of 17. In 1992 he told Vanity Fair:
I felt like another. It was never about escape. It was aoout wanting to feel like I belonged. I felt like I belonged on a screen. I don’t know why. I guess because I related to the people up on that screen much more than the people around me. I always felt like I was one of them and in a matter of time I’d get there.
Dwayne "The Rock" Johnson and Mankind relax with some Nintendo 64
Anyone watching professional wrestling in the ‘90s remembers the Rock N Sock Connection, a completely off the wall collaboration between Dwayne “The Rock” Johnson and Man Kind AKA Mick Foley.
The duo didn’t make much sense on paper but they were absolute magic whenever the camera was pointed in their direction. Foley says that while the two wrestlers had fun they didn’t realize that they would make such an impact on the lives of their fans. He told Rolling Stone:
We didn’t realize this collaboration would be something that people would talk about with such reverence 17 years later. People can’t name any of our matches, but they think of the way we made them feel. We really had amazing chemistry, not just as opponents but as partners. Neither one of us appreciated it until years down the line.
A reluctant ‘90s queen and style icon, Winona Ryder was a touchstone for theater kids everywhere with her roles in films like Heathers and Edward Scissorhands. Directors styled her in a variety of outfits, but whenever she was photographed off the set she could be found in a leather jacket and a pair of high-waisted Levi's 501s.
Even though Ryder looks cool in whatever she’s wearing she admits that not every look of the era was great. She told Harper’s Bazaar:
It's hard to talk about the influence of the 90s' because I lived through it, so I see it differently than the younger generation. People are obviously carefully cherry picking the better trends - there were a lot of bad looks in the 90s.
Sheryl Lee... the iconic actor who played Laura Palmer in Twin Peaks ⛰️⛰️
In 1990 the question on every television viewer’s lips was “Who killed Laura Palmer?” Twin Peaks was a surreal mystery program that turned America into David Lynch fans and made Sheryl Lee a household name.
Lee was only 22 when she worked on the series and she says that even then she emphatically trusted Lynch and his vision. That’s why she was so disappointed that viewers weren’t able to handle the strange ride the director wanted to take them on.
The actress was so deep inter her character that she still says that it’s hard to separate the timeline of the series from her own life. She told Entertainment Weekly:
When I experience the character of Laura, it’s as one long story. It’s as one life. It’s not broken into first season, second season, Fire Walk With Me, like it is for the viewers. So in my mind, it sort of all runs together.
River Phoenix photographed on the set of My Own Private Idaho (1991)
With My Own Private Idaho River Phoenix and Keanu Reeves proved themselves to be more than just a couple of pretty faces. In order to get the roles they had to prove to director Gus Van Zant that they could play guys who really lived on the streets of Portland.
Van Zant was either going to use the two Hollywood actors or actual street hustlers. In order to prove that they could hang the two actors actually hung out with the hustlers they were portraying. Phoenix told Interview Magazine:
It’s a brotherhood on the street, man. You all watch for each other’s backs. Because no one wants to see anyone get stabbed… It was very sensational for us. I thought our main problem was to find out if we could be the real guys. Gus’ choice was to use real street guys or us, so Keanu and I felt a great burden. We wanted to believe in this script and work out the problems.
Selena in Silver Velour leggings and a Matching Crop Top For a Coca-Cola Campaign in 1994
Taken one year before her tragic murder at the hands of her fan club president at the Days Inn motel in Corpus Christi, Selena was quickly becoming the queen of Tejano. After all, it’s not every performer who gets to appear in an ad for Coca Cola.
The same year that Selena was tapped as a spokesperson for Coca Cola she was nominated for a Grammy Award. She told an interviewer in San Antonio that she couldn’t believe that she was even invited to the awards, let alone up for an award:
When they first told us that we were nominated we all freaked out, we couldn't believe it. The first thing, I promise, the first thing that came to mind is that I need to take a camera to take pictures with all of these stars. It didn't hit me till later when I thought, 'Oh my God. What if we win?’ They didn't let me take my camera in, that's one of the things. I didn't get to take pictures until afterward.
Arnold Schwarzenegger spent hundreds of hours in the makeup chair for 'Terminator 2'
Without a doubt, Terminator 2: Judgement Day is one of the greatest and most important movies of the ‘90s. Even if you’re the kind of person who prefers independent cinema it’s hard to argue against the behemoth that was James Cameron blown out sequel to his small science fiction fiction from a decade earlier.
According to people who were on set at the time of filming the film’s star, Arnold Schwarzenegger, had a thing for walking around in his make up - especially after he started suffering dino damage. Realistically what was he supposed to do, take it off every time he took a break? Chief make-up artist Jeff Dawn told Empire Magazine:
For the original film, he was in 'ripped-apart face' make-up for maybe three days. On this film he's in it for maybe 30 days and it takes about five hours to put it on every day and another hour to take it off. And one thing Arnold says he doesn't like about himself is that he isn't patient enough, but I found him to be extremely patient in the chair. He signed the contract to do this movie and read the script and knew he'd be in the chair for hundreds of hours and I've heard no complaints.
Danny Trejo and Antonio Banderas on the set of ‘Desperado’, 1994
In the early ‘90s Robert Rodriguez made a name for himself with his down and dirty indie movies that focused on telling stories from a Latinx point of view. Even when he was working stars like Antonio Banderas into his pictures he was also casting unknowns like his cousin Danny Trejo.
1995’s Desperado was a followup to ’91’s El Mariachi - a movie made for less than $10,000 - although it’s not as simple as that. The film is more of a spiritual successor to its predecessor. Kind of. Let’s let Rodriguez explain:
This is what The Road Warrior was to Mad Max. It’s like, the same character in a different movie. If you didn’t see the first movie, it doesn’t matter. You can still have a good time with this one.
Robin Williams in Paris, January 1994
In 1994 Robin Williams was coming off a stellar couple of years. Following the success of Mrs. Doubtfire and Aladdin he was laying low and dealing with a bitter feud between himself and Disney. Once Aladdin proved to be a massive hit he believed that his voice was being used for marketing purposes and that he wasn’t being paid.
Initially Disney said that there was no wrong doing, but in a shocking move studio chief Joe Roth admitted that Disney had been uncouth in their dealings with Williams:
Robin complained that we took advantage of his performance as the Genie in the film, exploiting him to promote some other businesses inside the company. We had a specific understanding with Robin that we wouldn’t do that. [Nevertheless] we did that. We apologize for it.
Williams accepted the apology and likened it to “a country re-establishing diplomatic relations.”
