Random Things You Didn't Know About Nostalgic 'It Girls' (14 items)

• 

  (#1) Liv Tyler

  • 46

  Some girls dream of having a rockstar father, but Liv Tyler ended up growing up with two. Liv Tyler's mother, Bebe Buell, was a singer and Playboy model who had a brief fling with Aerosmith frontman Steven Tyler in 1976. Liv was born the following year.

  While she knew there was a chance Steven was the father of her daughter, Buell named her boyfriend, Utopia singer Todd Rundgren, as the father on the birth certificate. Buell was concerned about Steven's drug use at the time, and said that she and Rundgren "made a pact that he would be Liv's father and if it ever became an issue, we'd tell her at 18."

  But it didn't take Liv that long to connect the dots. She recalls meeting Steven at Rundgren's concert around age 8 or 9, where he bought her a Shirley Temple:

  It must be chemical somehow - DNA and genes... I felt a connection in a very strong way when I met him as a little girl and I didn’t know why at first, but I figured it out rather quickly.

  Liv eventually confronted her mother and discovered Steven was her biological father. She later changed her last name from Rundgren to Tyler and appeared in an Aerosmith music video along with Alicia Silverstone. Aerosmith later debuted their hit "I Don't Want to Miss a Thing" for her film Armageddon.

  While Buell and Rundgren later broke up, Liv still counts Rundgren among her "eclectic mix of parental figures." As she put it, "I’m so grateful to Todd for choosing to be a father figure to me. It's a big thing for a man to say, 'I know this kid might not be mine, but I still want to be her father.'"
• 

  (#2) Winona Ryder

  • 51

  The 1989 movie Heathers is a cult classic that paved the way for a different kind of high school film from the feel-good John Hughes variety of the time. Heathers walked so Mean Girls could run. But despite its endlessly quotable quips, this comedic film about teen suicide that included lines like "f*ck me gently with a chainsaw" had many '80s actors turning it down like the lonely girl at prom.

  One such naysayer was Winona Ryder's agent. Ryder, who played the film's lead, Veronica Sawyer, was a relatively unknown 15-year-old when she got the script. Her biggest film credit at the time was Lydia Deetz in Tim Burton's Beetlejuice, a role nearly the exact opposite of the pretty, popular, serial-killing teen of Heathers. Ryder recalled:

  My agent at the time ­literally got on her knees and begged me not to do [the movie]. She had her hands together, and she goes, “You will never. Work. Again.” We parted ways later.

  Fortunately, she didn't listen. While the film was a box office flop, it later picked up steam on TV and home video, and remains one of Ryder's favorite and most memorable roles. Heathers director Michael Lehmann remembered that the first time he filmed with Ryder, he turned to the cameraman and said, "This girl is a movie star."
• 

  (#3) Halle Berry

  • 57

  Halle Berry was a rising star in the '90s, and if that feels like yesterday, it's probably because she hasn't seemed to age since then. Her memorable acceptance speech in 2002, after becoming the first Black woman to win the Best Actress Award (for Monster's Ball), is legendary Oscar history. But when she earned a Razzie Award a few years later, she managed to make losing look cool.

  Catwoman came out in 2004 and was a huge bust both critically and commercially. Berry later said that she agreed to be the character after a spin-off film for her Bond character, Jinx, was nixed, and she hoped to show that Black women could be action stars and superheroes. The film received multiple Razzies, including "Worst Actress" for Berry.

  While a lot of actors aren't champing at the bit to publicly accept an award for being terrible, Berry was game. She attended the "ceremony" and gave a bitingly funny acceptance speech where she parodied her tearful Academy Award moment and got in on the joke:

  I’ve got so many people to thank, because you don’t win a Razzie without a lot of help from a lot of people... First of all I want to thank Warner Brothers. Thank you for putting me in a piece of sh*t God-awful movie. You know, it was just what my career needed. I was at the top and then Catwoman just plummeted me to the bottom. It’s hard being on top, it’s much better being on the bottom...

  When I was a kid my mother told me that if you could not be a good loser then there’s no way you could be a good winner. If you couldn’t take criticism, then you were not worthy of getting praised. So I ventured into my career of acting; I started off in beauty pageants... and I won the first three in a row... I got to the Miss USA pageant and there I was on the stage with the first runner up... and one of us would win. And she was this buxom, blond, blue-eyed Texan. And I looked her and I thought "Oh God, I’m probably going to lose."

  Sure enough, they called the winner. It wasn’t me; it was her. I looked at her and all I could hear was my mother’s voice in my head, and I thought, "OK, here’s my chance." But all I wanted to do was f*cking slap the sh*t out of her. So, as you can imagine, I want to f*cking slap the sh*t out of these Razzie people that brought me here tonight. But I won’t do that. I’ll do what my mother taught me and I’ll stand here graciously. I’ll take the criticism, take it as a lesson learned, and hope to God I never see these people ever again.
• 

  (#4) Alicia Silverstone

  • 47

  She became an "it girl" playing "it girl" Cher Horowitz. But as a teen, Alicia Silverstone was a far cry from the spoiled but lovable character who made us all go gaga for plaid skirts. An aspiring actress, she dropped out of high school as a sophomore and emancipated herself from her parents at age 15, reportedly to work 40+ hour weeks.

  Speaking to Star News at 18, Silverstone said she had no time to date and was constantly surrounded by adults - her agent was her best friend. When discussing the downsides to her career choice, she said:

  The worst part is having this false attention or having people think they know you or being a commodity to everyone.

  Her ambition paid off, as she worked her way from Domino's Pizza commercials and Aerosmith music videos to leading film roles in The Crush and Clueless. But by 20, Silverstone found herself already jaded with the cutthroat industry.

  Her appearance in the box office flop Batman & Robin earned her a "Worst Supporting Actress" Razzie Award and the unwanted attention of tabloids that ridiculed her body, labeling her "Fatgirl" for her part as "Batgirl." She took a step back from the limelight and "stopped loving acting for a very long time," although the fans never stopped loving her.
• 

  (#5) Drew Barrymore

  • 48

  Drew Barrymore had such an early start to her career that she's rubbed elbows with most of the who's who of Hollywood. And during the early '90s, she was BFFs with Hole singer Courtney Love. Love's child with Nirvana's late frontman Kurt Cobain, Frances Bean Cobain, was born in 1992, and Barrymore was named her godmother.

  While it's not clear what (if any) relationship the two have, they seem to have walked similar paths. Barrymore and Frances were born into famous families and had difficult upbringings, and both were able to achieve sobriety after struggling with addiction.

  In 2007, Barrymore told Jane magazine that she hadn't seen Love or Frances for a few years, but she hoped to reconnect with her goddaughter. She still holds fond memories from her relationship with Love, though. When asked for her best story about Love on Watch What Happens Live, Barrymore recounted:

  Courtney and I were at the backstage of a Seattle club. We’d just come from seeing Green Day. We were going to see Beck play at a coffee house and the bouncer said, "I’m sorry, you can’t come in; you don’t have a backstage pass." Courtney looked at him and goes, "My face is a backstage pass," and then swept him aside and just walked in, and I was just left still standing there, [saying], "I mean, kinda awesome!"
• 

  (#6) Brandy Norwood

  • 44

  Perhaps the only time prom has ever lived up to the hype was in 1996 at Lower Merion High in Philadelphia, where prom-goers were blessed with the presence of Cinderella herself, star of Moesha, no-last-name-needed Brandy, who was 17 at the time. Oh, and her date was a young man by the name of Kobe Bryant.

  Cued up to become the next big thing in basketball, Bryant was a 17-year-old senior when he met Brandy Norwood at the Essence Awards in New York City. At the time, Brandy had already released her first album, toured with Boyz II Men, and was starring on the popular sitcom Moesha.

  Smitten with her kindness, beauty, and intelligence, Bryant later reached out to see if she would go to prom with him, which Brandy agreed to, assuming she could convince her mother, Sonja, to let her attend a dance across the country with a boy she didn't know. A former classmate of Bryant's recalls:

  We were in English class together, and he had one of those teen magazines and it had a picture of Brandy... He showed me and he said, "I'm gonna bring this girl to prom." And I was like, "Whatever, you're crazy." Every day, he would be like "I'm bringing this girl to prom."

  Brandy and her mother ended up flying to Philadelphia, where Brandy, who had a private tutor, got to have the quintessential high school experience, dancing the night away with her peers. She said she kissed Bryant twice, and the pair continued a friendship after prom. Still, conflicting schedules made it hard to take the relationship to a "The Boy Is Mine" level, and Bryant ended up meeting his future wife, Vanessa, in 1999. 
• 

  (#7) Kirsten Dunst

  • 41

  Kirsten Dunst became a teen sensation playing head cheerleader Torrance Shipman in Bring It On and the literal girl next door in Spiderman. But before she graced magazine covers, she made her modeling debut on a book cover in the Babysitter's Club series, circa 1986. She wasn't even old enough to be one of the babysitters; she was actually the toddler babysitter Claudia is holding.

  Apparently Dunst always had a knack for a creepy cover shoot. As she explained to Parade magazine: 

  My first cover was a book in the Babysitter’s Club series, Claudia Gets a Phantom Phone Call. I was a child model/actress and I did it strictly for the money. My first magazine cover was with Tom Cruise in a photo that looked like he was getting ready to suck my blood. That was when I played Claudia in Interview with the Vampire.
• 

  (#8) Brooke Shields

  • 58

  Princeton graduate and official queen of the bold brow, Brooke Shields traced her ancestry on an episode of Who Do You Think You Are? to reveal she's actually royally connected. She explored the rags-to-riches story of her ancestors on her father's side, the Torlonia family.

  The Torlonias, part of the Italian aristocracy, were a wealthy banking family that did finances for the Vatican. Giovanni Torlonia found success as a merchant in Rome and was "adopted" into Italian royalty, despite the fact that he was actually French.

  Never fear though - Shields is also connected to French and English royalty. She's a descendant of King Henry IV of France and is Queen Elizabeth II's 18th cousin once removed. It's unclear if she's been invited to tea.
• 

  (#9) Molly Ringwald

  • 55

  With a career spanning more than four decades, Molly Ringwald has proven her acting chops go far beyond her "Brat Pack" days. She's also a lifelong singer. 

  Ringwald released her first album in 2013, titled Except Sometimes. The jazz record is an homage to her father, jazz pianist Bob Ringwald, with whom she made music from an early age:

  I grew up in a home filled with music and had an early appreciation of jazz... Beginning at around age three I started singing with [my dad's] band and jazz music has continued to be one of my three passions, along with acting and writing. I like to say jazz music is my musical equivalent of comfort food. It’s always where I go back to when I want to feel grounded.

  One of the tracks on Except Sometimes is Ringwald's cover of the Simple Minds song "Don't You (Forget About Me)," the theme from The Breakfast Club that's been stuck in your head since 1985.
• 

  (#10) Kate Moss

  • 49

  Before Kate Moss became "The Face" of the '90s fashion industry, she was just a girl, standing in front of the counter at New York's John F. Kennedy Airport, as her father argued with airline personnel about their repeatedly delayed flight. Meanwhile, Sarah Doukas, who had recently started her own modeling agency, was on her way back to England from a scouting trip. According to Doukas, she was always on the lookout for who might be the next big thing: "Wherever I was going, I was looking. I found a great girl outside a garage in Battersby, in her school uniform."

  The model-hunter spotted 14-year-old Moss before their flight. On the plane, she rushed over to talk to her as soon as the seatbelt sign switched off. The next day, despite her initial reluctance, Moss's mother Linda accompanied her daughter to a meeting at Storm agency.

  Doukas and Moss didn't find immediate success together. While their chance encounter occurred in 1988, Moss's career didn't pick up steam until the mid-'90s. At 5 feet, 7 inches tall, Moss was shorter than typical for the modeling industry, and her "waifish" look didn't fit with the curvier supermodels of the time. "Nobody was interested," Doukas recalled. Eventually, though, Moss left school and committed full-time to modeling.

  While Doukas certainly had an eye, even she couldn't have guessed just how famous Moss would become. "Every day I said, 'I'm going to make you a star.' I didn't know I was going to make her a superstar."
• 

  (#11) Janet Jackson

  • 57

  Carrie-Ann Moss had breakout success from her role as Trinity in The Matrix. But she reportedly wasn't the first pick for the part. The Wachowskis were in talks with Janet Jackson to play Neo's love interest, another fierce and leather-loving lady. Discussing her interest in the role, Jackson said:

  I want to kick somebody's *ss. Anybody's. As long as I get to kick somebody's *ss. Kick a new hole in their butt. Rip 'em a new butthole. I'd love to do that.

  And we would have loved to watch her, but Jackson had a lot going on and wasn't able to take the part due to scheduling conflicts. Her film career never quite took off in the way the sci-fi franchise did - a glitch in the matrix if ever there was one.
• 

  (#12) Madonna

  • 65

  Before she became the fearless, cone-bra-clad "Queen of Pop," Madge was known for stirring up controversy in the American food service industry. In 1978, Madonna dropped out of college to move from Michigan to New York City to pursue a career as a dancer. According to her, she had only $35 in her pocket, although sources from her hometown said she saved up some money for the move working at Baskin-Robbins.

  Either way, in her early days as a fresh-faced New Yorker, Madonna had to slum it, quite literally. She lived in a dumpy apartment in a dangerous neighborhood, and worked many odd jobs before she found her footing. According to Madonna: A Biography, she was fired from Dunkin' Donuts after she squirted filling all over a customer (whether this was accidental or not remains unclear). Later she was fired from her position as a coat checker at the Russian Tea Room.

  And when she joined a dance troupe but didn't like a routine, she quit, confidently stating, "I'm going to be a rock star." At the time, she had yet to sing a note.
• 

  (#13) Gwyneth Paltrow

  • 51

  Many girls grew up wanting to be Gwyneth Paltrow; her natural elegance, warm smile, and proximity to Brad Pitt were just a few reasons why. We too sobbed along with Pitt onscreen and asked, "What's in the box?!"

  If you ordered from Goop, though, what's in the box might be questionable indeed. Beyond her acting career, Paltrow made her "it girl" status a brand when she launched her own wellness and lifestyle company in 2008. While some have found her products, such as vagina-scented candles, off-putting, Paltrow can laugh at her haters all the way to the bank; Goop was reportedly a $250 million company in 2018. 

  Goop got in a little over its head, though, when it went up against literal astronauts. In 2017, the venture released a new product called "Body Vibes" - stickers to place on one's body, which Goop alleged were made with "NASA space suit material." As the website put it:

  Human bodies operate at an ideal energetic frequency, but everyday stresses and anxiety can throw off our internal balance, depleting our energy reserves and weakening our immune systems. Body Vibes stickers (made with the same conductive carbon material NASA uses to line space suits so they can monitor an astronaut’s vitals during wear) come pre-programmed to an ideal frequency, allowing them to target imbalances.

  Tech site Gizmodo went to the professionals to investigate the claims. Mark Shelhamer, former chief scientist at NASA’s human research division, responded, "Wow. What a load of BS this is." Furthermore, NASA responded that space suits aren't even made of carbonate material.

  Goop eventually issued an apology to NASA and removed the claim.
• 

  (#14) Naomi Campbell

  • 53

  When she wasn't strutting her stuff on runways and dominating the fashion world in the '90s, Naomi Campbell was one of several famous faces of the Fashion Café, an ill-fated Planet Hollywood-esque restaurant where patrons could supposedly feel at one with fashion's elite while eating fried food in a chain diner booth. Claudia Schiffer, Elle Macpherson, and later Christy Turlington also joined in on the company.

  CEO Tommaso Buti launched the Fashion Café in 1995, and it soon became clear the restaurant had two sides: one a tacky tourist eatery with prop wardrobe pieces and supermodel-named menu items, and one a private party venue for "it" girls and guys of the '90s. “The $20 Salad Extraordinaire” was reportedly created exclusively for Campbell. The legendary "salad" consisted of a glass of champagne, a pack of Newport cigarettes, two slices of tomato, and a singular iceberg lettuce leaf.

  Sadly, Campbell eventually had to make her salad at home. The four supermodels weren't enough to save Buti from his many financial troubles. By 1998, the Fashion Café shut its doors as Buti faced $15 million in lawsuits from his partners. In 2000 he was charged with a slew of offenses including wire fraud, conspiracy, and money laundering. However, another famous name known to appear at the café was Donald Trump. Before the end of his presidential term in 2021, he pardoned Buti of all charges.

New Random Displays    Display All By Ranking