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  • Molly Ringwald on Random Things You Didn't Know About Nostalgic 'It Girls'

    (#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.

  • Liv Tyler on Random Things You Didn't Know About Nostalgic 'It Girls'

    (#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.'"

  • Madonna on Random Things You Didn't Know About Nostalgic 'It Girls'

    (#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.

  • Brooke Shields on Random Things You Didn't Know About Nostalgic 'It Girls'

    (#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.

  • Kate Moss on Random Things You Didn't Know About Nostalgic 'It Girls'

    (#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."

  • Halle Berry on Random Things You Didn't Know About Nostalgic 'It Girls'

    (#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.

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