20th anniversary cover gals, 1999

January, Gwyneth Paltrow

The actress - who won an Oscar for her performance - was starring in Shakespeare in Love when she appeared in a pink and gold lace dress by Versace on our cover. At 26, the new mom already saw her kids growing up differently than her. "My children will have a different life from mine," Paltrow said. "My father always says when he was a kid, you had Maine lobster in Maine. Now the world's homogenized. It's all in the mall."

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February, Cindy Crawford and Rande Gerber

The model couple kicked off our February issue by sharing photos from their hush-hush wedding ceremony in the Bahamas. Crawford, then 31, wore a John Galliano slip dress for her walk down the aisle. "I chose the Galliano and had it lined, because it was very see-through," she told us. "I also had a Valentino dress I loved, but in the end I wore the Galliano. Rande liked it better because it was shorter! So that's what he got."

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March, Drew Barrymore

After 23 years in the acting biz, 24-year-old Barrymore started a new career as a producer with her first feature film, Never Been Kissed. "The work was so much fun," she gushed to InStyle. "It was so great. It takes up every second of your time and you never get upset for a second. In fact you're like, 'More, more - more hours in the day!" On our cover, the star wore a Heidi Weisel dress and Cartier earrings.

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April, Charlize Theron

The highly sought-after actress, then 23, was promoting The Astronaut's Wife, The Yards, and The Cider House Rules when she appeared on our cover in a Gucci dress. In the issue, Theron talked about the importance of creativity - especially in her vocation! "It sounds like such an actor thing, but as an only child on a farm, keeping yourself busy and entertained has a lot to do with your imagination," she said "I just always believed it was possible to live your life that way."

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May, Calista Flockhart

The 34-year-old star was appearing in William Shakespeare's A Midsummer Night's Dream with Michelle Pfeiffer and Kevin Kline when she appeared on our May cover (in a flirty Cynthia Rowley dress). When we interviewed her, Flockhart confessed to being a little stubborn. "That's so in my nature," she told us. "If somebody tells me not to do something, I'll do it faster, louder and bigger than ever."

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June, Jennifer Lopez

The triple threat - actress, dancer, and singer - has just released her debut album, On the 6, when she appeared as our cover girl wearing a Calvin Klein swimsuit. Lopez, then 29, told us the secret to her sound. "You have to have heightened emotions," she the Bronx beauty. "If you're really happy, angry, depressed or in love, you can write a good song."

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July, Claire Danes

The 20-year-old Ivy League student was starring in Brokedown Palace when she took time off from classes to talk to InStyle. "Here, at Yale, you're supposed to mess up," Danes said. "In Hollywood, they'll let you make few mistakes. But they'll jot it down." The ethereal beauty wore a Dolce amp Gabbana dress for our cover photo.

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August, Cate Blanchett

The busy actress was starring in An Ideal Husband, The Talented Mr. Ripley, and David Howe's play, Plenty, but still managed to find time to appear as our August cover girl (wearing an Elspeth Gibson dress). Blanchett, then 30, didn't mind her hectic schedule. "I know how privileged I am to be in a position I never expected to be in," she told us. "I am so lucky to be doing what I love."

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September, Jennifer Aniston

For our September issue, Aniston talked about what being sexy means to her while wearing just a bedsheet on our cover. "Nobody thinks of themselves as sexy, really," the 30-year-old star said. "Some days you go, 'Hey, I'm not doing too bad today.' But if you try to be sexy, you'll never be sexy."

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November, Antonio Banderas and Melanie Griffith

Griffith, then 42, was starring in Another Day in Paradise, Celebrity, and Lolita when she appeared with her 39-year-old husband on our November cover. "I'm happier now than I've ever been," said the glowing Mrs. Banderas.

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December, Lisa Kudrow

For our last cover of the century, Lisa Kudrow (then 36) talked about the upcoming new millennium while wearing a Valentino dress. Her big New Year's Eve plans? That was still up in the air! "If I didn't have a baby, maybe I'd go to a fabulous New Year's party. Maybe I wouldn't. Who am I kidding?"