Now: Winona Ryder
These days, she is known for her character in Stranger Things. She once got engaged to Johnny Depp, though the actress never ended up marrying anyone. However, she and Scott Mackinlay Hahn has been together for several years. In 2000, she got her very own star on the Hollywood Walk of Fame.

Now: Winona Ryder
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Then: Kate Moss
Kate Moss has been hailed the baddest fashion queen of the 90’s. She was discovered at the tender age of 14, but she made it to the top not long after. Aside from her Vogue covers, people remembered her heavy drinking and drug use.

Then: Kate Moss