Goldie Hawn’s spawn, Kate Hudson, would eventually be blessed with sun-kissed Californian good looks, but things didn’t start off so hot for the starlet. Before the 30-year-old’s groupie antics in Almost Famous and rom-com hijinks in How to Lose a Guy in 10 Days, Hudson was a very awkward red-carpet accessory for her mom.
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As a child, Oscar-winning humanitarian George Clooney suffered from Bell’s palsy, a disease that results in a slight paralysis of the sufferer’s face. While there’s no forgiving those glasses, the ER star eventually made a full recovery and pioneered the renaissance of hot docs in scrubs.
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Although somehow she looks younger now than when her career first began, 46-year-old Twitter-obsessed Demi Moore once had a string of bad films and an even worse baggy pants phase.
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Jerry O’Connell was famously a chubby, pre-pubescent kid when he starred in Stand by Me but he got the last laugh when he married former supermodel Rebecca Romijn. Child stars—they’re never just like us.
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30 Rock mastermind Tina Fey wasn’t always smokin’, which makes her ascension into pin-up status even more satisfying. During her early days on SNL, Fey joined Weight Watchers (truly) and dropped nearly 30 pounds, providing a boost of confidence that landed her in the Weekend Update anchor seat. And the rest is history.
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Mary Kate and Ashley Olsen were supposed to be the cute comic relief on Full House, but in reality, their goofy hairstyles were more giggle-worthy. The two are still building their tween-to-teen empire and basking in their millions, so they seemed to get the last laugh. We only hope they avoid the daily reruns on ABC Family.
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Jeff Gordon ascended to NASCAR fame in the 1990s despite sporting one of the most unbecoming swaths of facial hair the world has even seen. After a clean shave and a few Daytona 500 wins, the much more chic speed demon married hot Belgian model Ingrid Vandebosch.
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Before she became America’s Sweetheart, Julia Roberts had a wild mane of hair in Mystic Pizza, and a wardrobe any grandmother would envy.
No one could imagine Daniel Craig, the gangly boy with a bowl haircut seen here, would breathe new life into the James Bond franchise—or create such an iconic moment by emerging from the ocean in a turquoise pair of swim trunks.
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Granted, this isn’t technically an ugly duckling phase, but when future Sexiest Man Alive Sean Connery wanted to shed his dashing James Bond image after Diamonds Are Forever, he made this unfortunate career choice, 1974’s Zardoz. What Goldfinger and Blofeld couldn’t accomplish, this outfit surely did. Goodbye, Mr. Bond.
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