Drew Barrymore
The original New York It Girl is also our favorite Hollywood underdog story. The former Hollywood wild child spent years reveling in the streets of the city. Several stints in rehab didn't hamper Drew's success. She built upon her experiences and published a tell-all memoir at an age when the rest of us were just going to bat mitzvahs and quinceañeras.
Drew has certainly had her ups and downs, but now is back and better than ever. She has a beauty line, has an established career in film and is one of the most likable stars in Hollywood. Oh, and she's moved uptown to a luxe Park Ave apartment. #Winning
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