Celebrities Who Went From Rags to Riches

Leighton Meester

Gossip Girl's Blair Waldorf may come from a family with means, but real-life fashionista and actress Leighton Meester wasn't quite so fortunate. The Texas native's mother was serving time in a federal prison when she gave birth to Meester, though The Oranges actress has since explained that she and her younger brother had a normal upbringing despite their slightly more unusual beginnings.

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