15 filthy rich celebrities who were once homeless (With Pictures)

13. Leighton Meester

Leighton Meester, famous for her role on Gossip Girl, was not always the doe-eyed starlet we know and love today. She was born during her mother’s stint in jail for drug smuggling charges. Her mom, Constance, was allowed to be remanded into the care of a halfway house while giving birth, where she and her newborn daughter lived for two months before she was brought back to jail. Leighton lived with her grandparents until her mother finished her sentence. They all moved to LA together were Meester started modeling and acting at about age 14. Things were finally looking up when she started landing TV gigs. Nowadays, Meester is worth about $5 million and looks like she has no plans of slowing down.