Leighton Meester’s Prison Past: The Whole Story

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Ramon Martinez takes one you-know-where. Photo: Getty Images

When we learned earlier this month that Leighton Meester was born behind bars, we knew it was only a matter of time before the actress turned the whole story into a positive by using the skills she learned over the last year playing Blair Waldorf on Gossip Girl. And lo and behold, it took less than a month to achieve. Us Weekly talked to her briefly at a charity event and did the background research, pulling together a glamorous cover package.

The story is partially online, but to get the whole thing we had to pick up an issue. Here's the skinny: Leighton's mom, Connie, was arrested for helping to smuggle 1,200-pound shipments of marijuana out of Jamaica in 1983. She was involved in the smuggling ring with her then-boyfriend Doug (Leighton's dad), her father, and her sister Judy. After they were arrested, her sister (Leighton's aunt) broke out of prison and became the first woman in the United States to get on the U.S. Marshals 15 Most Wanted List. Leighton herself was born in a hospital, but Connie had to serve sixteen months in prison afterward.

They were eventually all reunited in Marco Island, Florida, where Leighton spent her childhood before moving to Los Angeles to pursue acting. "She's very gifted, she's very talented, she's very intelligent," Connie now says of her daughter. "I love her dearly." "Anything that her mother and I did that was questionable occurred before she was born," Doug says (he and Connie are now divorced). Even Matthew Settle, who barely shares screen time with her on Gossip Girl, weighed in for Us: "She's proof that the dream can be had by all."

Look what she's done: By giving a few precious quotes to Us Weekly at a party, she landed herself the cover of a popular newsstand magazine and a winning personal narrative. She overcame! America loves overcomers. Blair would be so proud — take that, Blake Lively. Who's the most marketable star of the show now?

Leighton Meester Born in Prison but Mom Was "Always There For Me" [Us]
Earlier: Blair Waldorf Was Born Behind Bars