Leighton Meester Celebrates Her Gotham Magazine Cover

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." Source

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