Leighton Meester, who plays Blair Waldorf on Gossip Girl, was born in a halfway house in Texas in 1986. Meester's mom, dad, maternal grandfather and aunt were all arrested in 1982 on marijuana smuggling and distribution charges.

Three months after Leighton's birth, her mom Connie went back to jail and Leighton stayed with her frateral grandparents until Connie's release.

Connie and Doug Meester were married in July 1982. Busted shortly after the wedding, Doug pled gulity; he spent two years of a four-year sentence at a federal prison in Seagoville, Texas before being paroled in 1984. One month after Doug's arrest, the Feds charged Connie, her sister Judy Haas McNelis and father Robert Haas with smuggling 1,200 pounds of weed from Jamaica. After losing an appeal in 1985, Connie was send to federal lockup in Fort Worth.

Pregnant with Leighton, Connie was transferred to a Dallas halfway house. She gave birth to Leighton on Apr. 9, 1986. She was transferred back to the federal pen three months later.  Leighton and her three-years-older brother, Logan, stayed with their father's mom until Connie was paroled on Nov. 20, 1986. The family soon moved to Marco Island off Florida's Southwest coast, but the parents' relationship deteriorated, and they divorced in 1992.

Connie, who won custody of Leighton and Logan, moved to New York in 1997 with the children. By 1999, 13-year-old Leighton had her first role in Law & Order. Nine years later, she had her breakout role as Manhattan debutante Blair Waldorf on Gossip Girl.

"It's more like my parents' past, not mine," Meester says. "But it make me very non-judgmental and open-minded. And I think it just makes me appreciate the things that I have now."

Meester used marijuana in high school. “I’d do anything but be in school, so I’d skip class," she admits. "I wasn’t dating around, but we’d smoke pot.”