Being Born in Prison Was Only the Start of Leighton Meester’s Rough Childhood

Leighton Meester rose to fame as Blair Waldorf on the immensely popular show Gossip Girl. These days, she’s continuing to gain fans and viewers through her role on ABC’s Single Parents, another fan favorite. On top of that, her marriage to Adam Brody is largely celebrated by both celebrities’ fan groups and held up as “couple goals.” The pair also have an adorable daughter together.  

With all of that success and adoration, it might be hard to believe that Meester had such a rough start to life. Many have probably heard that the actress was born in prison, but that was only the beginning of a long, difficult road to get where she is today. 

Leighton Meester’s mom was in prison when she was born

In 1986, Meester’s mother, Constance, was in prison. She had landed there after a 1983 arrest for helping her then-boyfriend Doug (and Meester’s father) smuggle marijuana out of Jamaica. The smuggling ring included not only Meester’s mother and father, but also her maternal aunt and maternal grandfather. Meester’s aunt actually became the first woman on the U.S. Marshals 15 Most Wanted List when she broke out of prison. 

Technically, Meester was not born in the prison itself. Her mother was transferred to a hospital for the birth, but she still had 16 months of her sentence to serve after her daughter came into the world. Meester spent the first months of her life in a halfway house before eventually being placed in the custody of her grandmother to await her mother’s release. 

Meester is sanguine about her mother’s past. “My mum lived through a lot before I was born, and I can’t judge her on that. She and my dad are good people,” Meester explained.

Leighton Meester smiling, slightly turned from the camera
Leighton Meester | Rachel Luna/FilmMagic/Getty Images

Leighton Meester had a tumultuous childhood

After her mother’s release from prison, Meester’s parents divorced and the family faced many financial struggles. Meester insists, however, that her childhood was not a bad one. She fondly remembers lots of fun and love despite the money struggles. Her father, speaking after his daughter’s rise to fame, sees her as an inspiration. “She’s proof that the dream can be had by all,” he explained. 

Meester began booking modeling jobs when she was very young and worked for places like The Limited Too and Ralph Lauren. Her family relocated to New York to help her pursue that career, but living in such an expensive city was especially hard. They struggled to pay the bills and keep their basic necessities going. 

The troubling past fueled Leighton Meester’s career

Meester poured herself into her acting career and had to grow up much faster than most kids because of her troubling start to life. However, the actress also seems to see the focus as a kind of gift that helped her channel her energy into becoming what she is today. Even as a young child, she preferred taking acting classes with adults and didn’t relate to immature kid stuff. Her drive was always on becoming successful in her art. 

She did not have much time for a typical teenage social life and missed out on dating. She even skipped her prom. Somewhat ironically, at the age of just 21, Meester would land her big role as high schooler Blair Waldorf and live out some of the moments she never got in real life for all the world to see in her fictional display. 

Her relationship with her mother became strained as she saw more and more success. At one point, Meester was financially supporting her mother and her younger brother, but when she found out her mother was not using the money wisely, she cut her off. What followed was several ugly lawsuits and harsh words. The lawsuits eventually fizzled out, but their existence stands as evidence of the gulf between where Meester’s life started and where it has gone.