When you think about Leighton Meester, you most often associate the Hollywood starlet with her iconic performance as Blair Waldorf on the teen drama Gossip Girl.
For six seasons, Leighton portrayed a spoiled rich girl at the center stage of Manhattan's elite. Her character was born into privilege, as she wore the finest clothes, ate at the most expensive restaurants, and spent money like water.
However, Leighton’s real-life upbringing couldn’t be further away from her fictional alter ego’s lavish lifestyle.
Leighton was born on April 9, 1987 to a mother behind bars. Her mother Constance Meester had been sentenced to a Texas federal prison for drug trafficking. She had been involved in smuggling 1,200 pounds of marijuana into the U.S. from Jamaica.
29-year-old Constance gave birth to Leighton in a hospital before being transferred to a halfway house for three months. Leighton was then sent to live with her grandmother until her mother was released 16 months later.
However, Leighton’s mother wasn’t the only family member involved in criminal activity. Her grandfather, aunt Judy McNelis, and father Douglas Meester had also served time in prison for the roles they played in the smuggling ring.
Following her arrest, Leighton’s aunt escaped prison and became the first woman in the United States to get on the U.S. Marshals 15 Most Wanted List, New York Magazine reported.
Despite admitting to not having a “normal” childhood, Leighton maintained it was a happy one in Marco Island, Florida.
"I look back now and I see it in a nice light," Leighton told Marie Claire. "It wasn't uncomplicated. But I played outside. I went to the beach. There were happy, fun times."
She also said she refuses to let her upbringing define who she is today.
"You can take what is handed to you and use it as an excuse to mess up. But I've always handled what was given to me by life. I consider myself lucky. I was never lied to. And I was loved," she added.
In 2010, Leighton spoke highly of her mother to Grazia magazine, and even called her her “inspiration.”
“My mother Connie inspires me. She's an amazing woman,” Leighton said. “When I was a kid I wanted to be an actress and she completely backed me. She is her own person, very eccentric, very individual.”
However, their relationship would take a nosedive the following year when Leighton took legal action against her mother.
Leighton had sued Constance over the financial support she gave her, to help care for her sick younger brother, Alexander. In her lawsuit, Leighton claimed she gave her mother $7,500 a month to help cover Alexander’s health expenses, but she spent it on plastic surgeries, Botox, and hair extensions instead.
Constance filed a countersuit totalling in $3 million worth of damages, stating she had “sacrificed her happiness” for her Leighton’s acting career, only to have her daughter renang on her financial promises. She said she has spent $230,000 over the years for Leighton to attend private school and acting classes.
Constance’s suit claims there was a legal deal where she would receive $10,000 a month from Leighton. Due to medical issues, E! News reported Constance has been - per the Welfare and Institutions Code - a "dependant adult," and was eligible for parental support.
She argued that she was the president of Intentional Productions, Inc. (IPI), which managed Leighton’s career, and had an oral contact with Leighton's attorney, Marty Singer, to testify in a previous lawsuit between her daughter and her former talent agency, Abrams Artist Agency.
Constance also said the actress tried to turn Alexander against her, and had threatened to stop making making payments if he didn’t move away from her.
In response, Leighton said that IPI was merely a "loan-out" company, and Constance played no actual role as her manager. Leighton also said that the alleged oral agreement made by her lawyer was meaningless as “it's illegal to bargain for testimony to win a lawsuit.”
The actress also said her mother didn’t have any merit to sue for "dependent adult financial abuse," arguing if their the traditional mother-daughter roles had been reversed, Constance would have needed a guardian to sue on her behalf.
At the end of the year, Constance withdrew her countersuit and Leighton received a default judgement in her favor. In June 2012, Meester subsequently won the entire legal battle, when the judge rejected her mother's claims of the alleged agreement.
Surprisingly Leighton had not sued her mother to retrieve any of the money she had originally given her for her brother, but instead to keep her out of her life for good.
Since then, life has significantly improved for Leighton. In 2014, she married her The Oranges co-star Adam Brody, and welcomed their daughter, Arlo Day Brody the following year.