Leighton Meester appears to have it all, including a successful acting and music career, a solid marriage with The O.C. star Adam Brody, and an adorable daughter named Arlo. Although she’s well-known for playing the role of the uber-affluent Blair Waldorf on the hit series Gossip Girl, Meester’s real life is far from picture-perfect.
From the time she was born — while her mother was serving time for drug smuggling — through her formative years in a halfway house and sketchy rentals, the actress has endured incredible financial and emotional hardship. Her relationship with her mom has been a nightmare that includes court battles over money and custody of her little brother. Her romantic history is rife with hardship and loneliness, too. Meester has openly admitted through interviews and songwriting that her glittering Hollywood life has, at times, been a complete facade.
Here is the heartbreaking truth about her tragic life.
Her mother gave birth to her while doing time
It’s hard to imagine that Meester lived anything other than a charmed life. After Gossip Girl came to an end in 2012, she focused on her music career while simultaneously starring in the Broadway play Of Mice and Men. Meester clearly has the drive to succeed at anything she puts her mind to, yet from the time she was born, the cards were stacked against her and many probably expected her to go down a very different road in life.
Meester was born in April 1986 in a Texas halfway house while her mom was serving a prison sentence for smuggling drugs. In an interview with Us Weekly (via Fox News), the actress revealed that her mom, Constance, gave birth to her at the start of a 10-year prison sentence for smuggling marijuana from Jamaica into the United States. Constance was later released after serving just 16 months.
Meester has taken her rough start in stride. "I think it just makes me appreciate the things that I have now," she told the publication.
She spent her early years in a halfway house
After Meester’s birth, she and her mother remained in the halfway house for three months, according to an interview the actress gave to Marie Claire. After that short period of bonding, Meester’s mom was sent back to prison to finish out her sentence.
Meester’s dad was dealing with legal issues of his own (we’ll get into that in a bit), so she was released to the custody of her grandmother, who raised her until Meester’s mom was released.
A lot of her family members have broken the law
Let’s get back to Meester’s dad. When Meester’s mom was arrested on drug charges, she was reportedly working in conjunction with Meester’s dad, Meester’s grandfather, and the actress’ aunt. Everyone was busted, but Meester’s aunt became the first woman placed on the U.S. Marshals’ 15 Most Wanted List after she escaped from prison, according to Us Weekly (via New York magazine.)
The cycle of crime trickled down to the next generation. Meester’s brother, Douglas, was charged with rape in 2002 after he was accused of sexually assaulting a fellow cadet at the Air Force Academy in Colorado. The charges were later dropped in exchange for Douglas entering a guilty plea and paying a $2,000 fine, according to ABC 7News Denver.
She grew up living in ‘dodgy rentals’
After her mom’s release from prison, mother and daughter settled in Florida, but Meester had dreams of leaving the state behind and making it big in the entertainment industry.
At age 10, she attended a modeling convention in Atlanta during her school’s Christmas break. After an agent signed her on the spot and asked her to move to New York, she and her mom wasted no time pursuing the budding star’s dreams. "I ended up staying [in New York], Meester said to Marie Claire. "I never went back to Florida… That was that."
But Meester and her mom had trouble making ends meet. Meester booked gigs with major stores and brands, including Bloomingdale’s and The Limited Too, but the pair reportedly lived in "dodgy rentals" in the West Village and Manhattan’s Inwood neighborhood until the big checks started rolling in.
Those seedy apartments are a far cry from the real estate properties Meester has scooped up later in life. In 2011, she purchased a beautiful $1.45 million home in Encino, Calif.
There’s no doubt she’s living a true rags-to-riches lifestyle.
She couldn’t afford to go to prom
By the time she was 14, Meester had left New York and moved into an apartment with her mom in Hollywood, Calif. They were barely able to get by with the payments they received from Meester’s modeling gigs and with money her grandfather sent them.
Meester told Marie Claire she stayed focused on her career mainly because she couldn’t relate to what kids her age were going through. "I was worried we didn’t have gas money or food. Those were my concerns."
When prom time rolled around, Meester realized the tickets were way too expensive and she "just didn’t care that much," so she decided to skip out on the event.
Looking back on her decision, we doubt she regrets skipping that formal. She has since been invited to glamorous industry events that most of us can only dream of attending, such as the 2016 Met Gala, where she was photographed rubbing elbows with industry elite, such as famed designer Peter Dundas.
She sued her mom for ripping her off
Meester’s relationship with her mom took a dramatic turn in 2011. The actress and singer had reportedly been sending her unemployed mother $7,500 every month to help provide adequate care for her little brother, Lex. Instead of using the money on her brother, Meester accused her mom of blowing the monthly payment on "plastic surgery, Botox, and hair extensions," according to TMZ.
When Meester cut her mom off and refused to send more money, her mother tried to convince Meester that they had an oral contract requiring her "to pay her $10,000 a month for life," reported TMZ. Her mom also reportedly threatened to file a lawsuit against her daughter unless Meester continued to make the monthly payments. Meester apparently felt the only way to settle their disagreement was to file a lawsuit of her own.
A judge agreed there was no contract between mom and daughter, and in June 2012, Meester was vindicated when she was told by the judge that she didn’t have to pay her mother another dime, according to ABC News.
Her younger brother has health issues
The main reason Meester was sending her mom money in the first place was reportedly to help care for her little brother, Lex, who was dealing with some serious health issues, including recovery from brain surgery. The money was to be used for Lex’s medical bills, which is why Meester was "disgusted" when she found out her mom was using the payments for other purposes, according to an insider who spoke to Radar Online.
In the 2011 lawsuit against her mom, Meester also asked for custody of Lex. A source told Radar Online, "She wants Lex to leave their mom’s California home and come to live with her in New York… Leighton is really close to her brother, so she just hates that she can’t be there to help him more."
The terms of the custody battle were not revealed, but in 2014, it was clear that Lex had remained in his mom’s custody. Constance told InTouch that after Meester cut her off financially, her home went into default, she couldn’t afford to buy food, and she and Lex began searching for homeless shelters. "I only have $26 left. If something doesn’t happen soon, we’ll be homeless by the holidays," Constance told the magazine. Meester’s mom also said doctors were "pretty sure" she had lymphoma.
We hate to see families battling, so we can only hope Meester and her mom will eventually establish a peaceful relationship and Lex will receive the care he needs.
Her mother accused her of assault
Speaking of that lawsuit Meester filed against her mom, Constance made some shocking claims when she countersued her daughter.
After the checks stopped coming in, Constance filed a $3 million countersuit to get the money she felt Meester owed her. She also alleged that things got physical between them during a heated argument. According to ABC News, Constance accused Meester of repeatedly hitting "her with a bottle" in December 2010. Constance said things got so bad, Meester’s brother had to pull them apart.
According to the Daily Mail, Constance eventually dropped her countersuit.
She always had trouble dating
It’s pretty unbelievable that someone as beautiful as Meester would have a tough time in the dating world, but the actress and singer revealed to Seventeen magazine (via People) that she struggled to find "the right fit in a romantic relationship."
Before getting engaged to and secretly marrying The Oranges co-star Brody (pictured right,) Meester said, "I’ve never really liked anybody before. Even when I would date guys, it would sort of be on the surface and it was always a relief when we broke up."
She also revealed the only time she was ever really crushed when a relationship came to an end was when she parted ways with her Gossip Girl co-star and ex-boyfriend, Sebastian Stan, (pictured left.) She turned the heartbreak into a learning opportunity. "I’ve only had one experience where it was really hard and I was really sad when it ended, but that’s what taught me a lot about myself and love and life–and that’s good."
Is she ‘desperately’ lonely?
She spends a lot of time in the spotlight, but that doesn’t mean Leighton Meester doesn’t suffer from bouts of loneliness. In October 2014, while performing and engaging in an Q&A session at the Apple Store in NYC (via Us Weekly,) she opened up about a song she wrote called "L.A." Meester said the song represented a period in her twenties when she was putting on a complete facade.
The actress said, "[The song] sounds really happy, and it’s really sort of sweet… But it’s totally fake… It’s about living in L.A., and being like, ‘Oh look, I’m an adult. I have material things. I have a home and friends and I’m a grown up! But I’m just desperately lonely.’" She described the song as being very "personal," and she hoped that other people would hear it and be able to relate to the "painful" times she went through.