“My family has a crazy history": The crime-riddled childhood of Gossip Girl's Leighton Meester.

When Leighton Meester first bellowed into our homes, her words were terse, her character bratty (“Haven’t you heard? I’m the crazy bitch around here”) and her fashion high-end.

The crown of her head was almost always adorned in a headband of sorts, her legs in white tights, her hands covered in gloves. The semblance was money and a lot of it.

She was Blair Waldorf, the Gossip Girl star and anti-hero for millions of teenage girls; bitchy but likeable, high-maintenance but loyal, stubborn but passionate.

Such is the reality of having your breakout role become a pop culture icon, over the coming years, the public would struggle to separate the actress from the acting.

Early magazine profiles of Meester were awed by the fact the actress was nothing like the character she played.

GQ noted, wondrously, that Meester was “free from pretension” in 2009. That same year, Cosmo wrote she is “surprisingly unsnotty” and – I quote – “SO not a bitch…!” When Byrdie profiled her in 2017, journalist Amanda Montell made note of the “juxtaposition between Meester’s natural self and the glitzy characters she’s played on-screen”.

There were others, of course, more explicit: “Leighton Meester’s Low-Key Style Would Horrify Blair Waldorf,” orLeighton Meester’s Go-To Legging Look Is Very Anti–Blair Waldorf”.

The consensus was one, the same and loud: Leighton Meester was nothing like her iconic character Blair Waldorf.


Meester, the woman who brought Waldorf to life so spectacularly, came from a different realm in a different world at a different time.

Leighton Meester, aged 17.

Meester, now 33, was born in 1986 while her mother was in prison. In 1983, her mother, Constance, was arrested after helping smuggle shipments of marijuana out of Jamaica. Constance's then-boyfriend (Meester's father) was part of the smuggling ring, as was her sister and her father.


New York Magazine reports after their arrest, Constance's sister broke out of prison, becoming the first woman in America to find herself on the U.S. Marshals 15 Most Wanted List.

Meester was born in a hospital, she has clarified in many interviews, rather than within the confines of a prison cell.

Her mother, however, had to serve sixteen months in federal prison after her birth and Meester was transferred to a halfway house for three months. After that, she was sent to live with her grandmother until her mother's release. Her parents soon divorced.

“My family has a crazy history. Probably the craziest I’ve ever heard of,” she once told Marie Claire in 2012, giving rare insight her childhood. “I look back now and I see it in a nice light. It wasn’t uncomplicated, but I played outside, I went to the beach. There were happy, fun times.”

She touched on the need for her to grow up quickly, too. Her concerns as a kid, she says, weren't superficial. She didn't have time for that.

From Dawson's Creek to Gossip Girl, we take a look at the most ridiculous things that happened on our favourite teenage TV shows. Post continues after audio.

“‘Jimmy doesn’t like me!’ Who cares? I was worried we didn’t have gas money or food. Those were my concerns.

"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.


"Look, I could've turned out a lot worse."

At the age of 10, Meester began modeling after signing with an agent. She moved from Florida to New York City. At 14, they moved again, once again for her career, landing in Los Angeles. She spent much of her teens auditioning for TV pilots and taking acting classes.

In a 2012 interview with Cosmopolitan, Gossip Girl executive producer and writer Stephanie Savage says she had noticed Meester for some time before her first audition. Her work ethic gave her a reputation, and her reputation was a good one.

"She has a great combination of intelligence, wit, and strength but also this mischievous quality," she said. "Leighton's very matter-of-fact and upfront about things, and unlike Blair, she's nonjudgmental."

Though as Meester's career grew, her relationship with her mother began to deteriorate. In late 2008, it was reported mother and daughter ended their informal business relationship. Meester did, however, commit to sending her $7,500 every month to care for expenses regarding her younger brother - particularly medical ones.

Leighton Meester and Adam Brody. Image: Getty.

Three years later, the actress filed a lawsuit accusing her mother of misusing the funds to pay for cosmetic surgery for herself instead of paying for her brother, Lex's medical care.

Constance counter-sued, claiming she and Meester had a verbal contract stipulating she would pay $10,000, not $7,500. She also claimed she was owed a larger sum for "sacrificing her own happiness" when she moved Meester to Los Angeles as a child to pursue acting.

Though Meester won the lawsuit the year later, it did not stop her mother speaking on the public record about her relationship with her daughter.


“I knew that she was going to be a star and I devoted my life to making sure that happened,” she told InTouch Weekly in 2012. “I never told Leighton this, but I worked as an exotic dancer to make ends meet.”

In 2010, Meester met actor Adam Brody, in 2014 the duo married and a year later, they welcomed a daughter named Arlo Day Brody.

She is as famously private about her family as an adult as she always has been about the ones who raised her.

“I don’t talk about Arlo very much,” she told Refinery29 last year. “I am very proud of that area of my life. But I’m also really proud of the show, and of the work I do. I think the perception is: You’re an ingenue, or you’re an icon, or you’re a mum. There’s no in-between."

Notably, she also commented on the idea that women are rarely considered more than an extension of their husbands and their babies. But that, she says, is a mistake. Women are far more than a product of their family that raised them, and a product of the family they create themselves.

"The excitement for a lot of people is: Man and woman meet, get married, then have a baby. But in the meantime, there’s so much more to women. We have these flawed heroes so often leading shows. But a flawed heroine? She’s portrayed in a different way: so much more of a bitch, and if she’s older, certainly a dried up one."

The picture the magazine world paints of Meester, as it's perhaps the only world that gets the occasional insight into who she is as a person, is one of confidence, no fuss, unbridled talent and straight-shooting honesty.


More than anything, though, comes the message that Meester is far more than the environment in which she was raised. Sure, it's worth noting that it's remarkable to rise above the hurdles haphazardly placed around her childhood and adolescence, but it's as equally important to recognise Meester, the actress, singer, mum and wife, as more than a tabloid punchline. More than actress with a backstory that rivals fiction.

"You can take what is handed to you and use it as an excuse to mess up," she said in 2012. "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."

And then, as she told Harpers Bazaar in 2009:

"You know, I'm trying to think of what I'm ashamed of. But, damn, I don't really have any shame."

In March 2020 it was widely reported, thanks to a series of paparazzi photos, that Leighton is expecting her second child with husband Adam Brody.

This post was originally published on March 16, 2018, and updated on April 2, 2020.

For more gossip celebrity news, sign up for our "Mamamia Celebrity" newsletter. The best entertainment stories of the day to help you unwind.