Tragic Details About Leighton Meester's Life

Leighton Meester shot to fame playing sensational socialite Blair Waldorf on the hit show "Gossip Girl."  As the Queen Bee of the Upper East Side, the well-heeled Waldorf was as famous for her conniving and cutting remarks as she was for her couture wardrobe. The role made Meester a household name, but the actor had little in common with her on-screen persona. She did not attend an elite private school or live in luxurious digs. She did not grow up with closets full of designer duds or minions who catered to her every whim. In fact, her real life more closely resembled that of her "Country Strong" character, Chiles Stanton, a beauty queen who has big aspirations and bigger secrets. In an interview with Kidz World, Meester admitted of her role in the 2011 film: "Chiles feels like somebody who I know or maybe a part of myself. She's a lot of things I want to be."

Maybe the reason the beautiful brunette felt so connected to the character of Stanton is because they both had to overcome obstacles and challenges to achieve success. During a press day for "Country Strong" (per The Oklahoman), Meester said: "I relate to her in a lot of ways. I think she's trying to be somebody, and you know, she's driven and kind of sassy, but she also has a past." Meester's past includes tragic details in both her personal and professional lives that date all the way back to the day she was born and have followed her ever since.

The tragic story of Leighton Meester's birth sounds like a scandal straight out of "Gossip Girl." On April 9, 1986, Meester's mother, Constance, gave birth to her now-famous daughter while serving time in a Texas federal prison for her involvement in a drug ring that smuggled marijuana from Jamaica to the U.S.  Though Meester is quick to point out that she was not actually born behind bars, her mother was returned to the slammer to finish serving out her sentence shortly after giving birth. And, because Meester's father, Doug, was serving out his own sentence for his involvement in the smuggling biz, the newborn lived in a halfway house for three months before finally being placed in the custody of her grandmother, who lived in Marco Island, Florida. In an interview with Cosmopolitan, Meester maintained that her now-divorced parents are "good people," saying, "My mom lived through a lot before I was born, and I can't judge her on that."

To add to the scandal, Meester's parents weren't the only ones with a criminal past. Her grandfather and aunt also did time for their roles in the drug trafficking debacle. Her aunt managed to escape from prison, earning herself the distinction of being the first woman on the list of the U.S. Marshal's 15 Most Wanted.  "My family has a crazy history," Meester told Marie Claire. "Probably the craziest I've heard of." 

Following her release from prison, Leighton Meester's mom joined her daughter in Florida where they lived a life that Meester told Marie Claire "wasn't uncomplicated." Even after she was signed on-site by a New York agent at an Atlanta modeling convention, the 10-year-old's life didn't immediately turn into a fairy tale. Sure, she moved to Manhattan and began landing jobs with such big-name retailers as Bloomingdales and Limited Too, but she was still worlds away from a Park Avenue penthouse. Instead of marble-floored buildings with doormen, Meester and her mother lived in small, cheap rentals while the aspiring model and actress spent hours in front of the cameras. "I worked a lot, even though I was just a kid. It seemed normal to me," she told Marie Claire. 

At the young age of 14, Meester and her mom moved to a small apartment near the Hollywood Walk of Fame in Los Angeles. When she wasn't trying to book modeling gigs or take an acting class, Meester was a high school student. But, unlike the popular prep school princess she would later portray, Meester wasn't into the social scene. She didn't even attend her prom because the tickets were too costly. In the same interview, she shared: "I couldn't relate to kid stuff. 'Jimmy doesn't like me!' Who cares? I was worried we didn't have gas money or food. Those were my concerns."

Some roles can make a career and for Leighton Meester, that role was everyone's favorite mean girl, Blair Waldorf. After playing bit parts on popular television shows like "Law and Order" and "Entourage," Meester walked into the "Gossip Girl" audition. While she additionally auditioned for the role of Serena van der Woodson, she felt she was better suited to the role of Blair. To prove it, she dyed her hair brown, and the rest is television history. 

"Gossip Girl" propelled Meester and her cast mates to extraordinary fame and led her to the big screen, where she starred in movies like "Country Strong," "Oranges," "River Wild, and several others. However, the problem with playing an iconic television role for six seasons is that you can quickly become pigeonholed. And although the brown-eyed beauty found her way back to television at the age of 30 in the short-lived Fox series "Making History," she never achieved the same level of success as she did on "Gossip Girl."  The biggest role she has landed since playing Blair Waldorf was that of Angie D'Amato, a single mom on another short-lived show, the ABC comedy "Single Parents." The mother-of-two attributes this fact largely to the stereotypes surrounding women in Hollywood. "I think the perception is: You're an ingenue, or you're an icon, or you're a mom. There's no in between," she told Refinery 29. 

When you have a hit show made up of a cast of young, hot, actors, the rumor mills start churning. Speculation on romances and rivalries, friendships and feuds, is the stuff that sells stories, and there was no shortage of fuel to stoke the fires on the set of "Gossip Girl." Leighton Meester often found herself at the center of the storm, with many people wondering if she and co-star Blake Lively were friends in real life or if Meester was one of the reported celebrities who wasn't a Lively fan. Both actors have denied rumors of tension between them, but they weren't exactly tight by all accounts. The show's executive producer, Joshua Safran, recalls how opposite the girls were and told Vanity Fair: "Blake and Leighton were not friends. They were friendly, but they were not friends like Serena and Blair. Yet the second they'd be on set together, it's as if they were." 

In an interview with New York Magazine, Meester chalked it up to them playing two female leads on the same show, adding: "Why don't they say that George Clooney and Brad Pitt don't get along? It's always the girls."

The tabloids also took aim at Meester's lifestyle, calling her out for drinking, partying, and engaging in public PDA. Whether or not those rumors were true is anyone's guess, but Meester neither confirmed nor denied. 

In "Country Strong," Chiles Stanton finds success as a country music singer. In real life, Leighton Meester's musical career didn't strike the same chord with mainstream audiences. In 2014, she released her debut album  "Heartstrings" and gave a free concert at an Apple store in Soho to promote it. During the Q&A that followed, the singer revealed that the title track was originally inspired by a "stupid breakup" (per Us Weekly) but it evolved. "Now, it really does have more meaning. At the time it was like,' Screw you, I don't care about you anymore, and it's not going to happen! Joker.'"

While it may have been her first album, Meester had been making music for many years. Most notably, she lent her vocals to Cobra Starship's 2009 hit, "Good Girls Go Bad," a catchy pop tune that landed in the top 10 of Billboards Hot 100. That same year she joined forces with the "Blurred Lines" singer  Robin Thicke for her single "Somebody To Love."  "Heartstrings" was a vast departure from those previous pop efforts in both sound and style, leaning into a contemporary folk vibe. The album did not break into the Billboard Hot 100, but that couldn't have been a huge surprise for Meester who told Billboard, "This [new album] is for people who don't know anything about my acting and don't listen to pop music" 

When Leighton Meester shared that her song "Heartstrings" was based on a bad breakup from years past, it was tough to narrow it down. That's because prior to her romance with Adam Brody, which resulted in what appears to be a happy marriage between the former "Gossip Girl" and "The O.C." stars, Meester wasn't always lucky in love. She has been linked to a string of famous faces, including Sebastian Stan, who played Carter Baizen in "Gossip Girl." Some speculate that he is the "joker"  she refers to as the inspo for her song "Heartstrings," given their relationship timeline and the fact that she referred to their breakup in Seventeen magazine (per Us Weekly) as "really hard" and "really sad." 

Meester was involved with a few other hot hunks before settling down with Brody, including her "Country Strong" costar Garrett Hedlund. There were also rumors swirling around her relationship with her "Gossip Girl" love interest Ed Westwick aka Chuck Bass, further fueled by the fact that, unlike his character, Westwick couldn't seem to stop professing his love for Meester during interviews. Both denied any off-screen romance, and Meester was very clear about the fact that she didn't like relationships, once even telling Glamour UK (per In Style) "I've hated every boyfriend I've ever had." Clearly, that was before she met her now husband, Brody. We can't help but wonder what he did to make her change her tune. 

What should have been a hit based on its star power turned out to be Leighton Meester's biggest flop and the film that some say derailed her entire career. "The Roommate" was a "Single White Female" type thriller that starred Meester and Minka Kelly as, you guessed it, roommates. The predictable plot and slow storyline earned the movie an abysmal 3% rating on Rotten Tomatoes, with audiences giving it a mere 27% rating. The critic consensus determined that the movie "isn't even bad enough to be good." Although the film was panned, Meester was praised by one L.A. Times critic for the nuances of her portrayal of a manipulative stalker that illustrated, in his words, "how much more she is capable of." 

Maybe her portrayal was so spot on because Meester knows what it's like to be the object of someone's obsession. As Blair Waldorf on "Gossip Girl," she was both loved and hated by the throngs of fans who tuned in each week to see what the Manhattan socialite would do next. But it wasn't just the fans who were obsessed. Meester recalled one paparazzi member who took things too far by managing to sneak onto the "Gossip Girl" set and into the star's trailer while she was sleeping. In a joint interview in Interview, Adam Brody recalled that his wife woke up to find the photog standing over her, an incident she referred to as "creepy."

In something that sounds like it's ripped from the"Jerry Springer" show, Leighton Meester and her mother became embroiled in a legal battle over the misappropriation of the $7500 the actor sent home each month to help with the cost of caring for her younger brother, Alexander "Lex," who lives with serious medical issues, per TMZ.  Rather than use the money for Lex's health care, Meester alleged that her mother spent the money on herself, indulging in cosmetic procedures and other pricey beauty treatments. According to ABC News, Constance countersued her famous offspring for $3 million, claiming that Meester had been physically abusive and "hit her with a bottle" repeatedly until Lex intervened. She also tried to convince a judge that she and her daughter had entered into a verbal agreement where Meester would fork over $10,000 monthly to her mother for the rest of her life. 

Meester's mom eventually dropped her abuse claims, but the actor stood her ground. In 2012, Los Angeles Superior Court Judge Gregory Alacron ruled in favor of the "River Wild" star, saying that there was no binding agreement and that Meester was under no obligation to pay her mother anything. While the ruling was a victory for Meester, it was not a win for the relationship, which had already taken a hit in 2008 when Meester fired her mother as her manager due to disputes over finances. 

The lawsuit between Leighton Meester and her mother garnered plenty of press, and Constance Meester used the attention to paint a very ugly picture of an ungrateful daughter who she claimed abandoned her family in their time of need. Constance told In Touch that she gave up everything to help make her daughter's dreams of stardom come true. "I never told Leighton this, but I worked as an exotic dancer to make ends meet," she said.

Prior to their legal battle, Meester had been sending her mother thousands of dollars each month to help with care of her younger brother, Lex. However, Constance told In Touch in 2011 that she was "destitute" and just steps away from living on the streets. "My car was taken away," she said, "My house has gone into default, and we can't afford food. I only have $26 left." She also claimed that she was "pretty sure" she had lymphoma, although it had not been confirmed by doctors.

In the end, Constance's sob stories and bids for attention seemed to have no bearing on the legal matters since the court found in favor of Meester. However, Lex may be the biggest loser in this case since it is unclear whether his medical needs were being properly met once the money dried up.

In addition to asking a judge to determine that she did not have to pay her unemployed mother any more of her income, Leighton Meester included a request for custody of her younger brother, Alexander "Lex" Meester as part of her 2011 lawsuit. When Meester realized that the money was instead being used on cosmetic procedures, a source close to Meester told Radar Online that the actor was "disgusted," adding, "She wants Lex to leave their moms California home and come to live with her in New York." Although a judge ruled in Meester's favor on her request to end any financial obligations to her mother, the custody ruling is unclear. However, since Lex does not appear to reside with his sister and her family, we assume she was not granted custody. 

It is also unclear as to what became of Constance Meester following the court's decisions. Although she once told In Touch that she was "looking at homeless shelters," after being cut off from her daughter's purse strings, according to the lawsuit, "Although Constance is healthy and physically able to work, Constance refuses to do so." Hopefully, she has found a way to support herself and, more importantly, get Lex the care he needs.