From the outside looking in, Leighton Meester has always seemed like her life has been charmed in just about every way. After all, she beat overwhelming odds to land one of the lead roles in the show Gossip Girl and it was so popular that it is set to be rebooted in the coming months. Of course, there also is no denying that Meester is a gorgeous woman.

As it turns out, Leighton Meester’s family life was a really big mess throughout her child and that problem didn’t disappear once she became an adult. During an interview with Marie Claire, Meester described her family situation in a very interesting way. “My family has a crazy history. Probably the craziest I’ve ever heard of,”

Throughout this article, some of the darkest aspects of Leighton Meester’s life will be explained. Once you learn about everything Meesters has gone through, you likely will realize two things, none of it was her fault and it is amazing that she overcame it all.

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Leighton’s Childhood

When Leighton Meester was born, it is very safe to say that it was under less than ideal circumstances. After all, Meester entered the world in a Texas halfway house because her mother had been sentenced to a 10-year prison term for smuggling marijuana from Jamaica into the United States. Meester’s father also served time in prison because he was a part of the same drug ring as her mom and they smuggled 1,200 pounds of marijuana into America.

After Leighton Meester entered the world, she spent the first three months of her life with her mother in the same halfway house where she was born. After that time passed, Meester’s mother was sent back to prison and Leighton’s grandmother was given custody of her. Even though Meester’s mother was sentenced to 10 years in prison, just like celebrities who’ve recently been able to leave jail early, she was released after only 16 months.

Unfortunately for Leighton Meester, on top of mother and father serving time, some of her other relatives went to prison too. For example, Meester’s grandfather and aunt were a part of the same drug ring and spent time behind bars because of it. In fact, Leighton’s aunt escaped from prison which resulted in her becoming the first woman to appear on the U.S. Marshal’s 15 Most Wanted List. Many years later, Meester’s brother Douglas was charged with sexual assault but unlike his older relatives, he avoided jail time by pleading guilty and paying a $2,000 fine.

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An Unhealthy Relationship

In an ideal world, everyone would have a loving and healthy relationship with their parents. While Leighton Meester will no doubt have that with her children, she didn’t have a great example to follow. Instead, Meester and her mother have had a lot of problems over the years.

After growing up in seedy apartments and having to skip her prom because she couldn’t afford to go, Leighton Meester finally started to make big money. A big-hearted person, Meester cared enough about her family that she began sending her mother monthly $7,500 cheques so that her little brother Lex who has health issues could be taken care of. Unfortunately, Meester learned that her money had been spent on “plastic surgery, Botox, and hair extensions” for her mom instead. Once Meester stopped sending money, her mother claimed they had an oral agreement and demanded that her daughter send $10,000 a month for life. Instead, Leighton took her mom to court and had a judge declare that no agreement existed.

Before Leighton Meester prevailed in court, her mother countersued her demanding $3 million. While it is bad enough for a mother to demand a fortune from their daughter, Meester’s mother went even further by accusing Leighton of assault. According to Constance Meester’s countersuit, Leighton repeatedly “hit her with a bottle” and was so out of control that her brother had to pull her off.

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Amazing Person

Throughout Leighton Meester’s life, she has accomplished an awful lot. Best known as one of the stars of Gossip Girl, Meester played such a key role in that show’s success that it is hard to imagine anyone else in her role. On top of that, Meester has appeared in several movies over the years, including Country Strong, The Roommate, Monte Carlo, The Oranges, and The Judge. Additionally, Meester has released music that charted and performed on Broadway

Despite everything that Leighton Meester has pulled off in her career, her most impressive achievement is coming off like such a great person despite everything that went on in her life. Seemingly very happily married to Adam Brody, Meester seems to be leading her best life. On top of that, Meester’s perspective on her childhood is amazing as evidenced by something she said to Marie Claire about her upbringing in 2012. “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.”

Next: 20 Little Known Facts About Leighton Meester And Adam Brody's Relationship