15 Celebrities With Shockingly Tragic Pasts

8. Leighton Meester

This young and talented actress portrays Blair Waldorf on the popular television series “Gossip Girl” and her career seems to be escalating quickly, but this actress has one unusual secret.

Namely, Leighton came into the world in a rather weird way, well, place actually – behind bars.

Her mother was in prison at the moment, serving time. In fact, the whole Waldorf family was in prison when this blessed event occurred, because of their rather unusual and pretty much illegal hobby.

Leighton’s mom, Connie, Leighton’s dad, Doug, Connie’s sister and her father as well were all arrested for smuggling 1,200 pound shipments of marijuana from Jamaica in 1983.

After they were arrested, her sister (Leighton’s aunt) broke out of prison and became the first woman in the United States to get on the U.S. Marshals 15 Most Wanted List. How about them apples? Nice family business, wouldn’t you think?

Ok, Leighton wasn’t actually born in prison, her mother was taken into hospital for the very childbirth, but her mother was in the middle of her sentence and still had to serve 16 more months of her prison sentence afterward.

They were eventually all reunited in Marco Island, Florida, where Leighton spent her childhood before moving to Los Angeles to pursue her career in acting. Some seriously huge gossip on the Gossip Girl.