Leighton Meester, best known for her indelible portrayal of rich-girl snobbery and capriciousness as Blair Waldorf on Gossip Girl, is getting her bowl on at Frames, a low-key alley abutting the Port Authority, Manhattan’s main bus terminal and one of the last vestiges of Times Square’s gritty past. She enjoys bowling — this is her second outing in a week. Which is not to say Meester is skilled at bowling. Because she is not.
“I never played sports,” she explains, before releasing her ball with an indifferent thump. “I wasn’t any good at them.” She watches the ball drop into the gutter with limp finality. Unfazed, she throws again, hurling it down the lane, knocking over a handful of pins. A second gutter shot follows. “I guess I need a bigger target,” she says flatly.
Meester is no stranger to such things. One of those rare children born with both full-blown ambition and the determination to avoid even the slightest derailment, Meester has been aiming at big game since grade school. Part of this is a rejoinder to circumstance. Meester’s mother, Constance, gave birth to her while serving federal prison time for drug trafficking. Meester was not, she has oft clarified, born in jail. She was delivered in a hospital, then transferred to a halfway house for three months, after which she was sent to live with her grandmother until Constance’s release. Her father, Doug, also served time for drug-related offenses. He and Constance would later divorce. The difficult facts of her childhood provided Meester with matchless perspective. Also, an ineffaceable blueprint of what not to do.
“My family has a crazy history,” she acknowledges. “Probably the craziest I’ve heard of.”
But it was not, she is quick to point out, Dickensian in its misery. “I look back now and I see it in a nice light,” Meester says of her youth in Marco Island, Florida. “It wasn’t uncomplicated. But I played outside. I went to the beach. There were happy, fun times.”
Meester, like many hard-knock kids, has little use for self-pity. “You can take what is handed to you and use it as an excuse to mess up. 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.”
When Meester was 10, she attended a modeling convention in Atlanta during her Christmas break. An agent snapped her up on sight and took her to New York City. “I ended up staying. I never went back to Florida,” she explains. “That was that.”
She lived with her mother in dodgy rentals in the West Village, then in Inwood, at the northernmost tip of Manhattan. Meester booked commercials for Bloomingdale’s, Stern’s, the Limited Too. She flourished under pressure.
“I worked a lot, even though I was just a kid. It seemed normal to me,” she shrugs.
Building on her success, Meester left New York at 14 for Los Angeles for pilot season. She and her mother lived in an apartment at the corner of Hollywood and La Brea, steps from the Walk of Fame, surviving on modest checks from Meester’s grandfather and fees from Meester’s modeling gigs. When she could, she took acting classes. She preferred the ones with adults.
“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.”
Meester stayed laser-focused, eschewing boyfriends for work and study. She took a pass on prom. “It was a lot of money for a ticket. And I just didn’t care that much,” she says. Her eyes were fixed, as ever, on the prize.
“When you see how you react when you suffer,” she explains, “that’s when you know what you are made of.”
For several years, she was a prolific bit player, landing gigs on Law & Order, House, 24, and Entourage. The game changer came in 2006, when she landed Gossip Girl, an audacious, soapy drama adapted from the series of young-adult novels about the salacious lives of spoiled New York City prep schoolers. The show, a breakout hit, is now in its fifth season.
Meester is broadening her scope to film. This summer, she will appear in the Adam Sandler comedy That’s My Boy, in which she plays a neurotic bride who “starts out sweet, then gets crazier and crazier.” It is a familiar refrain. From her spoiled Machiavellian princess in Gossip Girl to the upstart underminer in Country Strong to the sapphic stalker in The Roommate, Meester specializes in elevating unsavory women above the “crazy bitch” stereotype. She doesn’t play the girl you love to hate. She does something far trickier: She makes you love the hateable girl. A quicksilver hybrid of Sharon Stone and Drew Barrymore, Meester has created something entirely new: the beyotch with a heart of gold.
For the full feature, pick up the April issue of Marie Claire when it hits newsstands on March 20.
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