Leighton Meester has been to the top of the Empire state Building twice—once to the walled-in tourists-only Observation Deck, and once to the very, very top, where, she reports, there are these really low ledges, and you just stand there and take in the view while holding on to hooks.
“You mean: You, the sky and give or take 1,250 feet between your head and the pavement?” I ask.
“It’s unbelievable!” she insists.
Happily for me, today we’re only headed to the Observation Deck. It’s a clear, sunny afternoon, and we’re tooling around Manhattan visiting the sites of several famous only-in-New York movie scenes. Our itinerary might be a little gimmicky—Iconic New York Actress Pays Homage to Previous Iconic New York Actresses—but Meester doesn’t seem to mind and has come dressed for the job in a loose gray Isabel Marant sweatshirt, J Brand skinny jeans (“More like jeggings,” she jokes), dark hair tucked inside an Autumn Cashmere floppy knit hat (“My hair is a rat’s nest when I wake up—but I slip this thing on and people think it’s a fashion statement!”), black flats (“In case we end up walking a lot”). Picture her Gossip Girl alter ego Blair Waldorf kidnapped from the Upper East Side, deported to the East Village and forced to shop at Urban Outfitters.
Which, as it happens, is a step up from Meester’s pre-Waldorf self. “My friend says that before the show I dressed like a homeless person,” she says. “I used to buy everything at garage sales. It was hard to give up! I’d be like, ‘But this crazy sweater is amazing, and it only cost 25 cents!’ ” Waldorf’s influence hasn’t turned her into a fashionista by any stretch—off-hours, Meester is the low-key, comfort-first type who does most of her shopping online or when traveling, and she only uses a stylist for red-carpet events. “I’ve learned from Blair, though. Now I like to pepper in something designer”—she tugs at her Isabel Marant sweatshirt—“with my usual stuff.”
When we step off the elevator, the high-speed winds tear my carefully done chignon into a whirling catastrophe. I attempt to say something witty and end up with a mouthful of hair (my own). As we push through the crowds for a gawking spot, the serenely be-hatted and hair-not-flying-anywhere Meester affects a posh, old-timey accent and quotes from the 1957 classic An Affair to Remember—“The Empire State Building is the closest thing to heaven in this city!” (In the movie, a besotted Cary Grant waits dejectedly on the Observation Deck for his presumptive bride-to-be, Deborah Kerr, oblivious that she’s a no-show because—sorry to ruin it for you—she’s been hit by a car.) As we take in the city arrayed below, searching out our favorite buildings (Meester’s is the Flatiron), her tone quickly morphs from self-consciously campy to wistful—the first of many such mood shifts I’ll witness. “That heart-racing feeling!” she says of Grant’s plight. “You want him to know what she’s going through.” As I’m absorbing this, she grabs my shoulders and cries, “Make it shine like the top of the Chrysler Building!” I look at her uncomprehendingly. “That one’s from Annie,” she explains, and it dawns on me I’m traveling with both a glamorous movie star and a straight-up film geek.
Meester may have swanned into our consciousness as the breakout star of Gossip Girl, but as the show stares down what may be its final season, it’s becoming increasingly clear that the 26-year-old actress is both of the Gossip Girl brand—really, its irreplaceable center—and also something beyond it. Her movie roles don’t look anything like Blair Waldorf, whom The New Yorker’s ever-astute Janet Malcolm called “an anti-heroine of the first rank: bad-tempered, mean-spirited, bulimic, acquisitive, endlessly scheming, and, of course, dark-haired.” It’s a testament to Meester’s range that she’s already played a Southern beauty queen-turned-country singer alongside Gwyneth Paltrow in Country Strong and costars as a beleaguered bride-to-be who bellows things like “Throw it, you big vagina!” in this summer’s That’s My Boy alongside Adam Sandler and Andy Samberg. Seriously: a Sandler movie. How does that work exactly? Meester’s preternatural poise doesn’t seem a natural match for gross-out comedies targeting adolescent boys of all ages.
The obvious explanation is that she’s talented. When I ask Cecily von Ziegesar, who wrote the teen novels Gossip Girl is based on, whether Meester has met her authorial expectations, she gushes: “I don’t know how she does it! Blair was always my favorite character in the books, and Leighton embodies her perfectly. It would be so easy to make her a stereotypical bitch, but instead Leighton gives her a softness and intelligence and almost”—and here’s the key—“a physical comedy, too.”
As the day unfolds, I come to see exactly what she means. Given the nuance Meester brings to Waldorf, I wasn’t terribly surprised to discover that, in person, she is thoughtful and reflective, eager to follow our conversation wherever it takes us and even appealingly considerate, cheerfully going along with our ambitious schedule in spite of having just come off an epic day (shooting the last episode of season five of Gossip Girl). But I completely did not expect her to be a ham. A delightful, exceedingly attractive ham, but a ham nonetheless.
It’s this side of Meester that Sandler saw and encouraged in That’s My Boy. “It’s different than anything I’ve ever done before,” she says, “100 percent comedy, very funny, super-raunchy.” Shot in and around Boston and Cape Cod, the movie is about a deadbeat dad’s (Adam Sandler) opportunistic decision to re-enter his wealthy son’s (Andy Samberg) life on the eve of his wedding (to Meester). “Adam is so personable, so good to everyone. I’ve never been able to improvise my own jokes and lines before, but Adam created an environment where that could happen.”
By now we’re in a hired Lexus on our way to Tiffany & Co.—in homage, naturally, to Blair Waldorf’s dream-life devotion to Breakfast at Tiffany’s (and everyone’s favorite, Holly Golightly). From the side, Meester resembles your standard super-pretty twentysomething, but whenever she faces me head-on I’m distracted by her astonishingly long eyelashes. It gets to where I can no longer restrain myself: “Are those things for real?”
“Why, yes!” she purrs, batting them for effect. Then she leans forward to gently inform the driver that he’s missed our turn. Apparently while I’ve been admiring Meester’s natural beauty, we’ve cruised right past Tiffany’s without my noticing. Oops.
“I’ve stopped wearing makeup when I’m not working,” she continues, kindly ignoring my poor cruise-director-ing. “For a while I thought I had dark circles and bad skin, and then I realized I was seeing myself that way because I didn’t recognize myself anymore without makeup. Now when I wear it, I think I look really weird!” The car comes to a halt. “Here we are!”
At 2 pm on a Tuesday the legendary jewelry store is far more like a busy train terminal than Audrey Hepburn’s glamorous “safe place.” We zip upstairs, where it’s a little quieter, and Meester shows me where she performed her own songs for Fashion’s Night Out 2011. There’s footage of the event on YouTube: Meester demure and glowy in a long white Carven dress, her soft voice nearly drowned out by the excited shrieks of her fans.
“A little-known fact is that when I’m performing, I like to wear a bodysuit beneath whatever I’m wearing,” she confides out of nowhere. “I hate bras, at least when I’m singing. But don’t include that!” (I plead; she relents.) Meester’s songs are folksy and feminine; she cites singer-songwriters Alison Kraus and Joni Mitchell as inspirations for her acoustic-driven melodies and lyrics about love and not-love, and hopes to release a record of her own by the end of the year. “When I was a kid and picturing myself making music, this is exactly what I was picturing,” she says.
I float my current theory, that adulthood is a process of returning to whoever we were at age six, and Meester nods vigorously in agreement. “When you’re little, you’re at your most honest and welcoming and playful. Acting and writing and singing—everything I’m doing now—I’m finally doing it exactly how I always wanted to,” she says, sounding both grateful and a little astonished. As we wander around peering into glass cases glittering with jewels, I find myself wondering about her romantic life; I know she’s single, and something I’ve read somewhere makes me think she has a cynical attitude toward love, which, it turns out, couldn’t be further from the truth. “I love love,” says Meester. “It’s the most intriguing universally understood emotion, and it comes in so many forms: family love, love of friends. I fall in love with everybody all the time.” Has she ever wanted to be married? “Not yet.” Could she envision never getting married? “Yes! Especially now that I know you don’t have to be married to have children; when I was a kid I thought marriage was sex,” she says, laughing. “But if I ever am in a situation where I want to be married, I don’t think I’ll have a big wedding. Hopefully it would be about something way more secure than that.”
Like most serious-minded, hardworking celebrities, Meester is a bit of a homebody. She lives alone with her trusty sidekick, a long-haired dachshund named Trudy, who travels with her between her apartment in New York and a house in Los Angeles. “I used to have roommates all the time. Living alone—it’s so great to get to know yourself, and how weird you are, which can be pretty weird... You can be like, ‘I spent all day watching that?!’ ”
Most of the watching involves cooking shows; Meester prefers cooking at home to going out, and constantly trolls Chopped! and the Cooking Channel for ideas. “I loooove Giada De Laurentiis and Nigella Lawson, and Gabriele Corcos and Debi Mazar are so charming and funny and make everything look super-easy,” she sighs. When she pulls her lipstick out of her purse, it’s coated in herbs—such are the perils of bringing one’s own popcorn seasoning to the movie theater. Meester brushes off the oregano and shrugs.
At long last (as in, time for a late lunch), we’re downtown at Katz’s Delicatessen—home of the famed, er, climax of When Harry Met Sally. We place our orders at the counter, then find the one magically empty table amid the melee and sit down with our heaping plates of corned beef and pickles, which might just be the second closest thing to heaven in this city. It’s been such an exhaustingly crowded afternoon, yet even so we’ve been left alone in our little bubble of chatter; I suspect that Meester’s floppy knit hat not only (a) hides her messy hair and (b) protects it from high-speed winds but also (c) serves as a disguise. Yet after a while the recorder on the table between us gives her away; for the first time all day a few fans come over and ask for her autograph. Meester smiles and stands up and poses for pictures.
Her graciousness—with her fans, with her interviewer (me, that is)—is striking; it’s as if, back when she was a little girl on a tiny island in Florida picturing her grown-up life, Meester was preparing for this part too: the fame. So when she sits back down, I ask her, “Did you always know you’d be successful?” She pauses for a minute, and the clatter of dishes and cutlery and line cooks barking orders fills the air. I realize that owning up to one’s ambitions isn’t particularly comfortable—most of us are trained to be modest—but I have the sense that Meester will treat my question with the same candor and self-possession that have marked our day together. “I don’t know. Yes?” she finally ventures. “But you can’t count on success in this business. And anyway, being famous or rich or making a certain kind of movie—none of that means ‘success’ to me. Success to me is being happy and fulfilled, truly fulfilled, and being proud of myself and doing different things all the time. So thus far, yes, I’ve been successful.”
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