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My New York: Jimmy Fallon

Jimmy Fallon

Jake Chessum

Jimmy Fallon's new show, Late Night with Jimmy Fallon, brings a new attitude to late-night television.

Jimmy Fallon’s New York has always laughed at him. “I used to be hung over every Sunday after Saturday Night Live,” he says. “And I would go to this bar in Midtown for a little hair of the dog, and every Sunday—it was a tradition—I would walk by this great fire station on Eighth Avenue and they would make fun of me.” Fallon shifts into a De Niro-New Yawk accent, approximating the firefighters’ Sunday morning critique: “Hey, what was that ting you did last night on Update? Dat was so dumb.” Or, “What’s wrong wit your hair? You wearin’ a wig?” Or, “What, you laugh at your own jokes?” Once in a while, a compliment: “That ting you did wit Mick Jagguh last night—dat was funny!”

Fallon is in his office on the seventh floor of 30 Rockefeller Plaza. It’s Friday morning, the last day of the first week of his new job as the host of his new talk show, Late Night with Jimmy Fallon. Fallon has replaced Conan O’Brien, who is in turn replacing Jay Leno on NBC’s The Tonight Show. With his famously tousled hair and impish baby face, Fallon’s ensemble—crisp blue slacks with light blue button-up shirt and respectable businessman’s shoes—looks back-to-school new. You get the impression that his boss, Lorne Michaels, just gave him the once-over. You also get the impression that Fallon is exhausted, although he retains a buoyant, eager-to-please energy. You can see him—feel him!—scrutinizing you for visual cues of approval.

“Now it’s just about making it more comfortable for everybody,” he says about the coming days and weeks. “Because this isn’t like a normal new job.” He takes a beat. “Dude, my parents were here. My aunt and uncle were here. Everybody sends you flowers and balloons and champagne.” He pauses to check your status before building steam again. “It’s an unavoidable big deal. You’re cool. You’re centered. You’re great. But you can’t control the outside world. I walked into my dressing room and it felt like I had my appendix out—there were Mylar balloons covering the ceiling.”

In some ways, Fallon’s attitude—call it active responsiveness—is something different for late-night television. It’s a shift from ironically closed-off big daddies Letterman and Leno; even from the absurdly self-conscious Conan. There is just something about Fallon, something cute. Not look-at-those-dimples cute, but, aww, he really-wants-us-to-like-him cute. He might be the first bona fide cute late-night talk show host.

And do you know who enjoys cute? Women. You can see it in the way Fallon’s female guests react to him. In the first week, Tina Fey, Cameron Diaz and Drew Barrymore all fawned over him in the same way high school girls fawn over the cute, sweet flirt on the basketball team. Sure, women fawn over Letterman and Conan, too—but not like this.

Do you know who has a problematic relationship with cute? Men. It’s no secret that Fallon is dealing with a sort of cute backlash. Red Sox fans still haven’t forgiven his soaked-in-treacle turn in the baseball romantic comedy Fever Pitch. Most egregiously, in recent years, SNL fans have saddled Fallon with a reputation for “breaking”—cracking up—in the middle of skits.

Although he blames this last allegation on Will Ferrell (“It’s all because of that Best of Will Ferrell DVD”), he does admit: “I’m an easy laugh.” He’s always been an easy laugh, he says, from the times he hosted SNL viewing parties every Saturday night during college to laugh at Phil Hartman and Adam Sandler, to his years on the show itself, laughing at his buddy Horatio Sanz or across the stage from Will the Thrill. And now he’s laughing at his own show, even when unintentional, like during that awkward inaugural interview with Robert De Niro or when Donald Trump wouldn’t read the cue cards during a skit.

“And I’m not faking laughter,” he says, actually looking concerned about this line of questioning. “Jon Stewart laughs. Letterman laughs. Everybody laughs.”

Aww. He’s cute when he’s angry.

This article has been adapted from the original, which appeared in the June 2009 issue of Sky.

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