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Jimmy Fallon's Big Adventure

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For all of Fallon's charisma, his presence isn't larger than life - it's more precisely life-size. But as he sweeps into Manhattan's Gramercy Tavern, a few blocks from his apartment, after taping a show one Tuesday, that's more than enough: He came straight from the day's taping, but he's changed from his suit into slacks and a checked button-down (he favors the designer Rag & Bone). He hugs the hostess, shakes the maitre d's hand and greets everyone by name, practically down to the busboys. As a steady stream of amuse-bouches and other extras arrive at the table, he seems genuinely grateful for each one. "It's so rad, you're going to freak out," he says as the venison tartare he urged me to order arrives. "It's off the charts, right? It's so good."

When Ahmir "?uestlove" Thompson, bandleader for the Roots, began working with Fallon, his thoughts echoed mine at this moment: "His personality borderline scared me, because I was like, 'OK, he's too nice,'" he says. "The first month, I'm waiting for the other shoe to drop, for this farce to be over with. I kept waiting for it and waiting for it." Almost two years later, ?uestlove is still waiting.

If Fallon ever had a chance to turn into an asshole, it was during his run as the cute, hip guy in his SNL cast. He indulged in what he now reluctantly describes as a "fun hang, nothing serious" with Winona Ryder, released an album of comedy songs, tore through downtown bars with his drinking buddy Horatio Sanz, and hosted the VMAs, parodying Eminem, Dave Matthews and Nelly for a crowd of shrieking teens - all the while headed toward what seemed like inevitable movie stardom. After scoring a solid cameo as a band manager in Cameron Crowe's Almost Famous, he told an interviewer, "Ideally, I'd like a Johnny Depp career, with a Mike Myers background."

Starting in 2000, Fallon took on an SNL role he had never imagined for himself, hosting "Weekend Update" alongside Fey. In 2003, there was a hint of things to come: When David Letterman came down with shingles, Fallon guest-hosted.

Longtime NBC late-night exec Rick Ludwin asked Fallon not to do it. "Frankly, I didn't want anybody else getting ideas about Jimmy, because I thought he was going to do a good job guesting for Letter-man," Ludwin says with a laugh. "I was saying, 'I don't want other people getting ideas about you, I want you to be the Late Night host on NBC" By the time Fallon finally left the SNL cast the next year, O'Brien was striking a deal with NBC to take over The Tonight Show in five years, leaving his own show open. After some discussions with Lorne Michaels, Fallon kept the possibility in the back of his mind, but moved ahead with his movie career.

Taxi, his movie with Queen Latifah, is an easy punch line now, but the studio had huge expectations for it - its critical and box-office failure was a sucker punch for Fallon, the first flop of a charmed career. One review still sticks in his head: "I remember one guy said, 'I'd rather drop a DVD player on my nut sack than have to sit through Jimmy Fallon in this movie.' He got his point across," Fallon says.

Despite his fondness for Taxi, Fallon is witheringly harsh in assessing his own performance ("The only person I've ever seen Jimmy be rough on is himself," says Michaels). "I was a bit confused doing that movie," Fallon says, "because certain scenes, I wanted to be Richard Pryor, in Stir Crazy. And then other scenes I was really into Serpico. I was watching it every day. I don't know if that's the right movie to watch when you're doing a comedy, but I was trying to channel Al Pacino. The great dramatic actor of comedy!"

Fallon was charming opposite Barrymore as a crazed Red Sox fan in his next movie, Fever Pitch, and it got better reviews. But it also flopped, and Fallon's career as a leading man was suddenly dead. "Everyone was like, 'He had his shot, he had two movies, and that's your shot in Hollywood,'" says Fallon. After that, he filmed a not-so-good indie movie with Sharon Stone and Lucy Liu, and co-wrote what sounds like a clever, still unproduced screenplay "about a guy in a goth band who has to pretend to be a country-music star." Somewhere in there, he went through what he claims was a "fat phase," gaining all of 10 pounds. "I was probably drinking too much," he says.

Box office and barhopping aside, he just wasn't enjoying Hollywood. "Movies are hard, man - I really don't like doing movies," he says. "You sit in a trailer and you have makeup on and you just wait - then they're like, 'You've got to come out and be funny,' and you do a scene and go back and wait again for the next scene, and you're there 15 hours. I'm not good at it. I miss the immediacy, I miss the response."

NBC was ready to figure out a way to let Fallon do the occasional movie along with Late Night - but he went all in. To prep for the show, he went back on the road, doing stand-up for the first time in years. He started watching DVD box sets, "old Chevy Chase, I watched old Dick Cavett, I watched Johnny Carson, lots of The Larry Sanders Show, almost every Larry Sanders. It's the most realistic take at what we do."

Fallon was ready for his third act. "I realized I could keep doing stuff in movies and making a living, it's good money and all - and I was doing artsier things, less comedic work, which every comedian, in a weird way, wants to do," he says. "You always want to do what you're not good at. But I had enough of it. I did things that I'm not good at for a while, and then I was ready to get back in and try and take a good crack at doing this and making it work."

It's not hard to make Jimmy Fallon laugh - which, under normal circumstances, is a winning trait: On a recent Late Night episode, a relentlessly foulmouthed Joan Rivers made him crack up so many times that he had coughing fits and seemed in danger of falling out of his chair. "That's part of why he's charming," says a key collaborator, Michael Shoemaker, who was a Saturday Night Live producer for almost 20 years before leaving to executive-produce Fallon's talk show. "Because he makes you feel funnier."

But during Fallon's SNL years, the laughing thing was a problem. Though some of his friends, like Amy Poehler, insist he was singled out for something that happened to everyone, he became infamous for an inability to keep a straight face. It started with his difficulty delivering his only line in Will Ferrell's legendary "More Cowbell" sketch - it didn't help that Ferrell had unexpectedly come out in a bellybutton-exposing shirt, putting Fallon over the top. After he gained a reputation, Ferrell and others would mess with Fallon, deliberately trying to get him to break character: In a repeated sketch where Ferrell and Rachel Dratch played lovers in a hot tub, Ferrell would reach down under the water and give Fallon's leg a sensuous squeeze.

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