Jimmy Fallon's Big Adventure

The charmed life, troubled times and late-night confessions of the man who found the perfect job

Jimmy Fallon
Photography by Robert Trachtenberg
Jimmy Fallon on the cover of Rolling Stone.
By |

'This is happening," Jimmy Fallon tells himself, as he begins to panic. "This is really happening." He's all of 20 minutes into a brand-new gig as a talk-show host, which suddenly seems to be going as well as his recently abandoned movie career. In other words, badly. Fallon's ill-chosen first-ever guest, Robert De Niro, has decided to take a playfully sadistic approach to their conversation, smirking as he contributes little more than New York-accented monosyllables and the occasional shrug. The interview stalls. Time slows down. (Months later, Fallon's wife, Nancy Juvonen, will describe it as "the longest minute of his life.") As the awkwardness escalates, Fallon feels flop sweat blooming beneath his crisp black suit; his forehead glistens under the hot studio lights. He begins to stammer. His internal monologue speeds up:

"This could go any way. He's right there, and I'm right here. This could go any way. This could be the end of my career."

A lot of professionally funny people are permanent residents in this particular psychological neighborhood, at the corner of self-doubt and self-loathing. But for Fallon, this is just a rare visit. For the most part, he's the least tortured comedian imaginable. "Making comedies, you end up knowing people that you would swear would be the funnest people ever in the whole world," says Juvonen, an energetic blonde who's been Drew Barrymore's production partner for 16 years, and first got to know her husband when he starred with Barrymore in 2005's Fever Pitch. "And they're not. They're really mean and depressed and hideous people. But Jimmy sees life as an opportunity and happiness as a choice. He's cheery in the morning. He wakes up happy. He gets the joke of life." The guy is so relentlessly positive and optimistic that even his own mother says she sometimes finds it overwhelming.

Jimmy Fallon: A Life in Photos

In that first show, from March 2009, you can see the moment when Fallon recovers - when he relaxes, smiles and snaps himself back into focus. He steers the interview back to a prepared bit where he does an impression of De Niro in Taxi Driver (and, in turn, De Niro responds with an effeminate "impression" of Fallon in his 2004 flop Taxi). It kills, and the audience sounds as relieved as Fallon looks. A couple of segments later, he's bro-ing down with Justin Timberlake, trading John Mayer impersonations. All doubt vanishes: The guy can do this. (On the other hand, De Niro signed the show's guest book that day with these encouraging words: "Jimmy, I think you really fucked up. Love, Robert De Niro.")

"I've gotten so much better since Day One - it's not even two years but I know how to handle this thing now. I can do this," says Fallon, who also made a more practical change: "I've lowered the air conditioning in the studio to a point where you can actually store meat in there safely."

This year, while Conan O'Brien and Jay Leno engaged in their noisy late-night war, Fallon kept his head down, kept working. As O'Brien dropped out and grew his beard, Fallon shaved every morning and went to the studio, determined to put on a show. Eventually, with help from his secret weapon, house band the Roots - who fueled ultraviral moments like Timberlake and Fallon rapping through the history of hip-hop - Fallon became the most retweeted, most Hulu-ed, most TiVo-ed man in late night.

Video: Jimmy Fallon Gets Tattooed For His Rolling Stone Cover Shoot

He's also a new breed of talk-show host: He sings (duetting with artists from Bruce Springsteen to Paul McCartney, when he's not leading his crew in their loving Glee parody, "6-bee"); he dances; he impersonates Neil Young; he stars in a serial vampire parody called "Suckers"; he plays beer pong with Betty White; he spends more time thinking about three-minute viral clips than TV ratings.

Having this particular job was never a dream for Fallon - his only real goal in life, the wish he made when he blew out birthday candles, was to be in the cast of Saturday Night Live. He made it at age 23, was a breakout star by his fourth episode, and stayed for six seasons before heading off to try to be a movie star. In many ways, he's picking up where he left off when he quit the show - even reprising old bits such as the "I Wish It Was Christmas Today" song, though this time with the Strokes' Julian Casablancas to help him sing it.

But if anything, Late Night is even more suited to his abilities and temperament. "He has his own show that he uses all his talent on, and he can take it in any direction he wants," says SNL and Late Night producer Lorne Michaels. "I think he understands how well his life turned out." Adds Amy Poehler, one of Late Night's most frequent guests, "He likes to talk to strangers way more than I would ever want to. He's the kind of guy that would go to the airport bar and want to talk to everybody there. His ability to talk to strangers is not necessarily something I relate to, but it's genuine, it's not bullshit. It wasn't invented so he could be good at doing a talk show."

Fallon's designated role is superempowered superfan: geeking out over his endless array of enthusiasms for video games, music, comedy, movies and food. As a kid, he spent hours in his Saugerties, New York, bedroom, working on impressions, listening to Weird Al, Dr. Demento and audio recordings of SNL episodes, and playing guitar. The set of Late Night With Jimmy Fallon sometimes feels like a permanent window on that room - except that he now gets Paul Simon, Steve Martin and Dana Carvey to come over for play dates. "He's like your little brother who wants to do a show for everybody at Thanksgiving," says his old "Weekend Update" partner, Tina Fey. "But he's gotten good at doing the show."

"The one thing that I'm trained to do that the other hosts aren't is I'm more of an entertainer," Fallon says. "I come from a Saturday Night Live background, so I'm used to doing sketches and singing and dancing and doing impressions, and playing guitar, so I should use that to my advantage without being too hammy."

At 36, Fallon is, by far, the youngest of TV's late-night hosts - 11 years younger than his Late Night predecessor, O'Brien, seven years junior to his direct competitor, Jimmy Kimmel. That puts him, and much of his staff, on the younger end of Generation X, but they deliberately chose to embrace the sensibility of an even younger cohort. "Gen X was about the idea of separating yourself from the mainstream," says Late Night producer Gavin Purcell. "It's cool to be part of a bigger thing now. You can do something on the Internet that happens suddenly and is giant and exciting. We kind of feed off of that idea, but not with any sort of irony - we really, genuinely feel excited."

If that's Gen Y thinking, then Fallon was simply born slightly too early. "When he says, 'I'm so excited! So-and-so's coming tomorrow!' he absolutely means it," says Juvonen. "When he says, 'The beautiful, the talented,' he 100 percent means it. Even though he might say that about a lot of people, it's very genuine. It's exactly how he's feeling at that moment. If we're going out to dinner, he can't wait! He loves it there and loves that waiter and can't wait and wants to go back and visit the waiter. It is totally all day long, every day."

Embedded in the ceiling of Jimmy Fallon's corner office on the sixth floor of 30 Rockefeller Plaza is a giant plastic pickle - a gift from O'Brien, who, in turn, received it from David Letterman's writers when he took over the show from Letterman in 1993. The rest of the decor is Fallon's own, though. He's a sentimental dude, so the Oriental rug and wooden desk are remnants from his first Manhattan apartment. A stained-glass portrait of Buddy Holly hangs on one wall (Fallon, who was an altar boy and, pre-puberty, considered the priesthood, has a thing for stained glass).

Radiant-looking photos of Juvonen are everywhere - including a wedding-pic shot on Richard Branson's private Necker Island in the Carihbean, where it was just family and Drew Barrymore - along with pics of Fallon's sister Gloria and her kids and a shot of his parents on the streets of Brooklyn just after their wedding. To the left of two vertically stacked flatscreen TVs is a framed photo of Johnny Carson, looking cool in a blue blazer that matches the Tonight Show curtains behind him. Dr. Oz has taken over the studio that O'Brien used for Late Night, and Fallon uses one next door - which happens to be the studio where Carson filmed The Tonight Show before moving to Burbank. Fallon loves telling people that Tiny Tim's famous 1969 on-air wedding occurred in his studio.

Eight months ago, Fallon was standing outside his office when he heard that NBC's late-night schedule was about to be blown up: He learned the network hoped to move Leno back to 11:30 p.m., O'Brien to 12:05 a.m., and Fallon all the way past 1 a.m. He was relatively unfazed. "Is there a difference? I'm on at 12:37 now," he says. "They think I don't know about the seven minutes after 12:30?" In the end, he stayed at 12:30, and took few lessons away from the debacle. "Conan's working, Jay's working. What's the big deal? Whatever. You're on different networks now. Very good. Is everyone calm now?"

Fallon looks away from his iMac, where he was sending tweets about today's show, and glances out the window by his desk - it overlooks the giant red Christmas balls that just reappeared by the Rockefeller Center skating rink. "The balls are back in town," he sings happily, to Thin Lizzy's melody. "I'm very excited. That means the holidays are here."

The flatscreens serve as computer monitors, too, and Fallon drags a video file onto one of them and clicks "play." It's a proposed bit for the show: footage from Sarah Palin's reality series of her shooting a caribou in the snow - the production team has added a glowing red nose to the animal. Palin killed Rudolph! Fallon watches, aghast. "No," he says.

"Too sad? Too gross?" asks the show's head writer, A.D. Miles. Fallon nods, still looking deeply shaken - he hadn't even noticed the red nose.

Fallon and his team head down the hall to a tiny, cavelike editing room to watch a rough edit of a recurring sketch: "Reflections With Justin Bieber," in which Fallon dons a wig and hoodie to play the 16-year-old pop star - the running joke is that he's unexpectedly concerned about, and well-schooled in, current events: "Y'all want a job in 2030? Y'all better learn some Mandarin!" fake-Biebs says in this one.

When Fallon sees himself in close-up under bright sunlight, he snorts, half-disgusted, half-amused. "I look nothing like Justin Bieber," he says. "It's an old man with a Bieber wig … an old man with makeup." Amy Ozols, a writer for the show, smiles and rolls her eyes. "You're a 36-year-old man playing a teenager - I don't know what to tell you."

Ten years back, Fallon was a not-quite-Bieber-level teen idol in his own right. His life had changed dramatically in 1998, when he blew up as a featured player in his fourth SNL episode, after unleashing his musical parodies (he sang still-funny, if now-dated, Halloween-themed versions of songs by Counting Crows, Alanis Morissette, Matchbox Twenty and Marcy Playground) and a hilariously accurate Adam Sandler impression - which Sandler himself approved after Fallon did it for him over the phone. "It just crushed - it couldn't have gone better for me," Fallon recalls. "I was getting phone calls from people wanting to do movies, wanting to meet with me, phone calls from actresses and peo ple who wanted to date me, fan letters - it was crazy, absolutely nuts." He still has his first 100 fan letters somewhere - he keeps meaning to send the writers some kind of gift for giving him an ego boost - but there was also danger in all the sudden acclaim: "You start thinking you're awesome, when the truth is, you're not."

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.

His laughter fed into a perception that Fallon was some kind of preening ham out to steal attention from other cast members - so the subject still bums him out. "By the end of my last year, it was just such a thing . . . Lorne didn't like it, the writers didn't like it, and I was like, 'I'm not trying to do it on purpose. I'm trying not to do it.' But sometimes it just got insane. I couldn't hold it in, it was just so much fun. I would be giggling and laughing, and usually it was if something didn't work or if someone's wig came off, or I'd look at somebody and start laughing." For anyone who thinks Fallon was doing it on purpose, he offers as evidence a Debbie Downer-goes-to-Disney World sketch in which everyone lost it - including Sanz, who had to wipe tears from his eyes with Mickey Mouse-shaped waffles - and Fallon mostly hangs on until the end.

The real reason Fallon laughed so often on SNL may be simple: He's an obsessive fan of the show, and being part of the cast didn't change that. "He was shaped by it and devoted to it," says Fey. "In his look, even, he has, weirdly, a little kind of Mike Myers in him and a little Dana Carvey, like he was built in a lab to succeed on SNL."

Truth is, Fallon was downright fixated on SNL, skipping high school and college parties so that he could watch it as it aired. He idolizes John Belushi ("That's because he didn't know him," Michaels says, acidly) so fiercely that he once had friends drop him off at the star's grave on Martha's Vineyard with a six-pack, where he spent a couple of hours drinking and thanking Belushi for the inspiration. To this day, he sends Michaels multiple texts about the show as it airs, commenting on matters as arcane as lighting cues.

When Fallon left his small, historically Catholic college a semester early to move to L.A. and start auditioning for TV shows, he never let go of the SNL dream - when he got a tiny role on a WB sitcom, he negotiated a clause in his contract that would release him if he got onto Saturday Night Live. The producers agreed to it only because they found the prospect so unlikely.

Around that time, Fallon made a vow that's hard to square with everything else you know about him. "I remember saying to myself, 'If I don't make it on Saturday Night Live before I'm 25, I'm going to kill myself,'" he casually confesses one night. "It's crazy. I had no other plan. I didn't have friends, I didn't have a girlfriend, I didn't have anything going on. I had my career, that was it."

When Michaels hears about this for the first time, he breathes in sharply, and simply says, "Jesus." Fallon's older sister, Gloria, a writer-turned-stay-at-home-mom, hadn't heard this story before, either, but she's less impressed. "He probably just would have come home," she says, "and become a mailman."

At 12:30 a.m. every weekday, an alarm clock goes off in the master bedroom of the house in Saugerties, New York, where Fallon grew up. His parents, Gloria and Jimmy (who realized too late the potential confusion of giving your kids your own names), jump out of bed, brew some tea, and sit down to watch their son's TV show. They can't quite manage to stay up that late, so they simply interrupt their sleep after a couple of hours. Their son has begged them to watch it the next day on DVR, but they wave him off. They've seen every episode.

Little Jimmy, as his mom calls him, and his sister grew up accustomed to this kind of focused attention. "We were very over-protective," his mom acknowledges. She was the hippieish daughter of a Brooklyn cop; her husband was a former doo-wop singer who volunteered for Vietnam, because he thought it was "the right thing to do." Soon after their kids were born, the Fallons moved from Brooklyn to the sleepy upstate town of Saugerties, where Big Jimmy took a job at the local IBM plant.

As toddlers, Jimmy and his sister played almost exclusively with each other. "We went to kindergarten and suddenly we were all, 'Oh, there are little people just like us,'" says his sister. Even as they got older, they weren't allowed to leave their property without permission - so Jimmy would ride his bike again and again around the perimeter.

"We did it so much that there was a dirt track of where we used to ride our bikes, and I used to listen to my Walkman and ride my bike every day after school in circles," says Fallon. "I felt like Gus the Polar Bear in Central Park. I probably went a little nuts doing that." Around that time, he became obsessed with Dr. Demento and Weird Al - the first comedy his sister found too strange to enjoy.

Fallon was a class clown by sixth or seventh grade, occasionally annoying the nuns at his school. (He asked one sister if her habit was felt - then he touched it and said, "Now it is." She was unamused.) Rather eerily, his eighth-grade classmates voted him most likely to have David Letterman's job someday.

He drank the usual amount of beer in high school, and admits to having done the occasional whippit. But he never got into much trouble. He once disobeyed his parents' direct orders and snuck off on a ski trip. "When he came back, it was totally obvious where he'd been," his sister recalls. "My mom was like, 'Did you go there?' and he was like, 'No,' and she was like, All right.' That's just how it was. He was like Ferris Bueller."

Fallon's not sure what drew him so fiercely to comedy, to making people laugh. "I never went to a therapist," he says. "I don't want to know." But he does venture a guess. "It was a rush. I think it was the rush of getting a reaction. Maybe it's acceptance, maybe it's a thing where you're pleasing somebody. I want to be friends with everybody, and if you make a joke and everyone laughs, you're like, 'That's it, I scored.' That's what I thought making a friend was. You just feel like people liked you, so maybe it was that, acceptance."

As he ponders this, Fallon is sitting at the marble island that dominates the kitchen of his spacious co-op apartment just off Gramercy Park, drinking the second of three Budweisers he'll have tonight. Earlier, he invited me in with a hearty, "Hey, man!" On-air or off, he's an enthusiastic host. "I've got crackers here, cheese in there, beers, wine, Coke. I have orange soda, seltzer, apple juice, tons of beers. Let's do some beers for now. Bud in a can good? Can't beat that." There's also a pizza on the way - he had an assistant e-mail me for my topping preferences.

One of his closest friends, chef Mario Batali (they have a regular squash game that Batali usually wins), helped him figure out the right proportions for the marble island, but Fallon let his wife decorate most of the apartment - the folk art she loves is on the walls, and her rustic taste in furniture predominates. (Before she moved in, Fallon says, the apartment looked like it belonged to an old English lady with a secret passion for video games.) They clearly both take Christmas seriously - there's a seasonal Santa rug on the wood floor, a stuffed snowman on the island and a tree with an inviting array of wrapped gifts.

"I have to show you the bathroom," Fallon says. I follow him in, which feels a little odd, until he shows off the hand-painted silhouettes on the tiles - shadow portraits of friends and family, from his deceased childhood dog to his mom to Shoemaker to Drew Barrymore to Rashi-da Jones. He's trying to figure out a spot to add Michaels' silhouette.

In Fallon's home office is the wooden "Weekend Update" logo from SNL's old set, which Shoemaker saved for him, and a rare Fender acoustic that he used to write most of his comedy songs. Fallon has been playing guitar since childhood, but he never considered a career as a musician - though he does idly dream of spending his retirement as "the guy who plays the acoustic guitar in the bar." In the meantime, he has specialized in getting legendary musicians to do very silly things - from Paul Simon doing an elaborate skit with Steve Martin, to Mick Jagger participating in a Lost parody to, most bizarrely, Bruce Springsteen dressing up as himself circa 1975 to duet with Fallon's Seventies Neil Young on Willow Smith's "Whip My Hair."

But as far as Fallon is concerned, the biggest coup of all may be convincing Paul McCartney to sing "Scrambled Eggs," a version of "Yesterday" based around the scratch lyrics for the song: "Scrambled eggs/Oh, my baby how I love your legs." Fallon had his writers finish those lyrics, writing lines like "Waffle fries/They're like regular fries but shaped like waffles."

Fallon was ready to dress up as McCartney and sing it himself, but after some reluctance, McCartney agreed to do it - with one condition: "I'm not going to do this by myself," he told Fallon. So in mid-December, Fallon found himself sharing a mic with his favorite Beatle, singing absurd food-based lyrics to McCartney's most famous song - and Fallon even gathered the courage to venture a harmony or two (in a rehearsal with a writer standing in for McCartney, Fallon made the whole thing even more insane by singing in his dead-on Mick Jagger impression). That night, Fallon had dinner plans with Michaels - who surprised him by having McCartney show up. The Beatle sat, looked at his new music partner and said, "I think we did good, yeah?"

Recalling this the next day, Fallon still sounds overwhelmed. Once again, he needs to remind himself that it's all really happening. "I haven't had my moment to jump up and down and scream," he says. "When do I get to scream?"

This story is from the January 20th, 2011 issue of Rolling Stone.

From The Archives Issue 1122: January 20, 2011