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Last Night With Jimmy Fallon: Into the Wee Hours With the Heir to TV’s Grandest Franchise

Photo: Martin Schoeller

The Polar Vortex has coated the pavement outside 30 Rockefeller Center in black ice, but it’s toasty inside, where Jimmy Fallon, ­delivering one of his final monologues as host of NBC’s Late Night, is going down in flames. “Pope Francis recently invited sixteen rabbis to have lunch with him at the Vatican,” Fallon begins. “Then they got a minister, walked into a bar, and blew everybody’s minds!” A smattering of halfhearted claps rolls through the audience, a response so pathetic that Questlove, leader of Fallon’s house band, the Roots, tries to help out with a drum kick. Fallon attempts the punch line again: “A pope, a minister, and sixteen rabbis walk into a bar!” Silence.

Steve Higgins, his announcer and sidekick, jumps in: “I think the rabbis said, ‘You get the check, we’ll get the tips.’ ”

Massive groan. Higgins scolds the audience: “Oh, come on! Seriously?”

“I get it,” says Fallon. “Tips.”

“Yeah, because of the mohels,” says ­Higgins. “Abraham made a pact with God!”

Everyone else in the studio is still confused, but Fallon’s laughing so hard he can barely keep it together: “It’s a classic circumcision joke.” Higgins says something about foreskins turning into suitcases; another massive groan. “This will all be cut out,” a mock-indignant Higgins promises the audience. “Enjoy it now!” he shouts. “Tell your friends about it.”

Of course it won’t get cut out, in the end, because what’s more entertaining than watching professional comics fail wildly onstage? “No one got that!” Fallon tells me later, delighted. “I got the joke. But it was a long walk. It was so funny to watch that bomb.”

Ever since he dropped on to our comedy doorstep, a 24-year-old on Saturday Night Live who couldn’t help but crack up in sketches and yet somehow managed to make breaking character the funniest part of the joke, people have talked a lot about Jimmy Fallon’s earnestness—his unmistakable delight in doing what he’s doing. But it might be his sketchiness, if you will, that really sets him apart. Unlike the other hosts he’ll soon be competing against at 11:35 p.m., when he takes over Jay Leno’s job as host of The Tonight Show on February 17—David Letterman on CBS, a fast-ascending Jimmy Kimmel on ABC, and the niche dual-snark whammy of Jon Stewart and Stephen Colbert on Comedy Central—Fallon has spent every week for six years putting on a chaotic live variety show where his own success hinged on persuading Holly­wood’s most famous stars to go down the rabbit hole with him.

Sure, he’s done stand-up, too; right out of college, he’d take a bus from his aunt’s in Fort Hamilton to do sets at Carolines comedy club in Times Square, and he did nightly gigs at every stop on his recent tour of NBC affiliates. But he isn’t really a joke-teller so much as a performer who just says “yes” to everything: He can sing, dance, and play a mean guitar, and does such loving, reverential pop-culture-geek impersonations that celebrities will gamely get in on the joke and send up their own images right next to him. He doesn’t walk around the street asking ordinary people gotcha questions to make fun of their dumb answers like Leno or Kimmel (who’s recently pulled even with Leno among the advertiser-coveted 18-to-49 demographic, which goes a long way toward explaining Fallon’s seemingly sudden move to 11:35). He doesn’t try to expose his guests’ hypocrisy like Stewart or Colbert. In contrast to Letterman, he actually watches his guests’ movies, listens to their music, and geeks out endearingly in front of them. (Some find that adoration borderline obsequious, but it makes him a more natural successor to Leno than Conan O’Brien ever was.) Colbert is probably his closest equivalent as far as acting chops, but he never breaks character. Fallon will, and does, play anyone, five or six characters in a single show, with a we’re-just-kids-in-a-costume-room giddiness that’s appealing not just to his audience. It’s appealing to his guests, too, for whom he makes fame seem like a golden ticket to one big bouncy castle. Sure, Justin Timberlake is a ham, and probably could have been persuaded by some other host to perform a running ­History of Rap delivered in karaoke-style installments. But who else could have morphed into seventies Neil Young to perform Willow Smith’s “Whip My Hair” and then gotten Bruce Springsteen, in his own self-mocking Born to Run getup, to join in? (“He does me so well, I don’t have to bother anymore,” Young has said.)

All that versatile silliness may also help explain why Fallon’s Late Night monologues have tended to underperform his other segments, and maybe why he seems to love it when they clunk spectacularly—like when he threw out that obscure reference to B.J. and the Bear, a late-seventies TV show about a guy driving around the country in a semi with his pet chimpanzee, or when Higgins mentioned Mavis Beacon, a typing program no one remembers from when PCs first came out. “God, that made me laugh,” says Fallon later. “No one got it, not even crickets. Crickets were like, ‘What?!’ ”

Eventually, the Roots at least will always start laughing. “They wanna see me squirm,” he says. “I love that stuff; you can’t write that. It’s off-the-cuff and loose, and it should be loose. We should be able to bomb and be able to just be free and joke around.”

Back in the studio, the circumcision bomb is turning atomic. “There will be no monologue at all!” Fallon shouts. “Throw it in the garbage!”

“Throw it in the trash!” says Higgins.

“Throw it in the dustbin!” says Fallon.

This has to end. Higgins gives Fallon a lifeline: “Just Riverdance.”

Fallon springs into action, hoofing with the determination of a man who knows only he can stop the monologue from completely blowing up. The studio roars. Fallon beams. Just like that, he’s gotten them back. Welcome to the future of the Tonight Show.

Not since Johnny Carson decamped for Burbank in 1972 has the ­entertainment-industrial complex’s flagship TV circus been beamed out to the American provinces from its original home in New York City. Whether or not this signals a true shift in cultural capital back to the East Coast, The Tonight Show Starring Jimmy Fallon simply couldn’t be shot in Los Angeles because Jimmy Fallon just isn’t Jimmy Fallon without New York. He was born in Bay Ridge, grew up blue ­collar and Irish Catholic in the rural town of Saugerties in upstate New York, and went to college in Albany. “I never even left the state!” Fallon says, laughing, when we meet after the show. “I’m obsessed!”

Conan O’Brien had dutifully moved out to Los Angeles after (briefly) unseating Jay Leno in 2009, but when NBC approached Fallon about The Tonight Show, he took a different tack. “I didn’t insist,” he says. “I just kind of hinted at it and said, ‘It would be great if we could bring The Tonight Show back to New York.’ And then there was kind of like a silence on the other end of the phone.” Even once the deal was made, Fallon kept it a secret from the staff until the press release went out in the middle of a creative meeting. “Everyone’s phone starts buzzing at the table. Zzzzzztttt. Zzzzttt zzzzttttt zzzzztttt. And I’m like”—he shrugs—“and people are like, ‘Holy crap, man! What?!’ It was like The Wolf of Wall Street, everyone’s barging in the office like, ‘What’s going on???,’ hugging, crying, people were dancing. Everyone could stay in New York. Their families, their kids in school, they can keep their apartments. It was emotional.

“I don’t think L.A. was an option, honestly,” he says. “I really didn’t want to go to L.A. It just doesn’t fit me, you know? I love this city, and when I think of nighttime, I think of more New York than I do L.A. I always think of L.A. as, like, sunshine and palm trees and healthy people.”

“Healthy” is not an adjective that would have described Fallon during SNL. “Everyone in New York has a Jimmy Fallon story,” says Seth Herzog, his good friend and Late Night’s warm-up comic. “It’s always like, ‘In 2000, Jimmy threw this dude out of a bar, or poured his beer on someone, or got on a table and sang a song.’ ” Jonah Hill, a guest the night of the circumcision joke, used to spot him at Black & White in the East Village, when Hill was a New School student reading absurdist plays he’d written on open-mike nights. A friend of mine recalls Fallon spending an entire happy-drunk night hanging out with her and her friends at Siberia, a now-defunct underground dive bar in the 50th Street subway station. For months afterward, she kept running into him on the street, in the East Village, in Gramercy Park. “He remembered me every time,” she says.

“Siberia, that was magic! The best dive bar I’ve ever been to in my whole lifetime, oh my God,” Fallon tells me. “I really put some time into that bar. I put some dents into that one, man. I brought my parents there and everything. I was really proud of it.”

“We were super-functioning alcoholics, definitely,” says Horatio Sanz, Fallon’s SNL cast mate and drinking buddy. “They say that kind of goes hand in hand with SNL, some kind of substance-abuse issues, because it’s so stressful you easily find yourself blowing off steam a lot.” Niagara in the East Village was another favorite; Sanz once demanded a ­margarita in the biggest glass the bar had, which turned out to be a vase, and woke up on the sidewalk in front of his apartment. “Yeah, we got in a couple of brawls,” says Sanz. “I’ve seen Jimmy clock a few people.” Sanz’s favorite fight happened at another haunt, Peter McManus Cafe on 19th Street. Fallon started pouring a beer on someone’s hat, thinking it belonged to Sanz’s friend. “The owner of the hat, we didn’t know who he was, said something like, ‘What the fuck are you guys doing?’ and Jimmy just punched him. He wasn’t that hurt; he just walked into a tornado of drunken stupidity. Yeah, Jimmy could fight. I don’t know where he learned, but he definitely scrapped with the best of them.”

Fallon always figured he’d leave SNL after three seasons, like his idol, John Belushi, but Lorne Michaels offered him “Weekend Update” with Tina Fey, so he stayed on for six, quitting in 2004 to move to Los Angeles to start a movie career. Sanz says that when he saw a three-story Calvin Klein billboard on Houston Street “of Jimmy as a young James Bond, that’s when I knew maybe he was going a little too far.” He signed on for 2004’s big-­budget comedy Taxi, with Queen Latifah, which flopped, and 2005’s Red Sox–themed romantic comedy Fever Pitch with Drew Barrymore, which also flopped. (Though on the bright side, he met Barrymore’s producing partner Nancy Juvonen, who became his wife.) Eventually, he came back to New York and spent a couple of years aimlessly knocking around before Michaels recruited him to take over O’Brien’s Late Night. Every time I’d see him in those years, as a reporter on red carpets and charity galas, he’d shout, “Hey, buddy!” Then he’d chat for at least ten minutes and thank me, explaining that no reporters ever approached him anymore.

“It was rough days! I couldn’t get arrested, man.” And maybe it helps explain why he’s so unburdened by fame now. “It’s a treat, it’s awesome, because I know what it’s like not to be famous. When you experience both sides of it, this side is much better.”

Photo: Martin Schoeller

“Hey, buddy! Hey, buddy!” he greets each of the front-desk receptionists at Golf & Body NYC, a midtown gym he’s just joined, asking one about the Salman Rushdie book she’s reading and the other about Secret Aardvark, a hot sauce made in Portland. Now that he’s graduated to the Tonight Show, “golf is gonna be my thing,” he says, and that night, after taping the Jonah Hill show, he’s invited me along to hit golf balls at a simulated Pebble Beach projected on a movie screen. “I have to be a rich old white guy, that’s what I have to become. It’s so sad, but I gotta play the part, man. I’ve already got my cardigan.”

For a while now, he’s had summer-Friday golf dates in New Jersey with Mario Batali and Michael J. Fox. Now he’s serious enough about improving his game that he’s had clubs fitted for him and is taking weekly lessons with a pro, studying golf books, watching Caddyshack, and doing calisthenics with an exercise ball. “I twerk for about 25 minutes,” he says. “There’s a lot of hip motions—Shakira is probably very good at golf.”

A gym waitress brings over beers and bottled water. “God, this is my favorite water!” Fallon exclaims, then gets slightly embarrassed by his unbridled enthusiasm. “Not like I have a favorite bottled water. But Voss water is so good!”

“Here’s the good news: We both suck,” he says after hitting a crooked drive. “I killed Bambi, I just killed virtual Bambi,” he announces when he hits a ball into the woods. But he knows enough to suggest I try a hybrid iron, which immediately improves my swing. “That’s your club, that’s your club!” Every shot is marked with an exclamation: “Hooya!” “Smack it like it’s your enemy!” “Dude, that’s fantastic!” And when he offers to take a putt for me after my fifth mulligan (“We do a Carey Mulligan, and then it’s like it never happened”), he presents it like I’m doing him a favor by letting him practice. “Oh, that feels good! After 30 shots, we finally got it in the hole. That was just magic.” The next day, he sends me a video of me thwacking the ball, edited to play in slow motion and abruptly clipped so you never see how terrible the shot turned out.

Fallon has never been much of an ­athlete—he joined the golf team in high school because he heard a school announcement saying, “ ‘Uh, hey, if there’s anyone interested in joining the golf team, we need one more player or else we can’t have a team.’ So I was like, Well, so I’ll definitely make this team if I try out.” His greatest sports triumph came at a tournament where the fate of the team relied on his sinking an impossible putt. “Sun’s setting, it’s quiet, everyone’s watching, pressure’s on,” he says. “Oh my God, it was crazy. I go”—he pretends to putt and clicks his tongue—“and I’m just watching it, it’s so slow motion, and it fell into the hole, and we won, and everyone’s like Whaat!? If there is a Rocky of golf moments—it was so awesome I’ll never forget that. You’d think hole-in-one is people’s dream. For me, it was just finishing and not being a loser.” He also once slam-dunked in a pickup game at an Albany court called Shit-Talkers Park, he says. “The place went bonkers. Even the other team was laughing. It was like White Men Can’t Jump. I mean, really, I actually can’t jump; it was a pulled-down rim. I’ll be able to tell my kids about that.”

His lack of athleticism was recently on display, he says, when he dressed up like a bandanna-headband-and-denim-vest-wearing eighties Springsteen, alongside actual Springsteen in matching costume, to sing a song about New Jersey governor Chris Christie’s Fort Lee traffic-jam ­scandal. “I forgot that I’m gonna be sleeveless, and I’m looking at my arms and I’m like, I gotta do something. And so I start doing push-ups in my dressing room, and he walks by and”—Fallon breaks into his Springsteen imitation—“ ‘No fair! That’s cheatin’!’ So he comes in and starts doing push-ups. So we’re both dressed like him from 1984, doing push-ups, trying to get our arms big. I wanna say I did, like, 40 push-ups. He did probably 60, easy. I’m seriously out of breath. I mean, dude, he’s 64 years old and he’s got guns! And I just look like a pale, doughy version of Bruce Springsteen.”

Outside Golf & Body, Jimmy ­Fallon’s Town Car awaits. He spends his commutes brainstorming paraphernalia with the new full-moon Tonight Show logo (“A Moon Pie would be genius, right?”) and other assorted inventions (invidually wrapped cranberry slices, “The Love Coaster,” a connected double coaster meant as a pickup aid: “Hey, can I share your coaster?”).

“What’s up, Harold?” he greets his driver, before helping me over a snowdrift and running into traffic to get into the far door. “Growing up, man, things have changed,” he says, patting a leather seat. “Remember the old me who used to stumble out of bars? I cruise around in, like, BMWs now.” He’s also switched from jeans to slacks. “I guess I really am becoming a dad, right?” Now 39, he actually is a dad; he and Juvonen have a 6-month-old daughter, Winnie, delivered via a ­surrogate after five years of struggling to conceive. His days of being the SNL heartthrob who dated Parker Posey and Winona Ryder are long gone. “Lena ­Dunham was saying, ‘Dude, when you were on SNL, you were like my high-school crush,’ ” he says. “ ‘What do you mean I was your crush?’ She’s like, ‘Nah. Sorry, the fire’s not there anymore.’ It’s like, all right. I don’t mind being a grown-up. I’m not the boy-band guy anymore.”

Fallon was 17 when Johnny Carson retired at age 66 in 1992, and he seems less reverential of that legacy than, say, Leno and Letterman, who personally owe their breaks to Carson, and Kimmel, who grew up idolizing Carson by way of idolizing Letterman. “Johnny Carson was just the guy who was on every night. It’s almost like he came with my TV set,” says Fallon. “When I was a kid, I didn’t know that I could dream about taking over for Johnny Carson. I didn’t know that he’d retire. I didn’t know what that word meant.” SNL was always his pipe dream—if he didn’t go into computer science and work at IBM like his dad. But he did tape Carson’s last week of good-bye shows and Jay Leno’s first show, he says, “thinking that I would be the only guy, like, the historian that had the copy of Jay Leno’s first show.”

It wasn’t until he got his own talk show that Fallon started visiting the Paley ­Center for Media and watching old tapes of Carson, Jack Paar, Steve Allen, and Dick Cavett. “The best was The Larry Sanders Show,” he says. “Garry Shandling’s fake talk-show character taught me a lot.” That show was how he got a sense of what it was like to do the job. “It’s like, guests drop out or a piece doesn’t work. It’s just interoffice drama on top of everything; it’s actually a lot of managing, a lot more than I thought it would be. It’s more than just hosting a talk show.”

Fallon says he and Leno talk every couple of weeks—“We’re as close as we can be without being friends. I mean, I don’t have dinner with him”—and that it was Leno who called him to say, “I think next year might be my last year” and give Fallon his blessing. He says he asked Leno if he’d like him to host an hourlong tribute to him (Leno said no), and that he solicited Leno’s advice for what to change to make the show Tonight Show–ready. “He said, ‘You should make your monologue longer,’ ” says Fallon. So back in August, Fallon and his writers tripled the jokes, from around three minutes’ worth to eight to ten, sometimes fifteen, with graphics and sketches thrown in. Leno’s gracious guidance might be a little hard to believe, given Leno’s (polite) recent exit interviews, where he’s said of retirement, “It’s not my decision.” But, Fallon says, “He was really, really sweet to me. He said, ‘I think you’re the closest thing to Johnny who’s in this different generation.’ ” (As for whether NBC will be more patient with Fallon’s show than O’Brien’s, he’s relying on his gut: “They haven’t actually given me, like, anything in writing. I’m just assuming it’s gonna work, so maybe I’m dumb for that.”)

Fallon seems to understand that the job of a late-night host is no longer putting the nation to bed (he even bought his parents a DVR and programmed it himself, so they can watch him in the morning). So what does he see as the goal of that job, which only five other people have had? Simply making people laugh (“so you live a longer life”). “I’ll do whatever it takes. If you want me to sing, I’ll sing. You want me to dance, I’ll dance. You want me to dress as a woman, I’ll dress like a woman. I don’t care what I have to do. But I never do anything sneaky or try to make guests look bad or try to trick them.” It’s a blurry line between hospitality and becoming a human promotional machine, but when Fallon has guests play any number of modified parlor and collegiate bar games (Catchphrase, flip cup, double-turtleneck Ping-Pong) it’s because he’s genuinely interested in how they’ll behave and in showing that side of celebrity. “Like, how is Julianna Margulies if you play Pictionary with her? Does she freak out? I mean, is she cool? Is she competitive?” He swears he genuinely wants the world to see Michelle Dockery from Downton Abbey happily running around trying to catch rings with a helmet made of deer antlers and Tom Cruise being a good sport while smashing two raw eggs on his own forehead in a game of “Egg Russian ­Roulette,” and big scary action star Jason Statham giggling and laughing like a kid while he and Fallon throw water in each other’s faces while playing the card game War. And, really, how can you doubt him?

“It’s secret, right? How rad is this?” Fallon asks me excitedly. We’ve arrived at Turntable Mad for Chicken, a Korean wings joint on a desolate stretch of Fifth Avenue in the lower Thirties, located upstairs through an unmarked door between a pizzeria and a Chinese takeout place. It’s not his No. 1 Korean chicken spot—that would be KyoChon—but it’s a close second. “You’re gonna freak out,” he says. “The wings are the jam.” And he likes the fact that there’s a D.J. booth no one uses, and that beer is served in pitchers with flashing lights and smoke from dry ice coming out of them. “I should get one of these, right?” he says, pouring us glasses of Asahi. “Anytime you can make it look like a science experiment, that’s just perfect for me. Cheers!”

We’re seated in an alcove right next to a blaring speaker. I discover later that when I leave to ask if the music can be turned down, Fallon’s been narrating into my recorder: “It’s hilarious that ‘Shout’ is on because that’s literally what we’re doing, shouting. It’s like we’re crashing someone’s wedding. I’m gonna start doing the chicken dance and the electric slide.” To the people seated nearby, it must’ve looked like he was talking to himself.

He’s in the middle of telling me how he still loves drinking but can’t do it as much as he used to, what with his metabolism slowing down and the baby and the daily responsibilities of having a talk show, when the other table in our alcove sends over a “peach bomb,” basically a hangover in a glass. It’s Frankie’s birthday, they explain. Who? A very drunk young Asian kid raises his glass. “It’s his birthday, so I have to get drunk?” Fallon shouts, laughing. “I don’t understand the rules! All right. When in Rome.” He drops a shot glass of vodka into the sickly sweet orange-­colored syrup and chugs. “It’s been a while. I’m back!” he says, slamming the glass down and shaking his head. “Frankie’s birthday. I’ll never forget this day. Especially tomorrow. Really, not gonna forget it tomorrow.”

It’s getting close to midnight, and the waiter comes over to ask how things are. “Beyond good,” Fallon tells him. “This is the best. I mean, the soy wings are delicious, the hot wings are unbelievable, the kimchee is off the charts.” Everything is going so well he can barely believe it—which goes for the preparations for the show, too. “I just want a beautiful TV studio, and that’s what we got. It’s gorgeous,” he says. “Questlove’s like, ‘I’ve never been in a studio this tight—it’s airtight!’ ” He’s announced the bookings for his first show — Will Smith and U2 —and nearly ended his Late Night tenure in a bubble bath with Barbara Walters. She agreed, but ABC put the kibosh on it.

“Are you the guy from Taxi?” a fan approaches. “Great movie. What have you been up to?” Fallon shakes the guy’s hand and tells him he’s working hard on Taxi 2. A second fan thanks Fallon: He sent a girl a link to Fallon’s Game of Thrones parody, “Game of Desks,” and got a date because she thought the link was funny. “Awesome; one awkward date at a time,” says Fallon. “Good luck with it.”

“See,” says Fallon when he sits back down. “In L.A. you wouldn’t get those two drunk people coming up to me.” He’s gotten everything he wished for, but he knows that it’ll come with intense scrutiny. “I mean, I’m sure we’ll do great the first week because the Olympics will give us a good lead-in,” he says. “And then after the Olympics, you know, we have a normal ten-o’clock lead-in, so the ratings will go down. That’ll be a headline: ‘Fallon loses 40 percent of his audience.’ ” Then, outgoing SNL head writer Seth Meyers will take over Late Night, “so our ratings will go up a little bit because people will be intrigued about Seth’s show, and then after that week, it’ll go back down. And that’ll be kind of where we can start building from there.” He stops abruptly and springs to his feet. “Let me hop in this.”

I turn around to see him jump into a group photo at Frankie’s birthday table. There’s a cacophony of surprised, overjoyed screaming. Fallon’s making rock-star grimaces and heavy-metal horns with his hands. “That was awesome!!!” a girl shrieks. Fallon slinks back to our table with a huge grin on his face. “I’m sorry,” he says, “but that was so good.”

*This article originally appeared in the February 10, 2014 issue of New York Magazine.

Styling by Susan Winget; Styling consulting by Stephanie Biear; Prop styling by Bednark Studio; Hair by Courtney Benedetti for Oscar Blandi at Tracey Mattingly; Makeup by Cyndie Boehm for La Mer at Tracey Mattingly; Suit by Saint Laurent; Shirt by Brooks Brothers; Tie by Giorgio Armani from Saks Fifth Avenue; Belt by Gucci.

Photos: Martin Schoeler; Martin Schoeler; Martin Schoeler