Here's Jimmy Kimmel

Smoking weed, sleeping over and stalking Jay Leno: At home and on the prowl with the man who would be king of late night

jimmy kimmel 1174
Mark Seliger
Jimmy Kimmel on the cover of Rolling Stone.
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In 24 hours, Jimmy Kimmel will stand up in his office at the El Capitan Theatre in Hollywood, looking less like a talk-show host and more, to use his words, like "a hobo." He'll be wearing baggy mesh Dodgers shorts, a rumpled old Coca-Cola T-shirt and no shoes; his hair will stick out in three directions. As he leaves his desk, where he's been refining jokes since the morning, his transformation into late-night star will begin. After a quick haircut, he'll carry his MacBook to the makeup room, where he'll put the finishing touches on his monologue while a woman named Stephanie puts the finishing touches on his face: powdering his skin, shaping his eyebrows, blackening his hair where it's a bit too gray or a bit too thin for HD. In his private bathroom, he'll change into a crisp white shirt, a colorful Prada tie and slim blue Gucci pants. His wardrobe guy will bring the matching jacket, steamed and lint-rolled and bearing a sticker on its lining that says ABC ASSET above a bar code marking it as network property. "I've got the same bar code tattooed on me," Kimmel will joke. "It used to say ABC LIABILITY, but they changed it when the ratings got good." As he makes his way downstairs – where a 200-strong crowd is waiting for that night's episode of Jimmy Kimmel Live! to start – a group of writers, producers and crew will fist-bump Kimmel and chant, as they do before every episode, "Best show ever! Best show ever!" His band will launch into an ecstatic fanfare and Kimmel will stroll out, hit his electrical-taped mark, and fix his eyes on the teleprompter as the audience roars its welcome: showtime.

But that's not for 24 hours. Right now it's Sunday night, Kimmel is at his beach house, and he wants to get high. "If we smoke weed right now," he asks, "is that on the record?"

Kimmel is sitting at a weathered wooden table in his dining room. Blinky and unshaven, hair tousled, he looks like he just woke up from a phenomenal nap. Kimmel's fiancee, Live! co-head writer Molly McNearney, is in the kitchen, drinking fruit punch and tapping on her phone. "I don't know if I want this in the story," Kimmel, 45, says, padding off to retrieve his stash. "My kids are gonna read this. . . ." He returns with a vacuum-sealed baggie bulging with buds the size of baby Brussels sprouts.

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"We know people with dispensary cards," McNearney, 34, says, referring to California's medical-marijuana storefronts. "Jimmy doesn't want to be seen coming out of one of those." Tall and athletic, with dirty-blond hair and a sly smile, McNearney has been romantically involved with Kimmel for three years, and she's worked on his show almost since its 2003 debut. The couple just got back from spending Thanksgiving with McNearney's family in St. Louis, and Kimmel is trying to enjoy the final hours of the long weekend. The holiday wasn't entirely relaxing. Kimmel's an exacting foodie, and when he discovered that McNearney's mother planned to cook a pasta dinner on Friday using jumbo jars of Ragu, he sprang into action, shopping for fresh ingredients and whipping up emergency penne for 30. "I could not let that happen," he says.

Kimmel spends most nights at a vast, ultramodern home he owns in the Hollywood Hills, but he bought this place, an unassuming four-bedroom in Hermosa Beach, in 2004, for weekends. "I like a real beach," he says. "A crowded one, you know? People, towels, umbrellas. I hate those little private strips of sand you see up in Malibu."

The walls and bookshelves are lined with family photos, including several of Kimmel's daughter, Katie, 21, who's in art school, and his son, Kevin, 19, who's studying filmmaking. In one corner, there's a black-and-white picture of 5508 Tilden Avenue, in Brooklyn, where Kimmel was born and where he lived until the age of nine, when his family moved to Las Vegas.

As Kimmel packs pot into a ceramic one-hitter, he offers me a three-word disclaimer regarding its potency – "This is California" – before going on to puff deeply and repeatedly. McNearney abstains, munching some trail mix and grinning. "You can't smoke in front of a reporter and say it's off the record," she tells Kimmel. His head is cocooned in fumes. His eyes, always heavily lidded, narrow even further as he savors the weed and considers McNearney's point.

Ten years ago, Kimmel wouldn't have thought twice about getting high in an interview. In 2002 – fresh from his runaway success as the co-host and co-creator, with his friend Adam Carolla, of the idiotically inspired beer-bros-and-boobies revue The Man Show – ABC picked Kimmel over Jon Stewart to anchor a freshly created 12:05 a.m. comedy vehicle. Kimmel was pitched as an irreverent new breed of host, poised to shake up a staid late-night landscape with his man-child wit and proven appeal with men ages 18-34. In the first two seasons of Jimmy Kimmel Live!, which had its debut in January 2003 (and which hasn't actually been live since the first season), Kimmel played the convivial boor crashing the late-show party. He foreswore the standard-issue necktie, scrapped the time-honored opening stand-up segment and served free booze to his audience. His thumb-nosing sensibility was on proud display: filling the show with man-on-the-street pranks, insulting Oprah constantly, hiring Mike Tyson to co-host for a week.

But despite flashes of zany brilliance, the show struggled in the ratings. "I was hired to get male viewers," Kimmel says. "But almost overnight, ABC became a very female network – I think Grey's Anatomy started it – which meant I was suddenly very out of place. So I had to change. I had to dull some of the edges – try to limit the number of times I say the word 'penis' to four times a show instead of eight."

Over the following decade, Live! – and Kimmel – changed. He grew to respect convention more: Hello, neckties and monologues. "If you want to do a talk show on network television, you're probably going to wind up having a desk and a band, wearing a suit and having a sidekick," he says. "Audiences want to feel comfortable." (Kimmel's Sancho Panza is Guillermo Rodriguez, a former parking-lot security guard with an exquisitely unstudied comedic gift.) Kimmel dieted, going from a schlubby 210 to a trimmer 190. He downplayed the more aggressive, acid persona he'd cultivated on The Man Show and Crank Yankers (a frequently brutal prank-call show he co-created) and began showcasing softer sides of himself, like his easy rapport with children. "Instead of a caricature," he says today, "I'm a person." By 2012, he'd had Oprah on as a guest and engaged in a "nice-off" with Ellen DeGeneres, battling to see who could out-compliment whom (Kimmel lost, but it was close).

The culmination of Kimmel's decade-long evolution arrives this month: On January 8th, ABC is moving Jimmy Kimmel Live! forward to 11:35 p.m., putting him in direct competition with Jay Leno and David Letterman. This milestone comes after a smash 2012. There was the White House Correspondents' Dinner, which Kimmel hosted in April, getting big laughs by making fun of Rush Limbaugh ("that slut"), Kim Kardashian ("the greatest threat to America today") and, for the policy wonks, Peter Orszag; President Obama gave Kimmel a high-five at the end. There were the Emmys, which Kimmel hosted in September, where he punked the format in novel ways like running an "In Memoriam" segment set to stirring Josh Groban­accompaniment and devoted entirely to clips of Kimmel himself. And during the 2011-2012 season, the Live! audience increased by three percent, making it the only late-night talk show to post a year-to-year increase. In terms of weekly ratings, Kimmel has beaten Leno once and Letterman twice with coveted 18- to 49-year-olds, and Jimmy Fallon – who doesn't go on till 12:30, but is seen as Kimmel's closest counterpart – over and over.

For Kimmel, ever-broader success comes with built-in tensions. What's been consistent throughout his career is a winningly unaffected everydude appeal. "He's not show business; he's not Hollywood," says Michael Davies, a former ABC executive who helped get Kimmel the late-show gig. "He's a much more raw, blue-collar guy than has ever sat in that seat and done that show." Jill Leiderman, a Live! executive producer who used to work for Letterman, says that "as a viewer, watching Late Show, you aspire to be Dave's friend: He seems untouchable, like a king," but "watching JKL, you feel as if you already are Jimmy's friend." That sort of relatable, down-to-earth aura becomes harder to maintain, though, when you command an annual salary reported at $6 million, and when a network bets big on you, as ABC is doing with Kimmel's new time slot: The stakes rise precipitously in terms of your public image, to the point that you might worry about, say, getting stoned out of your brain with a magazine writer.

"Ah, fuck it," Kimmel says, passing me the one-hitter, grabbing two shot glasses and uncorking a jug of corn whiskey his friend made. "Write about the weed."

With the sun slipping behind the Pacific, Kimmel suggests that the two of us take a walk. At first he doesn't seem high – he's speaking animatedly, in precise sentences – but halfway into a story about attending a mixed-martial­arts bout with his pal Dax Shepard, he chuckles and says, "What was I just talking about?" He apologizes: "I haven't smoked weed in, like, a week." We tromp onto the sand and curve back to the street, where three guys on beach cruisers roll by, looking tough. "Some of the dudes around here are hard," Kimmel says. "They will slash your throat with a fucking toenail."

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Back at the house we decide on Mexican for dinner. Food is Kimmel's obsession. He has numerous celebrity buddies – Matt Damon and Ben Affleck (who both make frequent appearances in comedy videos on Live!), Howard Stern, John Krasinski – but the names he drops most frequently are those of chefs he's befriended: Italian don Mario Batali, pizza savant Chris Bianco, BBQ hero Adam Perry Lang. On the patio at Kimmel's Hollywood home, near a fire pit, pool and miniature waterfall, he's installed a Renato pizza oven. It sits beside a smoker, a Viking grill, a tandoor oven and a paella grill. Kimmel grows fresh herbs in little white tubs, and he makes his own vinegar. He recently bought the house next door and knocked it down, intending to build a little farm and raise chickens.

Before we leave, Kimmel puts his weed baggie into a sous-vide-cooking vacuum sealer, locking in the freshness in an impressive display of pothead-gourmand ingenuity. "This way," he says, "it won't stink up the whole house." We get into Kimmel's BMW SUV downstairs. In the back seat is a case of harmonicas, which he likes to play on long drives. "He's good at 'Piano Man,'" McNearney, riding shotgun, says.

On our way to dinner we pass a venue called the Comedy & Magic Club. "Leno's probably here tonight," Kimmel says. "He comes here every Sunday and does a stand-up set." For decades, he explains, Leno has used the club to audition jokes for The Tonight Show. "We'll know he's here if one of his cars is out front," Kimmel says, referencing Leno's storied fleet of classic vehicles. Kimmel slows down, scoping out the scene, but Leno doesn't seem to be here yet. I ask if Leno's sets are any good. "Leno hasn't been a good stand-up in 20 years," he replies.

Since 2010, Kimmel has been a card-carrying member of the Hate Jay Club, a council of talk-show luminaries that famously includes Stern, Letterman and Conan O'Brien. Kimmel's scorn for Leno sprang, initially, from a love of Letterman, who seemed set to inherit Johnny Carson's seat in 1992, when Leno outmaneuvered him: "Remember, he stole The Tonight Show from Dave, his friend," Kimmel says. He watched Letterman's Late Night religiously in the Eighties, on a black-and-white TV in his bedroom. "His show was just so weird and different," Kimmel recalls. "I'd never seen anything like it. I didn't know anyone who had a sense of humor like that."

Kimmel grew up in a big, boisterous Italian-Irish-German family, but he was in certain respects a solitary kid: He'd spend hours writing, drawing and hand-coloring his own superhero comics, losing himself in private, imagined worlds. "I had a lot of girlfriends back then," he says today, deadpanning. Kimmel and his best friend, Cleto Escobedo (now the bandleader on Live!), would play pranks together, forging a sense of humor based on getting the best of others. Their schemes ranged from ring-and-runs to planting explosive cigarettes among Kimmel's aunt's Marlboros to more elaborate plots: Once, Escobedo, pretending to be a woman, initiated a romance over the phone with a man they'd found in the phone book. "It got to the point where we'd set up meets with this guy, then show up to watch him waiting around," Kimmel recalls, chuckling heartily. "Eventually we felt guilty and let him know we were actually teenage boys. Maybe there was some element of sadism there, but I don't think there was anything deeper than that we thought it was funny." (Kimmel remains an inveterate prankster – a few years ago he sent out a Christmas card on behalf of his agent, James Dixon, featuring an oil portrait of Dixon splayed naked on its cover.)

Kimmel was raised Catholic, and he's still religious. ("I don't understand atheism," he says. "I don't know how anyone could be sure there isn't a God.") But when he discovered Late Night, it seemed like he'd discovered another, secret congregation: "I felt like Letterman was doing the show specifically for me," he says. In high school, Kimmel put L8 NITE vanity plates on his Isuzu, turning the car into a rolling billboard for his infatuation. Following in Letterman's footsteps, Kimmel studied broadcasting, first at the University of Nevada, Las Vegas, and then at Arizona State. After school, he had excellent luck landing radio jobs – holding on to them was another story. He was laid off in Phoenix, fired in Seattle and Tampa, hired in Palm Springs, lured away to Tucson, and fired from there in under a year. The same quality that made him initially attractive to a station, he says, would ultimately lead to his undoing: "They'd tell me they wanted the show to be edgy, but they didn't actually want to get phone calls from people complaining, and from sponsors canceling," he says. He'd mouth off constantly, both in his bosses' offices and on the air, where he'd make off­color remarks and produce scathing parody songs assailing public figures: He got people listening, but he also made people angry. He finally held on to a position doing sports roundups on Los Angeles' behemoth KROQ, which helped him score his breakthrough TV job in 1997, on Comedy Central, co-hosting Win Ben Stein's Money – he was 29 with two kids, earning just "$500 an episode," Kimmel says, but the buzz Ben Stein generated helped him sell Comedy Central on The Man Show, and by the end of its three-season run he was pulling down $40,000 an episode.

When Kimmel first got Live!, he said he intended to do "the comedy version of The Tonight Show," his first major swipe at Leno, who called him for an explanation. Leno and Kimmel hashed it out, and for a few years they enjoyed a friendly relationship. In 2008, as Leno was plotting a jump from NBC to ABC, he started calling Kimmel "three times a week," Kimmel says. Leno intended to do an hourlong ABC show at 11:30, which meant persuading Kimmel to move back a half-hour, to 12:30. "He needed me to be OK with it, because my time slot is written into my contract," Kimmel says. "If they move me out of my slot, I become a free agent – and I had tons of interest from other networks at the time." When Leno's ABC deal evaporated, however, Kimmel says, Leno's calls abruptly ceased, giving the lie to what had seemed like a burgeoning friendship. Kimmel's feelings were hurt. "That made me feel stupid," he says.

Kimmel got his revenge in 2010, after NBC announced it was restoring Leno, who'd failed at 10 p.m., to 11:35, effectively taking back the keys to The Tonight Show from O'Brien. That January, Kimmel hosted an episode of Live! imitating Leno, wearing a fake gray bouffant and prosthetic chin and issuing high-pitched, rimshot-punctuated groaner after groaner. "As a comedian, you can't not have disdain for what he's done: He totally sold out," Kimmel says today. "He was a master chef who opened a Burger King." Leno called Kimmel the day after, saying, sportingly, that he'd enjoyed the impression, and inviting Kimmel onto his show for a satellite interview. When he learned that Leno planned a milquetoast Q&A rather than a discussion of the Conan fracas, Kimmel decided to turn the segment into a blitz. After Leno asked, "What's the best prank you ever pulled?" Kimmel replied, "I told a guy that five years from now I'm gonna give you my show, and then when the five years came, I gave it to him and then I took it back almost instantly." It was one of several digs at Leno's character; Leno, stung, later described Kimmel's appearance as a "sucker punch."

To those who only knew Kimmel from Live!, it may have been a shock to see his teeth bared and gnashing, out for blood – but to those who know him well, the interview was a flare-up of the caustic streak Kimmel had learned over the years to suppress. Howard Stern, who describes Kimmel as a playful, openhearted "dear friend," says that, offscreen, Kimmel's sense of humor "can be sarcastic and biting and sometimes edgy almost to the point of cruel." On Live!, Kimmel restrains himself with guests he might tear into under other circumstances: pretty faces shilling mediocre projects, Dancing With the Stars rejects that ABC forces him to interview, Mama and Honey Boo-Boo. "I know that he sits there with lines in his head and just bites his tongue, because he'll look like an asshole if he doesn't," McNearney says.

For Kimmel, the attack on Leno was a slingshot salvo against late night's Goliath, but it was also a canny career move: Overnight, he went from sideline-sitter to player in the Tonight Show controversy. "Look, it was just jokes – it's not like I said anything that bad," he says. Still, Kimmel and Leno haven't spoken since that encounter. "He's the one who owes me the phone calls," is how Kimmel sees it. Leno declined to respond publicly to Kimmel for this story; an NBC representative told me that "Jay doesn't necessarily feel he has a feud with Jimmy," and denounced Kimmel's comments as "bullying," "infantile rants" meant to drum up publicity.

In Hermosa Beach, Kimmel finds a parking spot. A car full of kids screaming his name passes, but he doesn't seem to notice. In the restaurant he's friendly – "How ya doin'? How ya doin'?" – and no one bothers him. He orders tacos pescados, devours them, and starts working on McNearney's plate. When we're walking to the car afterward, he glances down toward the Comedy & Magic Club and says, "I wonder if Jay's there yet." Kimmel has invited me to sleep in a guest room at his home in Hollywood, but before we head there, he wants to swing past the club one more time. "We'll do a drive-by," he says.

We loop around in the SUV, decelerating as we pass the club. There's still no sign of Leno. "It's still a little early," Kimmel says, peering intently through the windshield like a gangster looking for someone who crossed him. "He'll be here. . . ."

At nine the next morning, Kimmel and McNearney emerge from their bedroom with laptops tucked under their arms. Kimmel, in the mesh shorts and T-shirt he'll wear most of the day, makes espresso from a wall-mounted Miele machine and sits down at his kitchen table with some yogurt and granola. He cues up videos of Black Friday shopping scuffles from that weekend – surefire comedy gold – and plays them for McNearney, who's eating a banana. She begins her daily news crawl – the Huffington Post, CNN, Drudge Report, BuzzFeed – for possible monologue material and to "make sure our writers didn't miss anything."

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The kitchen is vast and sleek and opens into the living room, where the centerpiece is a flatscreen television the approximate height and length of a stretch Hummer. Contemporary art hangs on the walls – a Banksy graffiti study, Massimo Vitali beach portraits – alongside family photos and art by Kimmel's daughter. (He has been divorced from his kids' mother, whom he married at age 20, and doesn't like discussing publicly, since 2002.) On the second-floor landing is a photo booth, the side of which is covered with snapshots of people who've partied here: family members, Spike Jonze, Johnny Knoxville, Krasinski and Emily Blunt, who is, in one shot, in the early stages of mooning the camera, revealing an abbreviated crescent of Blunt-butt as McNearney guffaws beside her.

Celebrities feel at ease acting ridiculous in Kimmel's company, and their eagerness to act out mirthfully on Live! has become one of the show's hallmarks. In 2008, as a birthday gift for Kimmel, his then-girlfriend, Sarah Silverman (he's always been attracted to funny women, he says), starred in a music video in which she announced to the world that she'd been cheating on him with a movie star. "I'm Fucking Matt Damon" went viral, and it inaugurated a tradition of star-studded Live! bits. Kimmel's response video, "I'm Fucking Ben Affleck," featured Affleck, Brad Pitt, Robin Williams, Cameron Diaz and Harrison Ford. "I owe my life to Jimmy," says Mike Tyson, a frequent guest. "When he let me co-host the show, I was at my worst: I was a pariah, just came out the psycho ward, rehab, still getting high. I bit a nigga ear not too long ago! But Jimmy brought me back. When I'm on his show I'll sing, act goofy: I'm loose with Jimmy. With someone else, I'd be afraid they wanted to exploit me – look at Mike do a gorilla dance. But he's trustworthy, and it's all in good fun."

The Damon bit opened up the A-list floodgates, but not every idea works out. "Last week we were told Brad Pitt wanted to do a bit," Kimmel says, chewing granola. "We came up with a great one for him, where we'd open with footage of people fighting for toys on Black Friday, then have the last guy be Brad Pitt, elbowing people, screaming, 'I got a lotta kids!' His people said they loved it, but then we never heard anything." In crafting bits all but guaranteed to go viral, Kimmel has found a way to keep his show relevant among viewers more accustomed to watching comedy on browsers than televisions, and his YouTube channel boasts 780 million views (Fallon's, by comparison, has 57 million). This bodes well for ABC, which is counting on Kimmel to build a fresher, younger audience than Leno and Letterman and a broader audience than Fallon and O'Brien.

Kimmel and McNearney angle their laptops toward each other, sharing videos and headlines. This is more or less how every workday begins for Kimmel: Blurring the line between domestic life and job life, turning the breakfast table into an extension of the show, making work feel less like a grind and more like hanging out with people he loves. These halves of his life weren't always so well-integrated. When he first got married ("too young," he says), he was forced to grow up in a hurry. The instincts and responsibilities of fatherhood kicked in, and you can read the rowdier excesses of his Man Show persona – doing tequila shots, say, from between women's breasts – as a way for Kimmel to experience some of the wild abandon impossible in his real life. "I think that theory might hold up," Howard Stern says. "I lived out some crazy crap on the air, and I'd hate to speak for Jimmy, but we both got married young and it's something we talk about."

In Kimmel's kitchen, the gears are turning. "We should visit some of these shoppers in the hospital who were injured during Black Friday," he tells McNearney. "Find out what shit they bought."

"'Was it worth it?' They'll totally be back there next year," she replies.

"But they'll be more heavily armed," Kimmel says.

They chuckle, then type together in silence.

By 10:45 a.m., Kimmel is at his office at the El Capitan, walking at a brisk four miles per hour on his treadmill desk. The office is a combination workspace/man cave. There's a photograph of him with Barack Obama on one wall; a portrait of Kimmel that Anna Nicole Smith painted hangs on another. In Kimmel's private bathroom, there is a refrigerator in which he stores sal­mon steaks and bison burgers, ready to be tossed into sous-vide machines he keeps in his kitchenette. His toilet is equipped with a bulky electronic seat that "sprays water on your asshole when you're done," he says.

At 11:14, Kimmel receives an e-mail from his writers totaling 12 pages – ideas for bits. Working up a sweat on the treadmill, Kimmel opens the file and tears through it: He can decide instantly whether a pitch is funny or not, and he deletes material at lightning speed. One writer suggests that Kimmel, discussing Thanksgiving, pull a drumstick from his suit. Delete. Another envisions a pre-taped bit involving Lindsay Lohan driving recklessly after reading bad reviews of Liz & Dick. Delete. Another proposes a sketch in which Tyson portrays a blaxploitation badass named "Black Friday." Kimmel smirks – it's a keeper.

By the time he's done chopping at 11:36, the file is two and a half pages long. "If you're batting .310 in comedy pitches," he says, "you're Woody Allen." It's fitting that Kimmel uses a treadmill desk – he has a hard time keeping still. "I'm always looking to the next thing," he says. "There are always hurdles, whether it's the White House dinner or hosting charity events or that night's show: Until they're over, I worry, then I move right on to the next thing. It's hard for me to enjoy the moment. I'm just thinking about not failing. It's an anxious way to live, and it makes me feel guilty when I'm relaxing. A friend of mine just took this radioactive iodine pill as part of a cancer treatment, and he has to be isolated for five days – no contact with the world. I told him I'm jealous of him."

Kimmel's friend, sports columnist Bill Simmons, sees a hard-wired ambition. "He's supercompetitive," Simmons says. "He's not the kind of guy who'd go to the Bahamas and reflect on how great the year was. That's why having a late show, five nights a week, is perfect: He's like an NBA athlete playing a season that never ends. There's no title. You just keep going."

For the past four years, Kimmel's been seeing a therapist, but even here his mania for time efficiency rears its head: He recently persuaded the therapist, located far off in Santa Monica, to conduct sessions over Skype to save Kimmel the commute. "I have to make a point of not bringing my laptop when we Skype, because I'll sneak peeks at my e-mail," he says.

Kimmel spends the rest of the day at Live! weighing in on decisions large and microscopic: giving notes on pre-taped bits, approving font colors that appear onscreen for just a few seconds. Danny Ricker, a writer on Live!, says that "every little thing goes through Jimmy first."

Kimmel concedes that his attention to detail can verge on overkill. "I try hard not to repeat myself and not to do material other people are doing," he says. "We transcribe every other late-night show to make sure there's no similarity. There's no doubt in my mind that we're the only ones who do that, because I don't think other people care that much. And they're probably smarter not to, because you'd really have to pay attention to notice. But I notice."

Many comedians of Kimmel's generation – tortured types with miserable childhoods – want to escape their families. Kimmel, by contrast, surrounds himself with relatives. In a way, they're his secret weapon. At Live!, his brother Jonathan is a director; cousin Sal Iacono is a writer and onscreen foil; cousin Micki Potenza is a fount of funny malapropisms; Aunt Chippy is a foulmouthed regular; Uncle Frank, a retired Brooklyn beat cop, figured into numerous bits before his death from cancer in 2011. "It goes back to our grandfather," says Iacono. "We learned from him – he'd make his watch go off during the middle of weddings, or pretend to be drowning, then spit water in our dad's face when he tried to save him. If you could get a rise out of him, you knew you'd done something good."

All the Kimmels, Iaconos and Potenzas on Live! bring out the best in Jimmy, sometimes with powerful results. When Uncle Frank died, Kimmel devoted a whole show to eulogizing him, eyes tearing and voice cracking. As with Kimmel's assault on Leno, the tribute to Frank was a deeply felt moment that doubled as great TV. "It's embarrassing to me," Kimmel says. "In my ideal version, I'd have medicated myself and I wouldn't have cried."

The biggest example yet of Kimmel's desire to combine work and family comes in July, when he intends to marry McNearney. "The thought of dating my boss was terrifying," she says. "People here know how I've worked my ass off, but I was concerned about what the outside world would think." McNearney plans to leave Live! sooner than later, she says, to develop projects of her own. "When I told Jimmy that," she recalls, "the first thing he said was, 'What about our vacation schedules?'"

After the taping's done, Kimmel returns to his home office, where he shows me an old trunk filled with childhood memorabilia: superhero comics he drew; a signed 8-by-10 glossy of Letterman made out to "Jimmy 'Mr. Sperm' Kimmel." "That's not an authentic autograph – my friend made that for me," Kimmel clarifies. "David Letterman did not call me Mr. Sperm." Moving to 11:35, of course, Kimmel will be up against his hero – a showdown he enters with white flag flapping. "If I beat David Letterman in the ratings, does that mean I'm better than Letterman?" he asks. "No fucking way." In October, in a broadcast from Brooklyn, Letterman appeared as a guest on Live!, offering Kimmel his blessing: "I think you're going to be perfect," he said. After the taping, Kimmel went to his hotel room but was still anxious about the segment. "I was so nervous, I needed something to take my mind off it," he says. "So I got in bed, I masturbated, and then I watched it. It looked pretty good."

Even though the Live! broadcast will now end as Fallon's Late Night begins, Kimmel says he's still watching Fallon closely: "People are going to compare me and him for years to come – we're being positioned as the Leno and Letterman of the next round. I like it, because he's a very worthy competitor. We exchange e-mails. He'll say, 'That was great, I wish we'd done that,' and I'll say similar things to him."

He goes on: "Fallon has more fun on the air. He just seems thrilled to be there, and it comes through. As far as the basics of hosting a talk show, I think I do a better job. He's not that comfortable doing a monologue or a straight interview yet. But he's better at it than I was three years in."

When Kimmel does feel like he's losing perspective, he can refer back to his adolescent self, developing his comedic worldview one Late Night broadcast at a time. I ask him how often he leaves work feeling happy about that night's episode. "Once or twice a month," he says. "You saw how every night we have that chant before we tape: 'Best show ever.' That's a sarcastic thing that we do, but I always evaluate that statement. Some nights I think, 'There's no chance this is going to be the best show ever. We don't have the guests, we don't have the bits.' " He leans forward, his eyes widening. "But every once in a while I think, 'I have a strong monologue, I have the guests, I've got a great musical act. . . .' " Kimmel grins. "And I go, 'This could be it. This actually could be the best show ever.'"

This story is from the January 17th, 2013 issue of Rolling Stone.

From The Archives Issue 1174: January 17, 2013