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.
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