Toward the end of February, in the first-class cabin of a United flight from Hawaii to Los Angeles, the only man on the planet who has hosted late-night talk shows, appeared on late-night talk shows, and created an iconic TV series that parodied a late-night talk show encountered the man who had just been famously ousted from a late-night talk show.

Garry Shandling was in 1A. Conan O'Brien and his family were three rows back. The two men are close friends, and their unexpected proximity made Shandling happy—so happy, he says, that he asked a flight attendant to deliver O'Brien a present. "Mr. Shandling can't finish his cookie, and he thought you might want to have the rest," the woman told O'Brien, presenting the crumb-littered plate. Minutes later, Shandling looked up—way up—to see the six-foot-four-inch redhead planted in front of him, an exaggerated scowl on his face.

"This is the way you treat me, with the broken cookies?" O'Brien asked Shandling, his voice slightly raised to make sure the comedy could be heard over the jet engines. "When I let you get in line with me and my wife and get your ticket ten minutes earlier? This is what you do?"

"Let me see if I understand this correctly," Shandling responded, almost yelling. "I, out of the generosity of my heart, offer you food. And you have the nerve to walk up to my aisle and harass me and heckle me in front of this passenger"—Shandling nodded to the stranger in 1B—"who I don't know?"

O'Brien turned to Shandling's stunned neighbor, who will surely be dining out on this story for the rest of his life. "I'm sorry you have to sit next to him," O'Brien said. "You know, if you call ahead and you find out Garry's on the plane, they will allow you to switch seats."

It was a coincidence, these two funnymen being on the Big Island at the same time. Shandling, who had recently completed final reshoots on his first acting role in years—a U.S. senator in Iron Man 2—was enjoying one of his frequent retreats to the Waipio Valley, his favorite place to meditate and ponder the universe. (While he stops short of calling himself a Buddhist, he is a serious student of dharma.) O'Brien, who just weeks before had parted ways with NBC and The Tonight Show, was on what is perhaps best described as a forced vacation. The timing was "synchronistic," Garry says, recalling that they hung out so much in Hawaii "that Conan's wife was jealous."

"We were able to spend some time chatting about, uh, the turtles and anything else that might be going on in our lives," Shandling says as we stand in the kitchen of the vast Spanish-style home where he lives, alone, in the hills above the West Los Angeles enclave of Brentwood. You can see the distant ocean out the window, past a grassy oasis and Garry's rock-lined pool. He looks tan and fit, if a little rumpled, in an untucked striped button-down, baggy cargo pants with a tiger emblazoned on one leg, and beige Prada sneakers. When I press, he acknowledges that yes, the topic of O'Brien's future came up. "Conan's completely free now," Garry says with a solemnity more gurulike than you'd expect from someone who got famous making jokes about his hair. "He doesn't have to fit into someone else's mold."

But what Garry really wants to talk about is that hand-me-down cookie. "I'd eaten half, and the other half was in tiny crumbles and pieces," he says, still delighted. Asked what kind of cookie—oatmeal? chocolate chip?—he adjusts his black baseball cap and takes off: "I asked the same question, and they said, 'It's an airplane cookie.' And I didn't want to ask what that was exactly. I was frightened." A beat. "I was in a situation once over water where they said they were having a technical problem with my cookie. I said, 'Oh, my God, what are you going to do?' They said, 'We're going to have to switch cookies. Give us ten minutes.'"

He's not merely riffing. It turns out that the man who is widely credited with redefining the sitcom, introducing self-referential humor to the masses, and paving the way for Seinfeld, The Office, and Curb Your Enthusiasm, has been working hard on something new.

"I have this very abstract idea in my head," he confides. "I wouldn't even want to call it stand-up, because stand-up conjures in one's mind a comedian with a microphone standing onstage under a spotlight telling jokes to an audience." That kind of comedy is fine, he says, but for him it's in the past. Shandling is striving to exist—and thus to be funny—completely in the moment. "The direction I'm going in is eventually you won't know if it's a joke or not," he explains, describing his new act, which he has been quietly testing in clubs where his name never appears on the marquee. "What I want to happen is that I talk for an hour and the audience doesn't realize it is funny until they're driving home."

BASKETBALL

Every Sunday he's in Los Angeles, Shandling calls the game for noon. The invitation-only crowd gathers in his kitchen to drink coffee, and at twelve thirty everyone heads out the patio doors, past the pool, and down a series of steps into the lower yard. As is the custom, the first person to reach the half-court grabs a leaf blower and sweeps it clean. Then they play: three-on-three to seven points, win by two. When only the regulars show—they include Sarah Silverman, Kevin Nealon, David Duchovny, and Friday Night Lights creator Peter Berg—no one sits out for long. Other times, you're lucky to get on the court. Sacha Baron Cohen and Adam Sandler have played, as have Ben Stiller and Billy Crystal. Judd Apatow plays infrequently, but only, he says, because "Sarah's better than me, and it's shameful for me, as a man, to accept that."

The sweat, the speed, the lack of pretense—it gets sort of elemental. "It's stripped-down," says Peter Tolan, one of Garry's best friends and a former chief writer on The Larry Sanders Show, Shandling's pioneering metacomedy on HBO. "People show themselves truthfully in a time of competition, and that's what he's interested in." After a few hours, Shandling leads everyone up to the house to eat takeout and watch sports on TV. There is no agenda at Camp Garry, as Silverman calls it. But it's not a party—Shandling is adamant about that. Instead, it's something of an incubator. Aficionados of Sanders may recall an episode in which Duchovny, playing himself, admits to having sexual feelings for Sanders. That's just one moment of TV genius that was hatched on Shandling's court.

"I was guarding him," Duchovny recalls, "and you know, my pelvis was near his rear end, which happens sometimes when you're guarding a man. And I said, 'It would be funny if I had a crush on you but I was straight. I don't know what that means, but that seems like it would be funny.' And Garry said, 'Yeah. Yeah. Your instincts are good.' Garry's always talking about your instincts."