IT'S A BIT BEFORE 7:00 P.M. and Jim Norton will soon head downstairs to do a set at the Comedy Cellar in New York. He's supposed to be telling me about his current tour, called The Mouthful of Shame—his first in theaters—but he's distracted by his phone. "Dirty texting," he says, shaking his head. This is his one remaining vice, having given up cigarettes and bad food, and he does not try to hide it. In fact, he talks about it at length, not just with me but in public, all of the time. He once improvised a catchy jingle about how he has two phones—"The Good Boy Phone and the Naughty Boy Phone."

But today, Norton is getting no pleasure out of this dirty texting. Has the thrill of talking openly about his offbeat sexual proclivities for 20 years on the radio—first as a regular contributor to The Opie and Anthony Show on SiriusXM, then as co-host—adversely affected his life? Does he experience lingering regrets? Would he prefer to maybe—just maybe—be a more respectable, normal adult?

"Nah. Nobody really gives a shit. I mean, as much as it's hurt me, it's probably helped my career," he says. "In entertainment you can do almost anything. As long as you're not fucking under-aged people or animals, nobody cares. You know, a drug addiction is acceptable in this business. So no, I don't think it's hurt me. It hasn't hurt me, other than the amount of time it eats up. Which is a lot."

Elizabeth Griffin Esquire

We're at the Olive Tree Café—at which comedians performing below eat for free—and he's delicately dabbing the corner of his chicken oh-so-precisely in a cup of mustard. After a while, one realizes it's this kind of rigorous self-discipline that has defined the various contours of his personality, his work, and—because his career is built on analyzing himself and then talking about it—his entire life. So why can't he let go of this last vice?

"It's messed me up, really, just through social networking, talking to women," he says. "They Google you. This one girl I met on an app, we were talking a lot, and she never got back to me when I asked for her number. And I was like, 'Why didn't you get back to me, I thought we were, you know…' And she goes, 'Well, I Googled you and there's some video where you're talking about, you know…' He trails off, but this would-be date could be citing any number of Jim Norton stories: The one about lying on his bathroom floor while an escort defecates into his mouth—he watched the "log" (his word) stand upright for a second before collapsing onto one side on his face. Or the one about a childhood game called "Monster Rain," where he and his friends would go under his deck and jack each other off. Or the one where, in a prostitute's apartment on the East Side, he saw murky water stagnating in the bathtub that gave him such a bad feeling, he paid her and left.

"There are going to be women who are turned off by it. And, you know, I wouldn't mind a relationship now. I don't know if I have anything to offer, I'm so set in my ways. It's really hard to adjust to the idea of another person being there. Sometimes women come over and I'm just like yeaauchh. I blow a load and then I'm like, 'ugh go away.' And I don't want to be like that! It just takes a little adjustment. And if I don't do it now, I don't know if I'm ever going to do it."

And with that, Norton walked downstairs to make people laugh.

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I FIRST MEET UP WITH NORTON nearly 12 hours before, just as the Opie with Jim Norton radio show goes on air at 7:00 a.m. From the moment he woke up that day, he has been on the grind. His typical day begins at his Midtown Manhattan apartment—full of hard-rock memorabilia, baseballs, and boxing gloves all signed and elaborately arranged in glass display cases—and on to the SiriusXM studio where we now are. Later, he'll head to Greenwich Village to spin his latest observations into standup material. Tomorrow, he'll do it again. He's done this 5 days a week for over 10 years.

The first story addressed on this morning's show is David Bowie's recent death. "Would you want to know?" Jim asks Opie and their loyal listeners stuck in traffic across the U.S. and Canada. He's referring to how Bowie reportedly knew of his death and designed his last album around it. "I don't know! I don't think I'd want to know," replies Gregg "Opie" Hughes. Quickly the conversation morphs into politics—"He was 69, and that's pretty old. Like, Tom Coughlin is 70 and people are saying, 'Can he still coach the Giants?' Meanwhile fucking Trump and Hillary Clinton, all of these people are 69, 70..."

Before long, they have a radio program humming.

Elizabeth Griffin Esquire

Norton and Hughes are now the two main nodes of the show, and the reasons it's still considered a radio institution. They are the hosts, and around them swirls an ecosystem whose participants work diligently each day to get this thing on air. An off-hand movie quote sets a producer in motion, Googling the scene, which is then queued up on a flat-screen TV on the wall. Another producer scans the mentions on the show's official Twitter page, which is displayed on another flat-screen. One staffer hovers with a camera and tripod, snapping atmospheric photos that are instantly integrated into various social media presences. It's a well-oiled machine. And it should be; these guys have been doing radio together for nearly two decades.

Norton is perched on his chair, leaning into a puffy mic, as his assistant puts coffee and an egg-white omelet in front of him. At the first commercial break he will devour the food, shoveling it down before they go back on the air; but for now he ignores it. "We're all like, 'Can Coughlin still run the Giants?' But can these people run the country? They're fucking old!"

It's important to fully understand the title of the show, now officially called Opie with Jim Norton. This is the latest iteration of what was once the Opie & Anthony Show. The Anthony is Anthony Cumia, who was fired in 2014 after a racist Twitter tirade against a black woman who had allegedly assaulted him for taking pictures of her in Times Square. (Cumia is white.) The situation was fraught with racial tension, sure—that's what led to his ousting. But it also dredged up professional tension between him and Opie: The two hosts, it turned out, had personal disagreements for years. Norton was like a child stuck in the middle of his parents' separation. It's difficult to this day: "That's such an awkward situation," Norton says. "I refuse to pick sides. I just won't do it. I work with Opie every day, and I'm close to him. He's the guy that got me into radio. But I'm also very close to Anthony. And I will not, in the divorce, say that I'm going to live with one or the other. I just won't do it."

Norton first appeared on Opie & Anthony in the late 90s, tagging along with Andrew Dice Clay. He clicked with the hosts, and was soon their most frequent guest . Once Cumia left, it made sense for Norton to take over. But he's always resisted being called a host, partly because he feels his presence is strongest when he's an outsider looking in; partly because he doesn't want to deal with the manifold meetings and logistics Opie has to; and partly because he just doesn't want to identify as a radio host

"I'm a comedian," he tells me later at the Olive Tree. "See, the problem with Opie and Anthony—where both of those guys struggled—is that they were married to each other. They were so used to bouncing off another person that when they split up, they're both standing there like satellites saying, 'Okay, now what?' But with me, I've always had standup.

"You know, it's weird," he continues. "Radio has made comedy a little tough. You get used to talking for hours, just conversationally, so when you have to structure it into material, it's harder. You can't just talk off-the-cuff onstage in front of a live audience. Sometimes a crowd is like, 'How come he's different onstage than when he's on the radio?' But that's just how it is. There's no way you can talk for that many hours a day and be that loose on stage. By the nature of doing structured material—every segue, every connection would seem out of place in real conversation. So I'm a comedian first."

Jim Norton

A COMEDIAN FIRST, SURE, but that's just one facet of a much larger and remarkably unique system. Most Jim Norton fans who know him through the thousands of hours he's logged on Opie & Anthony—and that is where most of his fans know him from—are familiar with his most personal quirks, whether that be his history with prostitutes or his weird obsession with taking pictures with celebrities. Everyone knows that Jim loves Black Sabbath; has idolized Ozzy Osbourne his whole life; and in recent years has struck a quasi-personal relationship with Ozzy, who appeared in one of Norton's specials.

Another recurring theme is Norton's sobriety. If you've listened to him talk enough on the radio, you've heard the account of how he dropped out of high school to go to rehab and never graduated. These raw bits of experience have been hammered down into repeatable stories with beats, even jokes. One detail that always comes up when he tells this story is that, by attempting suicide, he ruined his chances for being deemed "Class Clown"—but the picture would look weird anyways, with his bandaged wrists and all.

Norton's early stint in rehab was the turning point when he first got sober and learned the power of self-discipline. Which, frankly, sounds like the a boring Faustian bargain, but is one all the same: He will have a career pushing the envelope in standup and calling out society on every little hypocrisy he notices, and in exchange he will give up any possible fun. No boozing or drugs, of course. But also no cake or rich food, and yes to gallons of green juice. No to smoking, yes to seeing a personal trainer daily.

And he's constantly living on a razor's edge of self-doubt that prevents him from enjoying success. (This, despite all the success he's had, both inside the comedy world and out-. Most recently, he popped up in the acclaimed indie film From Nowhere, about three undocumented teens in the Bronx, which just won the Narrative Spotlight Audience Award at SXSW.) "I feel like my career is a stagnant pile of shit, and there's nothing happening," Norton says. "I really do. And that is not always rational. I know that the way I feel is not always the way things are, but I'm very paranoid about stagnating. I'm very paranoid about failing."

L: Amy Schumer, photographed by Chris Clinton; R: Norton recreates the iconic shot.

As successful as he's been, he's surrounded by friends who become much more successful: Louis CK, Kevin Hart, Bill Burr, Amy Schumer. When Schumer was hit with a flurry of dubious joke-theft charges in January, she chose to go on record on The Jim Norton Advice Show, a weekly program he hosts on SiriusXM. Why there and not The New York Times? To begin, Norton mentored her at the start of her career in the New York standup scene circa 2010. But her appearance was also a sign of Norton's credibility in the community. It proved that his fans and colleagues still want what Norton is selling, even if he doesn't exactly know what it is yet.

ON STAGE AT THE COMEDY CELLAR, Norton talks about political correctness. After a bit tearing into a fellow airline passenger for taking a dog onboard as a "comfort animal," he brings the focus back to himself. "But then I have to think, as much as I hate that knee-jerk reaction, I don't want to also be the knee-jerk asshole who denies everything just because it's PC! If something's PC and it makes sense, and it's actually the right thing, I don't want to be so ignorant that I'm like 'fuck that.' I'm the last angry asshole standing behind the red line."

This is 10 minutes into his standard 15-minute set and Norton has his second audience of the day rolling. He finishes with a joke about the hypocrisy of celebrities who nitpick over pronouns for members of the trans community, but blanch at the thought of giving them the real respect they deserve: blowjobs. Norton is not so shy.

Elizabeth Griffin Esquire

After his set, I stayed for one more comic and then stepped outside. On MacDougal Street, I was in between Café Wha?, where Woody Allen, Lenny Bruce, and Richard Pryor performed in the 1960s, on one corner and Ben's Pizza, the shop from the opening credits of Louie, on the other. A line had already formed around the block for the Cellar's late show.

I wondered if Norton would be doing a third set, but then I received a text. It was Norton: "Had to take off, but stay as long as you'd like." I could only imagine who he texted next.