By Jonathan Miles

“Want to see the grimmest apartment ever?”

This is Justin Theroux, failing miserably as a Realtor as he leads me southward on Lafayette Street into the slanted afternoon sunlight. But Theroux isn’t selling. He’s guiding, and this stop — a wide charmless slab of a building at the juncture of Bleecker and Mulberry streets is so gray and dispiriting it seems to cloud over the early-summer day — is the first on a loose and spontaneous tour of his downtown-Manhattan haunts, both past and present. This one falls squarely into the former category, dating back to the early 1990s, when Theroux was cobbling together a sort-of living by hauling Sheetrock, painting murals in dance clubs, bartending, and, whenever possible, acting. He crouches on the sidewalk and points to a narrow slot of glass at ground level. “That was my window,” he says, inflecting the last word to denote that, as windows go, this one really doesn’t qualify. “And by the way, what you’re seeing there, that’s also the top of the ceiling.” It was a cut-rate basement hovel of an apartment, he explains, wedged so close to the boilers that “the temperature went up to 105 at night, and in the dead of winter you’d have to run the air conditioner to keep cool.” Trains coursing in and out of the nearby subway station rattled the walls every few minutes. “It was fucking horrible,” he says. “I think I lasted there a year. It was a long time. Total dark night of the soul.”

New Yorkers love trading these early-apartment horror stories — the bathtub in the kitchen, the drug dealer down the hall, the rat leaping from a box of Lucky Charms — and Theroux, dark night of the soul notwithstanding, is no different. That’s because — despite his Washington, D.C., upbringing and the new nest he’s currently feathering out in Los Angeles with his fiancée, Jennifer Aniston — Theroux is a man who seems incapable, as several of his friends say, of existing anywhere else, his lungs unfit to breathe any other variety of smog. “New York is so embedded in him,” says his good friend John Krasinski. “It’s in the fabric of what makes him him. He’s the quintessential New Yorker. “And while he “never looks set-designed,” as Krasinski says of his friend’s style, Theroux’s clothing often announces his citizenship, as it does today: black leather boots, cuffed black jeans, a faded gray pocket T-shirt layered atop a white T-shirt, a black baseball cap dangling from a rear belt loop — the uniform of someone who might’ve lugged a beat-up guitar case into CBGB back in its heyday. At 42 (he turns 43 this month), even his physical attributes seem citified: the licorice-colored hair bequeathed to him by his Italian ancestors, the way his widow’s peak and arching eyebrow lend his expressions a noirish cast.

Almost within sight of the old CBGB space, now occupied by a John Varvatos store, is Von, the Bleecker Street bar that was Theroux’s final place of employment before his acting career took off. Besides tending bar, he contributed artwork, including the stenciled rendition of the bar’s name that remains on the window. “That was me,” he says, like a graffiti artist identifying his tag. Also in Theroux’s “that was me” category: the hipster cheap-beer renaissance. “Yeah, I still take credit for the idea of selling cheap beer for lots of money,” he says. “It was a whim. I was like, ‘Wouldn’t it be funny to sell Schlitz and Pabst Blue Ribbon up there with all the great wheat beers?’ We added every horrible beer we could think of and charged four bucks for them. Those beers ended up outselling Chimay, everything. So that might’ve been me that started that and gave everyone the squirts. You’re welcome, Pabst.” (“I’ll bet if we dug deep enough,” says Krasinski of this claim, “we’d find that he was somehow behind whatever we think is cool.”)

The bar isn’t open yet, so we hike past another of Theroux’s old apartments to where Bleecker smacks into Bowery. “This was kinda my corner for the longest time,” he reflects. “Ten years.  I never thought I’d see the day when this was a fucking…” But he stops himself here, wary of the wistful lament, the downtowner’s cliché. “I’ve never been particularly nostalgic,” he explains. “I’m not sure whether nostalgia is a weakness or a strength. I lean toward weakness, because it takes you out of experiencing what’s cool if you’re constantly the guy who’s like, ‘Oh, this place used to be amazing, and now it’s shit.’ Because that’s not true. It’s the same reason I don’t keep pictures of friends and family around. I don’t need to be reminded that I have friends and family.”

Yet nostalgia is wired into every New Yorker’s psyche. As the novelist Colson Whitehead once wrote: “You are a New Yorker when what was there before is more real and solid than what is here now.” It’s part of the way New Yorkers track their relationship with the city. And every transplant, like a religious convert, can recall that moment when the city’s neon spirit first moved him, Theroux included. “I sound like a kid saying this, but I think I saw a movie when I was young, maybe Flashdance or Rocky something, and I remember thinking, I gotta fucking get there,” he says. “It actually wasn’t even New York in those movies, but it ended up becoming New York.” His first visit alone came at the tender age of 14, and he developed an instant teenage crush on the city. “It wasn’t even the old thing about if you can make it there, you can make it anywhere. It had nothing to do with that. You just really felt free. It felt like no one was going to judge you. You could disappear here and be more yourself than you’d ever been.”

The young man who came to New York City to disappear, however, has, in recent times, done anything but. There is his rippled, tattooed back towering over Times Square on a three-story-tall poster advertising his leading role on the acclaimed new HBO series The Leftovers, the latest project from the Lost co-creator Damon Lindelof, which premiered in June. And thanks to his two-year engagement to Aniston, there is Theroux on the covers of half the tabloids greeting people in supermarket checkout lines, his every coffee break documented by paparazzi and then scrutinized for any repercussions that said coffee break might be having on his upcoming marriage to America’s Sweetheart.

If there’s dissonance here, so be it. Justin Theroux is comfortable with dissonance. The slash that divides his identities in the public imagination — the difficult-to-place, chameleonic character actor-slash-Kimye-level tabloid fixture — is just one more slash in a life that’s lacerated with them. He’s collected and curated slashes, in some sense, in much the same way he once collected Art Deco cabinet knobs and Black Label beer cans and wooden tongue depressors and human teeth. His job title, for starters, is rife with them: actor-slash-writer-slash-director. The Hollywood hyphenate is hardly unique, sure, but dig a little deeper into Theroux’s résumé and peculiar sub-slashes start turning up: He’s one of the director David Lynch’s favorite ensemble players, an actor capable of conveying intellectual grit and weirdo gravitas with a single raised eyebrow, and yet — slash — he’s often the joker lurking at the fringes of Paul Rudd rom-coms. He directed a quiet and cool art-house movie, Dedication, just a few years before writing the screenplay for Iron Man 2. He’s a downtown-Manhattan diehard, yeah, but he’s also “bicoastal,” as he defines himself now, with a massive home in Bel Air where he and Aniston tend to a flock of chickens and three dogs.

From the time he arrived in New York, after graduating from Bennington College in 1993, he has been cultivating these slashes. Most would-be artists arrive in the big city with a single dream. Slashes are usually what happens when reality contaminates the dream — the actor-slash-waiter, the model-slash-bartender, that sort of thing. But Theroux came to New York City pre-hyphenate, bearing dual degrees in visual arts and drama to back his ambition to become a painter-slash-actor. “I had these two terrible careers,” he says. “I figured I’d throw both of them at the wall, and maybe one of them would sloppily stick.” To varying degrees, both did: For a time, he was a sort of artist-in-residence at the Palladium, the iconic Steve Rubell-Ian Schrager club on 14th Street that was the locus of nineties nightlife. “They’d bring these huge pieces of paper that you tear down, and I’d draw and paint while the club was happening, surrounded by women dancing in cages,” he recalls. “It was like a stage, like an artist on display, and they’d give me these huge fat markers and I’d draw something big. It was just part of that club-life circus back then.” On the acting side, there was off-Broadway theater, followed by roles in the 1996 film I Shot Andy Warhol and a smattering of Sex and the City episodes and even an appearance on Ally McBeal. “The seesaw sort of tilted toward acting,” he says. “But I was happy to do either of them.”

The word versatile is often used to praise actors, but it’s typically applied to their performance abilities, not to their temperaments or biographies. “J.T. is a renaissance man in the truest way,” says Robert Downey Jr., who befriended Theroux when he was a writer on Tropic Thunder and later brought him on to write the Iron Man sequel. “He can act, he can draw, write, direct, curate oddball collections — the whole deal.” (Theroux’s longtime friend Amy Sedaris would add one more skill to Downey’s list: “He’s a very good crafter. He once made me a bottle-cap catcher out of a coconut,” which she says will impress anyone who’s ever tried crafting with coconuts.) Lynch, who turbocharged Theroux’s acting career in 2001 when he cast him in Mulholland Drive, says Theroux’s multifacetedness is part of what makes him such “a modern man.” “The boundaries are breaking down,” Lynch says, “and everyone is doing many more things.”

“It’s only one lifetime that you have,” is how Theroux explains it as we dip into an antiques store on 22nd Street. “So you have to, in a weird way, keep pivoting on whatever it is you’re doing. Follow whatever it is that’s keeping your interest.” Though painting has fallen by the wayside, “I’m sure if everything else went away and I picked up a sketchbook again, it’d rekindle something,” he says. “I think I’m a little bit — I don’t want to say A.D.D., I don’t think I’m that, but I can get bored with something quickly.”

He’s at the store, Mantiques Modern, to check on an item he’s been eyeing for years: a three-foot-wide wooden replica of the famed Lion of Lucerne rock sculpture in Switzerland. “It’s amazing, isn’t it?” he says, staring at the sculpture through its glass case. “There’s something really noble about it.” In leaner times, Theroux used to scavenge his antiques from Dumpsters. “I used to garbage-pick,” he says. “It sounds much more disgusting than it is. You learn a lot about society by seeing what’s thrown away. During the period I was doing that, a lot of great stuff was being tossed. What do they call that now, ‘Ironweed chic’? Edison bulbs and all that shit. This was the stuff I was finding for free 15, 20 years ago.” The shop’s owner tells Theroux the price of the lion: $9,500. “Oh, it’s down,” Theroux says. “When I came in a few years ago, I think it was 14.” The owner offers to remove it from the case for Theroux to examine, but he passes. “Oh, I’ve pulled it out before,” he says, and sighs. “It’s one of those things I’ll just keep thinking about until I regret when it’s gone.”

Of all Theroux’s pursuits, the writing — which came last and which includes, besides Iron Man 2 and Tropic Thunder, the screenplays for Rock of Ages and the forthcoming Zoolander 2 — would seem the most ordained. His mother, Phyllis Theroux, is an essayist and a memoirist. One of his uncles is Paul Theroux, widely considered one of the greatest travel writers of the 20th century; another uncle is the novelist Alexander Theroux; and yet another is the translator Peter Theroux. His cousins are the celebrated British journalist Louis Theroux and the novelist Marcel Theroux. Art Buchwald and Kurt Vonnegut were some of the frequent guests at the family dinner table. (Theroux’s father, a corporate lawyer, exited the household in a divorce when Justin was in grade school.) Yet Theroux credits that heady, salonlike atmosphere with generating his sense of humor rather than any literary inclinations. “I wasn’t good at those conversations,” he says, which may have been partly because of the dyslexia he struggled with as a child. “I mean, there were dinner-table conversations with my uncle Paul when we’d start arguing about where the Crusades began. And at a certain point, I had nothing to add to that. Actually, from the very beginning, I had nothing to add to that. So you put your hand under your armpit and make a fart joke and you’ve done just as well in a way.”

“He’s incredibly funny and silly,” says Sedaris, who recalls buzzing Theroux on a visit to his apartment and then hearing his voice thunder over the intercom, “Amy, I’m not in love with you anymore — stop bothering me,” Sedaris standing mortified on the sidewalk as passersby withered her with pitying glances. “But he’s not annoying about it, like some people can be. He’s not always on.” What friends and directors tend to circle around is Theroux’s intelligence — offscreen and on. “Justin always has that mind going,” Lynch says. “He shows thinking on the screen. You can see his mind working.” Lindelof, unprompted, echoes that sentiment almost identically: “There’s a fierce intelligence to his acting. You can always see him thinking.”

Yet Theroux wasn’t an obvious choice to lead a dark, theologically knotty cable series, in which he plays a small-town police chief grappling with the aftermath of a Rapture-like event in which 2 percent of the world’s population has disappeared into thin air, like popped soap bubbles. “He’s a little unknown — a bit of a cipher,” Lindelof says. “That’s exciting to me. There’s a where-did-this-guy-come-from aspect to Justin that’s really fascinating.” That cipher quality stems from the roles Theroux’s taken over the years, which, despite his dramatic turns with Lynch and others, have tended toward the comic end. That’s another enigma about Theroux that Lidelof savors: “Very few actors can move between a comedy and a drama space. It’s not always clear which is the true Justin. Is he the goofball with his shirt off playing guitar in Wanderlust, or is he the dramatic actor? Which suit goes on more comfortably?”

“There are certain actors who can grab a woman by the back of her hair and plant a deep one on her and say something like ‘We gotta save the world,” and that’s not me,” Theroux says, excluding at least one cinematic suit. “I can’t not be outside of my body, making jokes about that dialogue. Some people do it really well and effectively because they have the charisma to pull that off. I just know that I don’t.”

“I don’t know that that classic leading man exists anymore,” says Tom Perrotta, who write the 2011 novel The Leftovers and co-created the series with Lindelof. “Justin is certainly handsome enough, but there’s an emotional awkwardness that’s pretty fascinating about him. He has this combination of outward strength and inward bewilderment.” That sense of bewilderment was crucial for a series about, well, a bewildering catastrophe and all its debilitating strains, and Perrotta and Lindelof suspect, with obvious hopes attached, that the series could provide Theroux with the defining character that’s so far eluded him. “I think this role is going to cement him in the public imagination,” Perrotta says.

In the meantime, however, that public imagination seems likely to remain fixated on his relationship with Aniston, whom Theroux met via their mutual friend Downey on the Tropic Thunder set in 2007, reconnected with on the set of Wanderlust three years later, and finally began dating in 2011, just before the film was released. They initially bonded, he says, over shared memories of gnomes and beeswax sculptures and other accoutrements of the Waldorf grade-schooling they both received. “He and Jen fell in a real, legit fashion,” says Downey, “and he was willing from the jump to make sacrifices.” Those sacrifices are the battalions of paparazzi that hound him and Aniston, whose love life has been in the tabloid crosshairs for more than a decade. “It doesn’t feel like a hardship, it doesn’t feel difficult,” Theroux says, while allowing that he’s seen photographers topple children in their frenzy to get a shot of him and Aniston. “It can be an annoyance, but it’s not the end of the world. You have to center on what its core thing is, which is that you met someone you fell in love with. It’s hard to explain. I just find myself wondering, What’s the big fucking deal?”

“That could completely blow up someone’s life,” says Krasinski of the tabloid glare. “But if anyone is built for such a bizarre shift in life, it’s Justin.” Theroux isn’t entirely unfamiliar with press attention to his personal life. His mother documented so much of his childhood in newspaper columns that when she once asked him an innocuous question about their bedtime ritual when he was 5, he looked at her and said, “Are you doing this for the Post or the Times?” But embarrassing print revelations by your mother are light-years removed from the headlines he spots while walking past newsstands. “It’s always based in fiction,” he says, citing the awkwardness of being congratulated by a Leftovers crew member on the twins that one of the tabloids had announced Aniston was expecting. “You just kind of ignore it, but then you also become reluctant to say anything about the relationship. I could say everything’s good, and then it’s reflected back as JUSTIN THEROUX: EVERYTHING’S GOOD? That just creates this echo chamber, and as it ricochets around the internet, it just gets wacky.”

“I would hate that,” says Sedaris, who was one in a car with Theroux and Aniston as they tried to outmaneuver trailing photographers (“thrilling but disturbing”). “On the other hand,” she says, “he’s just glowing. We don’t even need to get together and talk for me to know how he’s doing — I can see it on his face.” “I think Justin’s dealt with it gracefully,” says Krasinski, noting that it can be painful “to see one of your friends go through that cyclone.” But, he ads, “he does get a great girl at the end.”

Theroux’s Manhattan tour winds down at Washington Square Park, a past and present “hangout point,” where he commandeers a bench by the fountain as a tall guy strolls by wearing a sandwich-board sign advertising himself as a six-foot-seven Jew who’ll rap for you. “I don’t know about that,” Theroux says about him. “Looking a little goy in the back.” He obliges a pair of middle-aged female tourists who request a photograph with him and then congratulate him on his upcoming wedding. Such exchanges are still jarring to him, but, he says, “there are worse things than people being kind.” He’s still pivoting, still adjusting to all these new slashes in his life. “There’s a huge distinction,” he notes, between wanting to act and wanting to be a famous actor. Or between wanting to be a famous actor and wanting to wear that even stranger suit: that of a celebrity, known more for existing than for a body of work. “Most of the people that jump off buses in Hollywood just want to fucking ‘make it,'” he says. “And I never had that drive. Honestly. I could never visualize myself in that way. To me it seemed so cart-before-the-horse-y.”

Sinking low, he settles onto the bench. “I still think a long, slow road is always the better road,” Theroux says as he surveys the park that’s been his refuge for more than 20 years. “Or at least for me it’s been the better road.”