Justin Theroux was crouched in the passenger seat of a black Chevrolet Suburban creeping through the Lower East Side of Manhattan, looking exactly like you would expect Justin Theroux to look, wearing a black T-shirt, gold aviators and a black Wu-Tang cap pulled low.
It was around 11:30 p.m. on a sweltering Wednesday in August, and he was out on the town with his boys, in this case, the director Cary Joji Fukunaga and the night life impresario Carlos Quirarte. Nights like this happen a lot these days. Mr. Theroux, as you may have heard, is single again.
The evening began with a spirited dinner at Lilia, the impossible-to-get-into pasta temple in the Williamsburg neighborhood of Brooklyn. Conversations touched on fake news (“There are now actually people who believe the world is flat,” Mr. Theroux said) and D.N.A. ancestry kits (“Part Italian, part French,” he said, to which Mr. Quirarte added, “and 100 percent hot,” without missing a beat).
Sipping a double Tito’s with soda and three limes (never two, never four), Mr. Theroux joked that he wanted to keep the giant robotic sex toy that his character wears in “Maniac,” Mr. Fukunaga’s mind-melding new Netflix psychological thriller, as a souvenir.
“Certain props you always want to bring home,” Mr. Theroux said. “I’m sure Charlie Chaplin has his cane. I’ll have my self-masturbating virtual reality suck tube.”
After dinner, the crew took an Uber S.U.V. back to Manhattan. In the front seat, Mr. Theroux got a text from Alexander Skarsgard, who was at the Flower Shop, a faux-dive bar on Orchard Street that draws slumming actors and models.
A little past midnight, Mr. Theroux and friends were whisked past the velvet rope and headed downstairs to the mock hunting lodge, where he joked with a model in denim micro-shorts and bro-hugged Mr. Skarsgard by the pool table, before grabbing a cue and challenging a young couple to a game.
Crouching to break, he connected with authority, scattering the balls violently around the felt. With the barest hint of a smile, Mr. Theroux coolly rose to chalk his cue.
A ‘Meta’ Profile
“Man, you left too early,” Mr. Theroux said when I met him outside his Greenwich Village duplex around 1 p.m. the next day. “I played the best game of my life. Ran the table. The other guys didn’t even get off a shot.”
Despite the 90 degree weather, he wore a biker-chic ensemble familiar from countless Justin Theroux paparazzi fashion spreads: ripped black jeans, suede Common Projects boots, Vuitton belt and a sleeveless gray T-shirt that showed off his howitzer-scale guns.
Mr. Theroux does not wear shorts, even on days when the denim clings to your thighs like paint. “We all have a uniform,” he said.
Our plans were still fuzzy. For the last couple of days we had been discussing how to approach this article, his first in-depth interview since his tabloid-quaking split with Jennifer Aniston in February.
Mr. Theroux is an ironist by nature, and his instincts tilt toward the meta. In his role as style influencer, for instance, he helped turn cheap, counterfeit Gucci T-shirts into a fashion micro-craze. When I first profiled him in 2007, he framed our night out as a mock-“Wild One” ride from hell, complete with hypothetical biker gang, which he bestowed with a self-consciously moronic name, Die Fast.
Attempting to fit him into a standard celebrity profile seemed like a foolish venture, as if commissioning Jeff Koons for a family portrait. And as Mr. Theroux would point out, he has spent the last three years dodging the kind of tabloid glare he never asked for.
Once a matinee idol for the art house set, thanks to the cerebral, aloof demeanor and subtly anarchic wit he displayed in cult favorites like “American Psycho” and “Mulholland Drive,” the celebrity-industrial complex transformed him from an actor that cool people knew into an actor everyone knew.
The tabloids cast him as the motorcycle-riding bad boy who rode off with “America’s sweetheart” and saddled him with the no-win nickname “Mr. Jennifer Aniston.”
Since the split, the glare has scarcely dimmed, as paparazzi stake out his black Ducati, leaving his shiny gold bicycle (with a red Supreme sticker) as his primary two-wheeled transportation. New York tabloids have had a field day inventing narratives for him. Justin Theroux spotted with mystery woman! Justin Theroux parties with so-and-so!
So excuse him if he wants to have a little fun with the news media when the news media comes buzzing at his door on a late-summer afternoon. He joked about making the article a parody of the fish-out-out-of-water celebrity profiles of the 1990s, in which a journalist and a movie star would play, say, laser tag in Times Square.
“Let’s do something really touristy,” Mr. Theroux said, whipping out his iPhone and Googling “tourist activities NYC.” Before long, we struck on a plan: to wander through his old haunts on the Lower East Side, then hit the Statue of Liberty.
“It will be ‘fish out of water,’” he said, “in my own fishbowl.’”
No Longer a ‘House Cat’
From his apartment, we headed to Washington Square Park with Kuma, his gray rescue pit bull, leading the way.
Despite his star-worthy shades, glimmering gold Rolex and loping gunfighter gait, Mr. Theroux moved freely among the half-clothed 20-somethings lounging in the grass. No one asked for selfies, no long lenses peered at him from the bushes. “It’s like weather,” he said of the paparazzi. “Sometimes it blows in hard and wet, sometimes it’s just gray.”
Heading east on West Fourth Street, we wandered to the Hole, a gallery on the Bowery that featured a show by Alleged Gallery, an incubator for artists including Shepard Fairey and Cheryl Dunn, where Mr. Theroux used to hang out when he was in his 20s.
He arrived in New York in the early 1990s with a creative pedigree. His mother, Phyllis Theroux, was a style reporter for The Washington Post; his uncle is the writer Paul Theroux. Justin had studied drama and visual art at Bennington College and moved to New York with a vague plan to pursue both.
Perusing works by Rita Ackermann and Tom Sachs in the pink-floored gallery, he recalled his days as a struggling postgraduate. “When all this stuff was affordable, I couldn’t afford it,” he said. “That’s the curse of being in the scene and not of it.”
After the gallery, we wandered south, toward Chinatown. On the corner of Bowery and Canal, a tattooed woman in a checkered mini-dress and a young boy stooped to pet Kuma, seemingly oblivious to her tabloid-famous master.
Mr. Theroux seemed to relish the anonymity. Although he has divided his time between New York and Los Angeles for decades, New York, he said, is home. “Life there is a very gate-to-gate, garage-to-garage, car-to-car, and that’s just for anybody,” he said of Los Angeles. “There is this kind of hermetic seal that’s placed around you.”
“For me, at least, it can very quickly turn you into a house cat,” he added, “in that you’re perceiving what’s going on around you through panes of glass: your windshield, your driver’s side door, your rearview mirror.”
“In New York,” he said, “the minute you shut your door behind you, you’re out in it.”
Passing souvenir stalls and dumpling shops, Mr. Theroux spoke of his affection for Chinatown, which he often wanders alone. He lived in China during college and speaks better-than-passable Mandarin.
“It is kind of like a great Britney Spears song, where you put on your headphones, and there’s so much overproduced, bubble-gum, sweet poppy goo, but in a good way,” he said. “There are these little robotic things clanking, and then there’s a big tub of turtles, the weird little lucky cats with their paws moving back and forth. It’s like a dream sequence from that Japanese anime movie ‘Paprika.’”
‘It Was Heartbreaking’
With our clothes damp with sweat, we decided to cool off at Von, a bar on Bleecker Street where he was once a bartender.
At midday, the lights were low and the bar was empty, so we settled into a corner table that felt as private as a confession booth. It seemed like a safe place to broach the subject of his marriage, about which he has said nothing publicly since he and Ms. Aniston issued a brief joint statement in February, describing themselves as “two best friends who have decided to part ways as a couple.”
Mr. Theroux let out a long exhale, aware that anything he says on the topic will get sliced and diced into nonsense on social media. “That’s why I don’t go on Twitter,” he said. “With the internet, it’s too inelegant a machine to accurately carve truth.”
With seemingly nothing to go on, the tabloids have speculated endlessly on the reasons for the split, which usually boil down to him being too edgy and New York for the sunny Los Angeles rom-com star.
“How do you combat gossip and rumor?” he said. “And it’s just on crack and steroids now.”
He was under no illusions about the scrutiny the couple would face. Early on, his friend Jason Bateman told him: “‘There will be this other “you” born, this other character. And this person is insane. If you follow this person, or you pay attention to this person, it will make you insane too,’” he said. “So I learned early on, obviously, not to participate, not to spend time dwelling on it.”
Now that the relationship is over, Mr. Theroux does not feel like he owes the public an explanation.
“The good news is that was probably the most — I’m choosing my words really carefully — it was kind of the most gentle separation, in that there was no animosity,” he said, neither defensive nor bitter. “In a weird way, just sort of navigating the inevitable perception of it is the exhausting part.”
“These are actually in reality small events that take place,” he continued. “But everything can feel like 10 on the Richter scale if you make the headline big enough and salacious enough.”
He took a breath and tried to elucidate the curious nature of a Hollywood marriage. Because acting is “kind of a carny lifestyle,” he said, with frequent separations a part of the job description, the split “doesn’t have that seismic shift of an ordinary couple, where everything is, like, you have to tear a baby in half.”
Far from meta, he sounded earnest. “Again, neither one of us is dead, neither one of us is looking to throw hatchets at each other,” he said. “It’s more like, it’s amicable. It’s boring, but, you know, we respected each other enough that it was as painless as it could be.”
“It was heartbreaking,” he added, “only in the sense that the friendship would not be the same, as far as just the day to day. But the friendship is shifting and changing, you know, so that part is something that we’re both very proud of.”
A few days later, when I asked if he was currently seeing anyone, he laughed. “Is this the part where I coyly raise an eyebrow and not answer the question?” he said.
From the outside, at least, his marriage to Ms. Aniston seemed to vault Mr. Theroux into a new level of fame. Suddenly, he was on the cover of magazines, marching down the red carpet with his megastar wife, sharing his manscaping habits with Ellen DeGeneres.
Mr. Theroux disagrees. “I still don’t know creatively if it’s had an impact,” he said. “I don’t feel like it has.”
Either way, his Hollywood career is as busy as it has ever been. This year, he appeared with Mila Kunis in “The Spy Who Dumped Me” and with Felicity Jones in “On the Basis of Sex,” the forthcoming biopic on Ruth Bader Ginsburg.
He recently flew to London to record the voice for the Tramp for the live-animated reboot of the “Lady and the Tramp,” opposite Tessa Thompson, for Disney’s new streaming channel (set to debut in 2019).
In “Maniac,” a futuristic, Kubrick-inflected black comic thriller about a pharmaceutical experiment gone wrong, Mr. Theroux is a guest star to Emma Stone and Jonah Hill. His indelibly odd performance as a mercurial medical genius “injects the show with this syringe full of wackadoodle energy, leaving the viewers wondering what in God’s name this show is about,” said Mr. Fukunaga, who was just named as director for the next James Bond film.
Mr. Theroux did not mind ceding top billing for a passion project at this stage in his career arc. “I wouldn’t even call it an arc,” he said, sipping his green juice at Von. “It’s more like some sort of cardiogram graph.”
His career has been marked not by a single breakthrough, but by a series of small ones. He enjoyed a mainstream breakout of sorts as a vindictive Irish mob leader in “Charlie’s Angels: Full Throttle,” from 2003. His screenplay (yes, he is a screenwriter, too) for “Tropic Thunder,” the boundary-pushing 2008 satire of Vietnam films, or really, Hollywood, which he wrote with Ben Stiller and Etan Cohen, was as subtle as a napalm strike, but resulted in an “Animal House” for the “Jackass” generation.
Mr. Theroux appeared to graduate to leading-man status with his starring role in “The Leftovers,” the critically acclaimed HBO series about a mysterious mass disappearance of 2 percent of the world population, which concluded last year after three seasons.
But conventional stardom has never been Mr. Theroux’s goal, said Damon Lindelof, a creator of “The Leftovers.” “I’ve always believed that Justin is a character actor that was cursed with being born into the body of a matinee idol,” Mr. Lindelof said.
A career without a single dominant moment so far is O.K. with Mr. Theroux. “Some people’s cardiogram just starts scribbling wildly at the age of 18, and it feels terrible for those people,” he said.
Too big a role too early, and you can be typecast forever. On the other hand, he said, “I’ve been either cursed or blessed with having a nice slow road. I’m like, ‘Good God, if I ever had a defining role, that’s a real yoke to have to wear.’”
Tourist for a Day
With the afternoon temperatures still hovering around brick pizza oven levels, Mr. Theroux and I decided to skip the long boat ride to Lady Liberty and headed to the Empire State Building instead.
Arriving in the soaring Art Deco lobby, Mr. Theroux was in a puckish mood. He mugged in front of a photo of Tony Danza in the celebrity gallery, cooed at the souvenirs in the gift shop (“Now this is the jam,” he said, holding up a tacky T-shirt of the Empire State Building), and feigned horror at the $65 express ticket to the top. (“How much for the elevator down?” he said.)
As he moved through a throng of tourists from Europe and Asia, few seemed to recognize him. He smiled politely when a skinny guard said, “You look just like Justin Theroux.”
When we arrived on the 86th floor observation deck, Mr. Theroux made halfhearted attempts to play tourist in his own city. “I’m sure no one has ever said this,” he said, peering over the railing, “but the people look like ants from up here!”
Looking at Lady Liberty in the distance, he added, “I feel kind of creepy, looking at a woman through binoculars.”
All jokes aside, I pointed out that there was an inescapable symbolism to the moment: He had started out on those streets below so many years before, broke and anonymous. Now he was a big Hollywood star, staring down at the city from the pinnacle of fame.
Mr. Theroux raised an eyebrow at the thought of himself at any pinnacle.
“If you want symbolism,” he said with a hearty chuckle, “we should go to, like, the 23rd floor.”