Justin Theroux on the Biggest Challenge with Marrying Jennifer Aniston

It was never about just being an actor for Theroux-there was always writing and painting and myriad other bohemian pursuits. We know him as a character actor-slash-screenwriter-slash-tabloid staple (Don't pretend you aren't aware he's engaged to Jennifer Aniston). And thanks to HBO's Hot new series The Leftovers, he's about to be something more: a married man-slash-star in his own right.


By: Jonathan Miles

What's it like being engaged to Jennifer Aniston?
What's it like being engaged to Jennifer Aniston?

"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 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."

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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.

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