You are prepared for a few things when you arrive for dinner with Timothy Olyphant. You suspect he will be handsome. (He is.) You suspect he will carry his handsomeness with the casual, self-possessed indifference that has made him television’s go-to cowboy. (He does.) You suspect he will order a whiskey cocktail, and after that, another whiskey cocktail. (He will, and he does.)

What you are not prepared for is the moment when Timothy Olyphant walks in, like he just stepped out of the pages of a Zane Grey novel, wearing a white cowboy hat.

It’s not quite the white Stetson he wore for six seasons on FX’s Justified—there’s a cheerful orange band on this one, and its brim is shorter—but it’s close enough to break my brain a little bit. So after the getting-to-know-you pleasantries are out of the way and the drinks have been ordered, I have to ask: Isn’t it a little risky for modern television’s most famous white hat-wearer to walk around looking like he’s cosplaying as Raylan Givens?

"Dude, I've lived a blessed life," he says, grinning widely. "You don't understand. I found a sweet spot. Nobody bugs me. I have it as good as it gets."

This sweet spot, as far as I can tell, is a happy accident—a byproduct of Olyphant being very good in the best things that never quite explode into the mainstream. He starred in Deadwood, the most under-appreciated show of HBO’s Golden Era; Justified, the most under-appreciated show of FX’s Golden Era; and Santa Clarita Diet, a perennially under-appreciated zom-rom-com which started good and got better every season. Netflix, in the inscrutable algorithmic wisdom of this Peak TV Era, decided to cancel it anyway.

Which means, for this brief moment, that Timothy Olyphant is between jobs. "I haven't worked in months," he says. "And I refuse to get a haircut unless somebody pays me. And that"—he pauses for emphasis, smiling—"encourages the hat."

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Olyphant grew up in Modesto, California. In one of his frequent late-night appearances on Conan, Olyphant describes an aimless, pranksterish-bordering-on-criminal adolescence: spraying fire extinguishers at cars, gift-wrapping cinderblocks and leaving them on the street, riding big blocks of ice up and down the hills at the local golf course. He was recruited to join USC’s swim team, and when I bring up his impressive record as a student athlete for his alma mater, USC—which has, uh, been in the news lately—Olyphant launches into an extremely entertaining, totally fake story about how his parents bribed the swim coach to pretend he was on the team. ("Full ride scholarship. I couldn't get across the pool without drowning," he mock-confesses.)

Olyphant decided to major in Fine Arts—partially because it fit around his swimming schedule, and partially because studying art, which he already loved, felt like "getting away with murder." After he graduated—and was suddenly forced to find a good answer when people asked, "What are you going to do with a Fine Arts degree?"—it was television that provided what seemed like an answer. Inspired by ABC’s thirtysomething and the promise of an office with a basketball hoop, Olyphant looked at jobs in advertising. But something else nagged at him—a sense that pursuing some of his more outsized ambitions would help him stave off a midlife crisis later.

So he tried performing. First, there was a brief stint as a stand-up comedian. (Olyphant says he remembers his entire routine, but flatly refuses to tell even a single joke from it.) And despite some promising gigs, he was already starting to think about the long game. "At best, the stand-up thing feels like it's just leading toward an acting job," he remembers thinking. "And I could see the whole thing unraveling in a few short years. I wouldn't even be 30 yet, and I'd be done. Chewed up, spit out. Cast on some sitcom, and not even good at what I do."