Timothy Olyphant's Moment Is Now, Then, and Always

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."

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."

If acting was going to be the endgame of a comedy career, why not jump straight into acting? Having gone to college with the "really pretty, really rich" children of a slew of famous actors, he had internalized the idea that acting could actually turn out to be be a lucrative and fulfilling career. So he took his shot. "I met an agent, and they were like, 'Well, you should start in the commercial department. If you can chew gum and scratch your head at the same time, you can get a commercial.' And a commercial agent called me and said, "You know there's a thing today. A Coke commercial. Looking for a guy in his mid-twenties, good-looking, jeans, t-shirt.' And I remember hanging up the phone thinking, I got this! He just described me to a T. I'm in! This is fucking done!"

Olyphant rolls his eyes so hard it’s like he’s trying to send his younger self a message. "And I remember walking into that waiting room and seeing a dozen fucking guys in jeans and t-shirts, all way fucking better-looking. I was like, 'These guys are so handsome. Oh, my God. There's a dozen really good looking dudes, and they're all wearing jeans and t-shirts!' And if nothing else, I became aware that perhaps looks alone [are not going to get me a job]."

Even in the brief time I’ve known him, I’ve come to recognize this as a story that has all the characteristics of a classic Timothy Olyphant anecdote: ironic, deadpan, and reflexively self-deprecating. This is a habit that makes Olyphant an enormously appealing guy to have a drink with. But it also makes him an unusually elusive conversationalist—quick to spar, but slow to drop his armor. I’m having a blast shooting the shit with Olyphant. But getting him to open up isn’t quite so easy.

After his ill-fated-commercial audition, Olyphant decided to get serious. He took acting classes—first at U.C. Irvine, and later with the legendary acting teacher William Esper—and pored over books by legendary thespians like Konstantin Stanislavski. "I didn't understand what he was talking about half the time, but I knew he was taking it very seriously," says Olyphant. "And I felt, in some way, he was giving me permission to want to be an actor. It felt somewhat like a connection to the people I'd studied and admired and respected so much in the art world. I thought, 'This guy is taking acting as seriously as Richard Serra takes sculpture. This guy is taking acting as seriously as John Baldessari is taking his art. Maybe it's not such a crazy idea.'"

Fresh out of acting class, Olyphant was offered a role on a soap opera; despite his wife’s urging, he turned it down, gambling that something better would come along. He turned out to be right. In the early years of his acting career, he appeared in small roles in The First Wives Club, Sex and the City, and—22-year-old spoiler alert—played the villain in Scream 2. He eventually landed a role as a scuzzy, sexy drug dealer in the ‘90s cult classic Go by pretending he was reading the role for the first time. In reality, it was the part he’d wanted all along. "I had fully prepared for that, and pretended like I hadn’t," he says. "I hope young actors starting out are paying attention. It's all fair. Work really fucking hard, and then act like you didn’t."

That sounds like a lot of work for somebody who exudes such an easygoing aura. "This is all a performance, buddy," he says, laughing. "It’s all a performance. You’re part of it."

Olyphant’s buzzy performance in Go—in which, among other things, he delivers the most trenchant critique of The Family Circus ever committed to film—also caught the attention of Hollywood. Bigger movies quickly followed, including a supporting role as a cop in the Jerry Bruckheimer-produced thriller Gone in Sixty Seconds. The other role offered to Olyphant at the time was in Red Planet—one of two movies in a brief, weird era when Hollywood decided audiences might be super into Mars.

"This is about Mars, but they’re going to shoot it in Iceland," Olyphant recalls thinking. "Iceland for Mars. With Val Kilmer and Tom Sizemore. Thing One and Thing Two. Or: Stay here in L.A. [for Gone in Sixty Seconds], drive around with Delroy Lindo. I was like, 'Drive around with Delroy Lindo! He's in the Spike Lee movies, I love that fucker.' Oh my God, I needed the money, too. My wife was pregnant. And I'd still be able to go to the hospital when the child was ready to go."

Olyphant has several positive things to say about filming Gone in Sixty Seconds. He does not have anything positive to say about his own performance. And when I suggest that there’s only so much a 10th-billed actor could do, playing a generic-brand cop opposite actors Nicolas Cage and Angelina Jolie, he looks at me like I’ve sprouted a third eyeball. "That's not true at all! Oh, my God. Not true at all. I could have made more of an effort. I could go back through all those mediocre things and go, 'Dude, here's the answer. That's what you should've done. That's what you could've done. Would've made a huge difference.'"

There were a few more flirtations with big-screen stardom, in movies like the barely-disguised Risky Business ripoff The Girl Next Door and the truly bizarre Stephen King adaptation Dreamcatcher—but in the end, Olyphant found his first truly great role on television in 2004. Fascinated by the way in which human beings start with chaos and hammer out the terms of a civilization, David Milch—justly revered as one of the great minds in TV history—sold HBO on a based-on-a-true-story western called Deadwood. The series begins in a rough, lawless settlement in 1876, in the territory that would eventually become South Dakota, as a motley ensemble of fortune-seekers squabble and collaborate to define the terms on which American civilization will be built—and, of course, to carve out a chunk of prosperity for themselves.

Most of Deadwood’s characters are based on real-life figures. Milch cast Olyphant as the show’s protagonist, Sheriff Seth Bullock, depicted here a righteous lawman with a wild temper boiling just under his skin. And Olyphant was very, very nervous about it. "I remember feeling a ton of pressure," he says. "Lead role. Don't let them figure out that you are not this guy. I just remember feeling like I was trying to get it right."

Deadwood had a famously unconventional production. David Milch’s writing style relies heavily on flashes of inspiration; entire scenes were sometimes written on the fly and filmed as soon as the actors he needed could be hustled to the set. The result was a show where forward momentum was almost always secondary to the depth of the characters and the dazzling, ornate patter of the dialogue. "No one ever said to me the greatest thing about Deadwood was the plot," Olyphant says, grinning wryly.

For three seasons, Deadwood was adored by critics. It earned solid ratings. It racked up a slew of nominations at the Emmys every year. Even as Seth Bullock gradually receded further into the show’s background to make room for Ian McShane’s Al Swearengen—who had shifted from Deadwood’s big villain to a second protagonist—it seemed obvious that Deadwood had enough story left in the tank to keep Olyphant gainfully employed for years.

And then, with basically no warning, it was over.

Since the show’s 2006 cancellation, there have been many, many attempts to puzzle out exactly what happened when Deadwood—still widely regarded as a crown jewel in the midst of HBO’s first golden era—suddenly ended, with its story maddeningly unfinished. Here, for the record, is the most honest and complete version Timothy Olyphant can tell me:

"After season two, Ian [McShane] and I said we wanted to renegotiate. Common practice. And especially because, in the first two seasons, Ian blew up huge because of the show. My position was, 'He’s going to get a lot. I bet they're going to give him a lot. I'll just take whatever he's getting.'

"Ian and I, through our reps, agreed that the best thing would be to start [filming] season three knowing we were moving in the right direction. As I recall, we shot a bunch of episodes—maybe as many as eight—before I remember getting the call saying, 'We closed.' We got big raises, and we were going to get checks for all the episodes we had already shot. Point being, I told my wife, 'Hey! We can buy that house! And conservatively—to be smart—we should only count on one more season. Maybe two. But let’s only count on one more.'

"Long story short: I'm only in that house a few weeks, and David calls me in the morning. [My wife] tells me it's David, which is unusual. I'm in the backyard of my new home. He says, 'Bad news. Show’s over.'" David felt he was getting the nudge. He said, 'When someone's walking you to the door, it's best just to leave.' And I, at that time, was like, 'Great, fuck it, I'm with you.'

"But as I understand it now, what David told me wasn't set in stone. He called me first. I called my rep and said 'Look, I just got off the phone with David. The show is over.' And it set off a brushfire. By noon, that was out of control, and no one could walk it back."

Did the fate of Deadwood really come down to a game of chicken and a game of telephone?

"HBO would not have given us raises for a show they were going to cancel. Why renegotiate with us? They could have just said, 'Look guys, fuck off, we're canceling the show.' There's no reason to give someone a raise because the show is a success if their intention is to cancel it."

So if everyone involved actually wanted Deadwood to come back after season three, who deserves the blame for that not happening?

"Look: It takes more that one person to make an accident. And so they all stepped in. To some degree, I guess I played a part. I didn't talk them off a ledge. I didn't say, 'No, David. Stop. This show is the greatest thing.' I was like, 'Sure. Let’s call it.'"

And given how quickly and needlessly it all fell apart, why was Olyphant so willing to accept the cancellation of Deadwood at the time?

"To put it in perspective: I felt somewhat relieved."

Nearly 15 years after it went off the air, Deadwood remains some of the most acclaimed and beloved work of Timothy Olyphant’s career. But like most of his earlier roles, Olyphant himself has a dimmer appraisal of his own work. "I wouldn't want to disparage it, because I know people enjoy it, but I feel like I wasn't consistent," he says. "There are times where I feel like I failed."

In some fascinating alternate universe, Timothy Olyphant starred in The Fast and the Furious. In ours, he turned down the role that eventually went to Vin Diesel. In a different fascinating alternate universe, he starred in Iron Man. In ours, he merely screen-tested on the same day as Robert Downey Jr. Talking to Olyphant about those what-ifs, it’s clear there have been other big roles nobody knows about that—for one reason or another—never came to pass.

Does he have regrets about any of it? "I'm telling you, man, I wouldn't have survived it. I got lucky. I was dodging a bullet," he says. "Don’t get me wrong. Being Iron Man would have been…" he pauses, choosing his words carefully. "I would have had a good time. But Iron Man taking his kid to a swim meet? That poor bastard. Those poor kids. It just comes with a lot. It's a whole different deal. That's the catch with this job. Success comes with a lot of baggage."

And that’s only a part of why he was willing to let Deadwood go. "I love that show. But the truth of that job—and I don't know how many of the other people involved feel this way, and if they did, if they would admit it… it was exhausting. It was stressful. No one knew when they were working. No one knew what their week was like. People have lives. As much as all of us sit back and say it was one of the greatest jobs—if not the greatest job we ever had—I also remember a bunch of actors, bitching like actors do. 'I guess I'm not in the show, I'm only working Tuesday." And you're like, 'Shut the fuck up, you're in the greatest show you'll ever be in in your life.'"

Now, the show was suddenly over, and Olyphant still had bills to pay. "Financially, I told them, 'I’m cool! No problem! Just come see my house before I have to sell it. You're going to love it, and it's about to go right back on the market.'" He leans back in his chair, almost winded by the memory. "Financially, it was terrible."

So he quickly accepted an offer to play the villain in the fourth Die Hard movie, and signed on for the lead role in Hitman—a feature adaptation of a video-game franchise that required Olyphant to shave off all his hair, along with any shred of his natural personality or charisma. "I remember being on the set on the first day, trying to do what the powers-that-be wanted, and I thought, God, this should have been a Vin Diesel movie," he says. "It’s a funny experience. There's so much money on the line, and there's so much pressure, that you assume everyone knows what they're doing. Apparently, that's not the case. Looking back, you're like, 'Well, if you're going to make a big stupid piece of shit—not that I'm saying it was, but if it was—I should have just done my thing. I should have just said, 'Look: This is what I'm going to do, and if you don't like it, tell me your idea. And if it's not any better, get somebody else.'"

If Hitman was a disaster (and it was), it was also a wake-up call. "When you find yourself in Eastern Europe—with your head shaved, in a movie that really you have no business doing, but you need the money—you start thinking: 'What do you want? It's not enough to just say you just want to be a star of a big movie.'"

Revisiting this pivot point now—a time when his career, resting on a knife’s edge, could easily have gone another way—Olyphant gets reflective about what he’s learned along the way. "You have to learn the difference between being a difficult asshole and being someone who is fully committed, and invested, and is going to trust their instincts and stick to their guns," he says. "And you have to be comfortable with the fact that that may make other people uncomfortable. And you have to realize that does not make you an asshole."

In the years since Live Free or Die Hard and Hitman, Olyphant has appeared in movies, but he’s done his best work on TV, balancing out his lead roles on Justified and Santa Clarita Diet with quirky guest spots on sitcoms like The Office, The Mindy Project, and The Grinder, on which he played a funhouse mirror-version of "Timothy Olyphant" as a smarmy douchebag, and ended up walking away with a Critic’s Choice Award for it.

It’s a road that, against all odds, finally led him back to Deadwood for the long-discussed movie—set 10 years after the events of the original series—which arrives on HBO on Friday. Despite years and years of begging from Deadwood fans, Olyphant admits that he never thought the movie would happen. He had a good reason to be skeptical: "I thought I would never do it. I thought, ’It probably wouldn't happen, and I don't want to do it, so the chances are really slim.'" Even when the movie finally got a finally got a green-light from HBO, Olyphant says he didn’t sign on "until the very, very last minute." He reconsidered after reading the script and thinking about all his co-stars from the original series. "It was a rare occasion where I realized that me saying 'no' affected people I knew," he says.

But now that the movie is in the can, he’s feeling a lot warmer about it. "I loved doing the movie. I didn't think I would," he says. "I’ve joked that I'm a fan of high school reunions, but I'm not a fan of repeating my sophomore year. But the truth is: The idea of repeating my sophomore year has some appeal. I imagine, like most people feel, like I didn't take enough of an advantage of school. The Deadwood movie, in a way, was a brief opportunity to go back and experience it with the perspective of just how special it was."

Which raises a different question: Now that Deadwood is back, is this also the end all over again? For years, the story had been that David Milch intended to make two Deadwood movies. But in addition to the normal hurdles that greet any large-scale production that’s full of in-demand actors, the Deadwood movie arrives under unexpectedly tragic circumstances. Last month, Milch disclosed that he had been diagnosed with Alzheimer’s disease, which he described as both "progressive" and "discouraging."

When I ask Olyphant about the future of Deadwood, we’ve been talking for the better part of two hours, and this is the only time I’m seen him struggle for words. "Look, everyone knows that David has been... about David and his health," he says. "I can't imagine that world coming out of anyone else's brain. And his brain is... All of us eventually have to deal with it. Life has gotten in the way. So I cannot imagine. The show is David."

Olyphant pauses, takes a drink, and gathers his thoughts. "Would I like to? After doing the movie? Yeah. I'd love to do more. But David and the show... you know. If HBO shows me somebody that's got that kind of brain. But I don't think one's out there. I haven't met him or her. And I've been around."

For an actor who habitually underplays his own accomplishments, Olyphant is having quite a year—even if Santa Clarita Diet has been cancelled just a few days before we met ("The new motto is, 'Netflix: Don’t get attached,'" he deadpans, channeling Don Draper at a pitch meeting.)

Next up is a role in Once Upon a Time … in Hollywood, a dream collaboration with Quentin Tarantino, which recently premiered to strong reviews at Cannes. With an array of 2019 roles that seems engineered, at last, to show the full range of what Olyphant can do—drama, comedy, period pieces, family films—it feels like his career could rocket off in a lot of different directions right now. And for the first time, he’s up for it. "The last 15 years, I was very unwilling to leave L.A.," he says. "Now, my kids are older. If someone says, 'It shoots in Budapest,' I say to my wife, 'Honey, you want to go live in Budapest for a while?' And why not?"

And there’s no Deadwood-esque Justified revival on the immediate horizon, but Raylan Givens is a role Olyphant hopes to play for the rest of his career. "If [they] want to come back three years from now, or ten years from now, and do a Raylan story—I'll do them until they say, 'Tim, you're too old.' I'll do them in a heartbeat. I would love nothing more than for that to happen."

By now, the cocktails are arriving unbidden. Whatever Olyphant says about the "sweet spot" of his fame, he and his white hat have been recognized. What Los Angeles bartender doesn’t want to brag about the time they sent a free bourbon to Seth Bullock?

And I’d be more than happy to stay. We’ve been here for two full hours, and I still feel like I’ve hardly scratched the surface. But no matter how good the drinks and the conversation—I’ll vouch for both—this isn’t an episode of Deadwood. We’re never going to stick around long enough to see the bottom of that bottle. Olyphant has already stayed longer than he intended, which feels like a particularly thoughtful concession from a guy who is so deliberate about where and how he spends his energy and his time. Now, it’s time for us to drop our half-finished glasses, shake hands, and amble off in opposite directions like… well, like two cowboys in a show that’s not as good as Deadwood.

Styling by Jon Tietz. Grooming by Kumi Craig.

Originally Appeared on GQ