At 51 years old, Timothy Olyphant is perhaps TV’s most underappreciated actor, who became a staple of prestige TV thanks to his starring roles on HBO’s Deadwood and FX’s Justified. While the latter earned him an Emmy nomination, it’s the former that’s developed something of a cult following ever since it was abruptly canceled after three seasons in 2006.
On David Milch’s beloved Western drama about the lawless South Dakota camp in the 1870s, Olyphant played the brooding Seth Bullock, who begrudgingly becomes sheriff after first moving into town to start a hardware store with his business partner, Sol Star (John Hawkes). Soon after his arrival, he squares off with Gem saloon owner Al Swearengen (Ian McShane) and develops mixed emotions for widow Alma Garret (Molly Parker).
Just over a decade later, the series finally picked back up with a new HBO film -- a fitting final chapter to close out the saga that so many fans clamored for year after year. For Bullock, now a U.S. Marshal, that meant seeing his marriage with his brother’s widow, Martha (Anna Gunn), thrive, with the addition of new kids after her first son died in a horse accident. But as happy and settled as he was, the arrival of Garret and former foe, George Hearst (Gerald McRaney), threw Bullock back into the thick of things as old rivalries quickly reignited.
While it had been 13 years since Olyphant last embodied Bullock, he says “it all felt vaguely familiar.” On his first day of shooting, he recalls, “someone called action and I had some dialogue, and I thought, 'Well, I think I know what to do here. We’ll kinda see what happens.'” Ultimately, it was like riding a bike for the actor, who hoped that he would remember the important things while shaking loose the things that didn’t work out as well the first time around.
The end result was another restrained performance from Olyphant that may finally earn him a long overdue Emmy nomination for the role. “I gave it the old college try and I really enjoyed the whole process,” Olyphant says, admitting there was pressure “to honor the thing that it once was but not get too trapped in trying to do a greatest hits album. It was a f**king bear, but I’m very proud of it.”
While the film paid plenty of service to the dedicated fans who openly mourned the short-lived series, it was also a selfish act by the ensemble cast who are fiercely devoted to Milch, a prolific TV writer and producer who was diagnosed with Alzheimer’s ahead of making the film. “It’s all about David. With all due respect to the show and the story, that’s a really distant second,” Olyphant says. “It’s all about getting the opportunity to work with David again. That was the thing that had the greatest appeal to me.”
Working with Milch is what sets Deadwood apart from Olyphant’s experiences on any other project. “Acting is like sex and pizza. When it’s good, it’s good. And when it’s bad, it’s still pretty good,” he says. “But the ones that really, in my experience, have a real impact and lasting memory are the ones where the dialogue that was handed to you was truly something special. Like any great story, it makes you feel like you have a greater understanding of humanity.” The character Bullock, he adds, “is one of the good ones.”
While it might be easy to think an experience like that might spoil an actor for anything else, Olyphant says that “Deadwood sort of informed how I went to work on” Justified, on which he played U.S. Marshal Raylan Givens for six seasons. “I think I was maybe a little wiser at that point,” he says, adding that his experience on the FX series was more of a “team effort.”
In the years that followed, he’s played on his All-American looks and brooding stare, with guest roles on Archer, The Grinder and The Office. Most recently, he let loose opposite Drew Barrymore on the lowkey Netflix zombie comedy, Santa Clarita Diet, which was recently canceled after three seasons.
Despite what was another abrupt cancellation -- the news came a month after season three debuted in March -- Olyphant’s handling the news better this time around. “The fact is, it’s what everyone signed up for -- the unknowing,” he says, adding: “As long as I’m not broke, I’m OK with it.”
In the meantime, Olyphant will next be seen in Quentin Tarantino’s star-studded Once Upon a Time in Hollywood. While Leonardo DiCaprio and Brad Pitt play fictional characters, Olyphant is bringing one of the ‘60s biggest stars back to life, portraying Western TV actor James Stacy. Despite being in another cowboy hat, there was no hesitation at all about joining the film. “Who gives a sh*t? I don’t care if you were telling me I was wearing a chef’s hat, I’m going to be there,” he says.
As for Deadwood: The Movie, the actor says he doesn’t take any of his time on it lightly, especially now that this long journey is now complete. “It was a joy to work on and the fact that it’s being so well-received is no small thing,” Olyphant says.