Welcome to Always Great, a new Awards Insider column in which we speak with Hollywood’s greatest undersung actors in career-spanning conversations. In this entry, Stephen Root reflects on his journey from Broadway to Hollywood—and from silly sitcoms to gritty HBO hits, including Barry and the final season of Succession. 

HBO has plenty of star power, but on one particular Sunday night this April, the network was ruled by a single character actor. We all expected to see Stephen Root as part of the final-season debut of Barry, in which he stars as the titular antihero’s mentor turned antagonist, Fuches. But an hour before that dark comedy’s season premiere got going, Root reprised another role in another beloved series on its way out, Succession. As political donor Ron Petkus, he returned to eulogize Logan Roy (Brian Cox) in exceedingly flattering terms at the late patriarch’s wake, to the great horror of his children. They’re wildly different roles, and Root, as ever, shines in both. “To be able to do all that in one night was pretty great,” he says with a smile over Zoom. “I think that’s the best it’ll ever get—don’t you?”

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From our vantage point, it’s been pretty great for a while. This may not even be the first time Root has taken over a night of TV in such a manner. (One will have to check the TV Guide archives.) On HBO alone, of late he’s appeared in True Blood, Boardwalk Empire, The Newsroom, All the Way, Veep, and Perry Mason; within that 15-year timespan, he’s also done Fargo, Brooklyn Nine-Nine, The Big Bang Theory, The Good Wife, Raising Hope, Fringe, Justified, Californication, and many, many more. That’s to say nothing of the independent movie credits he’s racked up, or his beloved voice work on King of the Hill and other animated series. Root has acquired the reputation of a guy who can get just about any kind of job done; he’s proven equally adept and comfortable in the silliest of sitcoms and the gravest of dramas.

Still, with small roles come specific types on either end of those spectrums. In Barry, for the first time, Root has gotten a chance to use everything he’s got in one package—a layered, funny-scary performance that’s netted him his first (very overdue) Emmy nomination and the sort of character arc too rarely afforded to actors of his profile. “I feel like the luckiest guy ever, at this late in my career, to be able to have something that special,” Root says. Call it the happy result of 35 years of hustle.

After attending college in Florida, Root came to New York in the mid-’80s with stage training, specifically Shakespeare, and an offer to do a whole bunch of plays on the road. He was known for playing the Bard’s clowns and jesters, and wound up touring for nine months with the National Shakespeare Company. After returning to New York, he nabbed back-to-back starring roles on Broadway, in So Long on Lonely Street and All My Sons; he later joined the national tour of Driving Miss Daisy opposite Julie Harris. 

He moved to LA at the beginning of the ’90s; his mentality had shifted to the screen, to booking as many jobs as possible, given that he had a new child to take care of. In 1991 alone, he amassed eight screen credits, establishing a particular sitcom niche in series like Home Improvement and Davis Rules. “The mash-up of a sitcom, which is audience and camera—I felt comfortable in front of an audience, having done theater forever,” Root says. “I was doing so many auditions for sitcoms that I think all the casting directors around town saw me as a quirky guy. It’s a strength of mine to do quirky guys, but when you get put into that little slot for a year or two, then it becomes sedentary.”

That familiar, complex industry bargain was highlighted most by Root’s breakout turn in NewsRadio, the critical darling that ran from 1995–1999. Root’s chummy, conspiratorial, micromanaging billionaire boss Jimmy James dominates just about every scene he’s in—despite the killer ensemble, including Phil Hartman and Maura Tierney—and cemented him as a comedy pro and a brilliant blowhard. He now cites his favorite episode as “Super Karate Monkey Death Car,” in which James boldly reads from the very poorly translated Japanese rerelease of his memoir at an author event; Root sells every note of the book’s ingenious stupidity, and many critics now regard it as one of one of the great sitcom episodes ever. But the show never had much of a chance to break out. “The NBC programmer hated us for reasons we don’t know,” Root says. “We had seven [schedule] moves in all, so it really didn’t have a chance to become a staple like a regular Thursday night NBC show would’ve been able to do.” Keep in mind, the show aired on the same network as Friends and Seinfeld, in the same years both were on the air.

If NewsRadio had been properly promoted and rose to those series’s level of hit status, Root’s career may have gone a different way. During its run, he also guest-starred on Larry David’s last pre-finale Seinfeld episode—he says he’s still recognized for that guest role more than almost anything else in public—and starred in Mike Judge’s cult hit Office Space, which, like NewsRadio, wouldn’t go on to be more widely seen until years later. Despite that résumé of excellent, now classic work, he saw himself stuck headed into the 2000s. He did another sitcom, Ladies Man, with writing “not nearly as good as what I’d been on.” After that show’s cancellation, he felt like he needed a change. So he walked away from comedy auditions. “I just stopped taking them,” he says. “I made a conscious choice. The risk that I took was good, because then you just don't get seen as one thing…. You have to educate [casting directors] as well.”

Root had what he calls a “balloon” in King of the Hill, Fox’s animated hit which ran for over a decade, and in which he was a regular cast member, voicing the dopey neighbor Bill Dauterive. “It’s a luxury that certainly most of the character actors that I knew at that time did not have,” he says. He earned a steady paycheck as he struggled to build a dramatic résumé—but with persistence, he pulled it off, eventually landing a key recurring arc on The West Wing as the piggish speechwriter for Republican Arnold Vinick (Alan Alda). “My first day on West Wing was a big deal for me,” Root says. “I was a huge fan of that show, and it was an enormous thrill to walk on and walk by all these people that you really looked up to.” 

All the while, in film, he’d established himself with some major filmmakers, most notably the Coen brothers. He first auditioned for them in O Brother, Where Art Thou?, in which he played the blind radio-station manager Mr. Lund. He remembers his audition vividly, making a big physical choice that stopped the room in its tracks. He took off his glasses, adopted the very broad expression that’d go on to define the character, and took both directors aback. “I had a strong choice in mind,” he says with a laugh. The Coens brought him back for a smaller role in No Country for Old Men, maybe their darkest movie. In that, he found a mini kind of back-and-forth between comedy and tragedy—the veering that he came of age doing in Shakespeare, and had been trying to pull off in his career onscreen ever since.

You can trace Root’s current, robust relationship with HBO back to True Blood, in which he was cast especially against type in the megahit’s first season as a lonely gay vampire forever stuck in middle age. Oddly enough given his résumé, Root was actually offered the part—and gives a creepy, sweet, sad performance, suffused with longing. “Amazingly, wonderfully different—I’d never had an opportunity to play a gay character, and especially one that has a romantic scene,” he says. “It was a nice, long arc where I could show pretty much his deepest feelings, and I hadn’t been able to do that before.” 

Root would go on to have meaty arcs in other HBO dramas like Boardwalk Empire and Perry Mason, similarly relishing the chance to showcase his dramatic bona fides. He tells me that even as he’d all but shed his initial, more limiting Hollywood reputation, most every time he’d arrive on a new set, he’d be greeted with a particular gift. “There are very, very few sets that I haven’t arrived at where in each trailer is a box of staplers,” he says—referencing the famous red prop on his character’s desk in Office Space. “Every generation, every six or seven years, a new group of people explore and find Office Space. The fact that they’re still discovering that kind of film is amazing to me.”

On Barry, Root has taken Fuches from the archetype of troubled, loving uncle to something much more sinister—if still with some vulnerability lurking underneath. The character is now sharing prison time with his old mentee, undergoing a major transformation as he adjusts to life on the inside. “It walks the line between brilliantly subtle character comedy and really violent drama,” Root says. “It’s a show that feels like family.”

I sense Root getting a little nostalgic as we build toward the present in our interview. After all, a lot of things are coming full circle. For his latest Coen collaboration, for instance, he played The Porter in Joel Coen’s The Tragedy of Macbeth—the first time he’d ever gotten to do Shakespeare onscreen. “I remember very distinctly talking to Joel at the premiere of Buster Scruggs [in 2018] and having a drink with him, and he said, ‘You’ve done some Shakespeare, right?’” Root recalls. Years later, Root made good on his training with the hilariously pitched mid-film interruption that the part has promised for centuries. “It was astonishing to be able to do that,” he says.

Then Root’s got King of the Hill coming back, marking another Mike Judge reunion. The actor reveals they did their first table read for the Hulu reboot just the day before our interview, and everyone got right back into the groove like nothing had changed. “Like riding a bike,” he says. “It didn’t take four seconds into the first read of the first page.”

So what’s next—what can be next with, as IMDb reveals, a neat 279 credits to his name? I ask about Root taking on a lead role one day. “Just to be a working character actor was my goal, and I feel like I’ve done that, and that’s okay,” he says. “Would it be nice to have a lead in a film? Sure, and maybe that will come. He adds, “But I can’t complain.”