About 20 years ago, Jeff Hiller auditioned to play Kenneth Parcell, the demonically sunny NBC page ultimately portrayed by Jack McBrayer, in the pilot of 30 Rock. As things tended to go for Hiller back then, he did not get the job. 

“We all knew it was written for Jack, so I never even pretended that I was going to get it,” Hiller says now. But then, a surprise silver lining: “Tina Fey called me back and was like, ‘You’ve got really good timing’ — which kept me going for several years.” 

Fey went on to cast Hiller as a hotel clerk in 30 Rock’s third season — and, in a true rarity for any actor not named Rachel Dratch, brought him back years later to play a completely different character. 

That second role, as a flight attendant, came as an offer — no audition needed. “That had never happened in my entire career and has only happened two or three times since,” Hiller says. “It was a huge surprise, and it made me feel so proud.”

The Upright Citizens Brigade alum credits that experience with sustaining him and keeping him motivated amid several slow periods before, during and after. Indeed, it would be another decade before Hiller secured his first regular role on a TV series, HBO’s indie comedy Somebody Somewhere — a naturalistic, moving three-season performance that culminated in a shocking Emmy win for best supporting actor last year. 

“It was the dream all along,” he says. “After our first season, when no one really had heard of the show or paid attention, I still was like, ‘I don’t care — I get to be on that set.’ ” Now he’s back on the guest-star circuit with a slew of standout performances in acclaimed shows this past season, including Pluribus, Elsbeth, Stumble, Ghosts and Widow’s Bay. “I feel like I get more respect,” says Hiller of what’s changed since that Emmy triumph. Case in point: “I had been offered a role of the Not Murderer on Elsbeth, and then when I won an Emmy, I got the Murderer role,” he says — putting him in iconic company among Elsbeth’s season three killers: Dianne Wiest, Patti LuPone, J. Smith-Cameron, Julia Fox, Steve Buscemi and more.

“I murdered someone with a curling iron,” Hiller cheers.

No recent performance of Hiller’s looms as large, though, as his warmly cryptic episodic turn on Pluribus as Larry the friendly biker (complete with fabulous bike shorts). As she realizes the scope of what she’s up against with the smiley Hive Mind surrounding her, Carol (Rhea Seehorn) summons one such member, Larry, to ask for his opinion — and then, for her deceased wife’s opinions, since he can access them — about the books she wrote before an alien virus upended the planet. His answers are bizarrely indirect, which leads Carol to the crucial discovery that the Hive cannot lie to her. But Larry also shares a story about how her work touched people, resonating in large part due to Hiller’s sensitive touch. 

Hiller believes he got the part because one of creator Vince Gilligan’s employees was a Somebody Somewhere fan: “He saw my audition and was like, ‘Oh, I like this guy!’ ” He had little information when he first put himself up for the gig and knew nothing of Pluribus’ mythology, only given the direction that “you are her father and you’re talking to her about her dead mother” (yeah, not exactly). Once he got the job, he still had to fill in plenty of blanks. Seehorn proved a key resource to lean on: “She does not get many days off. She’s in every scene, so her time off is precious. But she generously invited me over and we rehearsed the scene.

“The big thing that they kept telling me was, ‘You love her so much, her work means so much to you,’ so I tried to hit that,” he continues. “But I also didn’t know that they eat bones!” 

When the show finally started airing, Hiller found himself in a strange spot. “I kept forgetting that I was in it,” he says. “Then I was like, ‘Wait, I’m in episode four! I can’t believe I’m a part of a zeitgeist moment.’”

Of course, it’s not the first time Hiller has appeared on a hit show. Beyond 30 Rock, he’s made the most of small appearances on Broad City, Ugly Betty, Crazy Ex-Girlfriend and American Horror Story. He’s currently recurring on Widow’s Bay — Apple TV’s horror comedy gaining steam with critics and audiences — as one of the aloof employees in the office of the mayor (Matthew Rhys). “That came through my friend [creator] Katie Dippold,” he says. “I don’t know what I would’ve done if I didn’t start at the UCB. I guess I’d just be unemployed.” 

Yet while Hiller has been seemingly everywhere on TV lately, appearances in this industry can be deceiving. “I haven’t worked in 2026 at all, and that’s scary, like, ‘But I have an Emmy; I don’t get to work now?’ ” Hiller says with a knowing laugh, adding that he’s at least had some voiceover opportunities. “It’s a rough time. It’s not like business be booming. It’s disheartening.” 

Once he won the Emmy, Hiller admits, “I felt like I would immediately get a new TV show.” As Hollywood wades through a fresh era of mergers and contraction, that has not happened. But bopping around different series, fighting for roles wherever they open up, is something Hiller is used to — and, to anyone watching his stuff lately, damn good at. “I’m a really good guest star — I wear what you want me to wear, I sit where you want me to sit, I don’t ask questions, I can take notes very well,” he says.

As for the drier periods — like right now? “I’m uniquely qualified for them because I have spent 30 years with the ebbs and the flows of a career,” he says. And, hey, at least now when new character descriptions come up, it’s less “hotel clerk,” more “murderer with a curling iron.” That’s hard-earned progress

This story first appeared in a June stand-alone issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.