If Jeff Hiller’s In It, We’ll Be Watching

All month long, Bustle’s annual The Entertainers Issue is celebrating the performers and creators who lit up our screens and beyond in 2026.

Taylor Swift wasn’t the only one dropping Easter eggs the night of the Emmys. Jeff Hiller got to make a nod to one of his past characters during host Mariska Hargitay’s celebrity-filled opening segment. “This was my seventh flight attendant, so it felt perfect,” Hiller says. “I said, ‘Make his name be Stewart, because on an episode of 30 Rock, my character’s name was Stewart the stewardess.”

The actor and comedian has come a long way since his bit parts on 30 Rock. After years of guesting on many beloved sitcoms (Unbreakable Kimmy Schmidt, Broad City), Hiller began a regular role on HBO’s acclaimed dramedy Somebody Somewhere in 2022. At the end of its three-season run, he won an Emmy for Outstanding Supporting Actor in a Comedy Series for his performance as Joel, the devoted best friend of the show’s main character, Sam (Bridget Everett).

He followed up the win — and the release of his memoir, Actress of a Certain Age — by acting on two of the buzziest shows on TV. With just seven minutes of screen time, he earned another Emmy nomination for his guest role on Pluribus, the twisty sci-fi thriller from the creator of Breaking Bad. “With Pluribus, where I was playing this hive mind person, and you’re supposed to be a little bit removed, I’ve always just tried to make everything be really specific and really present,” he says, adding with a laugh: “And then also, you know, just be charming.”

Hiller, 50, brings that same charm to Widow’s Bay — another big winner at this year’s Emmys — as town hall employee Dale. Hiller is a longtime friend of the show’s creator, Katie Dippold, and their bond led to his hysterical standout scene in the finale, when Dale bursts into the underground shelter with a screaming warning right after his coworker Patricia (Kate O’Flynn) calmed the room down.

“When we would do improv, [Katie] always would make me do scenes where I was, like, freaking out because she likes the way I freak out — and in fact, she loves how I react to scary movies and haunted houses,” says Hiller (who’s headed Off-Broadway next to star in the new play The Exhibitionist). “I think she wanted me to react in the same way to this scary island, and that’s all the prep that went into it. I was like, ‘I know what you want, Katie.’”

While Hiller’s turn on Widow’s Bay was small, it will only get bigger in Season 2. “Dale will have a lot more to do. But what? I have no idea. They haven’t told me. I’m not being coy,” he says. In fact, there’s still a lot we don’t know about Dale: “I don’t even know if he’s gay. I mean, he’s probably gay, right? I don’t know if he was born on the island or if he can leave the island. I don’t know if he’s got a special someone or if he lives alone with his mom, so I’m just really anxious to find out all that information. And if he happens to have someone in his basement locked up, all the better.”

On having resilience as an actor:

It’s the only thing I’ve ever really wanted to do passionately. Even when it got bad, it was never so bad that the idea of a job in an office seemed better. Even though there were times that were very lean on money, and times when I had to do awful jobs to make ends meet, it was still worth it to have that hope of being able to be a full-time performer.

Now that I am a full-time performer and don’t have to have a day job, the gratitude is off the charts. If I had been famous at 22, I would not realize how lucky and amazing this life is. So the fact that I didn’t get to be full-time as a performer until my late 40s, I really appreciate it because the idea of making an Excel spreadsheet — how awful!

On how he got his Widow’s Bay role:

I submitted a self-tape, and Katie was like, “I saw your tape. Why didn’t you just tell me you were gonna audition?” I was like, “I don’t want to be weird or whatever.” And she’s like, “Look, you can totally do it. This role that you auditioned for is very small. He’s going to die, and so if you want to do it, you can.” And I was like, “OK.”

So, I started shooting, and they just started adding little things for me to do. If you think that role is small, it was so much smaller before. I didn’t even have a line in the pilot, but we did a reshoot, and they gave me another line. Then they said, “We’re not going to kill you off.”

On how life changed after winning an Emmy:

Career-wise, I guess I’m a regular on Widow’s Bay now, but I almost feel like that might have happened even without the Emmy because they seemed to like what I was doing and they kept adding me into more bits. I do think [being featured on] the poster is just from the Emmy.

Before the Emmy, when I would show up on set, people would be like, “OK, you’re No. 24, and this is your room. Go away.” And now people know that my name is Jeff, and that’s nice.

On Somebody Somewhere’s legacy:

What’s funny is that a lot of people have said, “I didn’t know who you were until Widow’s Bay, and then I found your book, and then I found Somebody Somewhere.” And I’m like, “Wow, you found Somebody Somewhere in the weirdest way possible because it couldn’t be more different than Widow’s Bay.” But these people who found me via this wacky, terrifying show have come to me and said that when they realized Season 3 [of Somebody Somewhere] was the end, they felt like they lost a friend because they can’t go back and visit Sam and Joel, which is so sweet and gratifying.

Murray Hill’s presence was so important for trans visibility on a show set in the Midwest. You see Kansas pass this ridiculously anti-trans bill, but there are still trans people in that state. There are still queer people in that state. To show these queer folks living a life that still has joy is weirdly like a protest: You can try to kill our spirit, but you never will. And people have said that [about the show], and they often say thank you. Nobody’s saying thank you for being the guy in the Glee Club on Community.

On predicting the next Oh, Mary! star:

I love predicting who the next Mary in Oh, Mary! will be. I did predict Bowen Yang. I want to say I did not predict Maya Rudolph. I thought that one was amazing. I certainly didn’t predict Betty Gilpin, either, and I thought she was so good. I met Betty [who also appears on Widow’s Bay] at the Emmys, and that was exciting.

I was gonna say Amy Sedaris — I feel like it’s not gonna happen, but it’d be really fun to have Amy. And then after that, it’s going to be somebody really weird, like Kate McKinnon. I don’t know why — I’m just guessing her.

On what he’s manifesting next in his career:

Well, this isn’t a very exciting answer, but surprise! I’m manifesting a surprise for the next thing. I could never have predicted Widow’s Bay or Pluribus. The idea of getting a second Emmy nomination — I never would have predicted that. But the surprise is the best part about this job. It’s never predictable. So maybe it’s a show on Broadway. Maybe it’s a show I write. Maybe it’s a movie that I get to be in, or maybe I get to be, like, someone who kicks ass. Wouldn’t you be shocked by that? Wouldn’t that be fun?