From Bit Parts to Two Emmy Nods: Jeff Hiller’s Long Road to Success

20:14Kara Swisher:Quince.com slash cara.

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22:06Kara Swisher:A Gruen's pack also contains 6 grams of prebiotic fiber. To help you visualize it, that's equivalent to more than 2 cups of broccoli. Gruen's ingredients are backed by over 35 ,000 research publications. You can't fit the amount of nutrients Gruens does into one daily gummy, which is why it comes in a pack. Save 52 % off with the code CARA at Gruens.co. That's code CARA, K-A-R-A-G-R-U-N-S dot C-O. Let's talk a little bit about the industry and your break in it. Before your recent successes, you had a lot of bit parts. It's sort of the stereotypical sassy gay man. In your memoir that came out last year, you write, quote, If you're obviously gay but not hot, your roles are limited.

22:50Kara Swisher:You just play the bitchy gay. Now you have a more established career in Emmy. Talk a little bit about this because I assume you get more range now or perhaps not. Somewhat, yeah. I think I get to audition for things that I wouldn't have been able to audition for before. But I think, you know, at the end of the day, I look like I look. and you can't plug me into just anything. Like, no one's going to cast me as a romantic lead. And I don't need to play the romantic lead. A lot of times those are really boring parts. But, you know, it takes a while to convince other people that you would successfully play something that you haven't successfully played previously.

23:37Kara Swisher:Now, you told The Hollywood Reporter back in May that despite winning this Emmy last year, you hadn't worked at all in 2026. Is that still the case? I regret saying that. It makes me sound so pitiful. I was talking about the industry, not specifically about me, but that is still true, yes. No, a lot of friends of mine who are well-known have had a hard time. Yeah, it's just, you know, in all of these conglomerations that are merging with other conglomerations, I know that that's maybe up in the air now, but I just feel like, or, you know, the latest one, not all of them. But I think that there's just a lot less content happening, especially post-strike.

24:16I think people realize, like, the streaming method isn't really a way to make money, and so they don't know the way forward yet. And so that means just a lot less work. And I'm so grateful that Widows Bay got a second season and that hopefully they've written themselves into a corner to bring me back. But yeah, it's been surprisingly dry.

24:40Kara Swisher:Talk a little bit from an actor's point of view. I write a lot about the consolidation from a business point of view and where it's going. But what is it like for actors like yourself when you're looking at these? Right now, the big story is the Paramount, Warner Brothers, Discovery, Every federal judge did put it on hold. We'll see where it goes from there. But these are happening. These are happening. And then on top of that, there's AI that people are talking about. It hasn't really gone anywhere yet. So far, Tilly Narwood is not killing it. I love her, though. She's so great. She is. She's really good.

25:12She's so interesting.

25:13Kara Swisher:She's so interesting. How do you think about it as an actor now, just as a working actor? Because a lot of people hear from, you know, the studios or the production companies or what does Netflix think and this and that. How do you as an actor think about what's happening?

25:33I mean, just because it affects me, you know, rather directly, especially as someone who's, you know, you know, Nicole Kidman is probably okay. Yeah.

25:45Kara Swisher:She's still in the theater and no one will go with her in those ads, if you notice. It's heartbreaking. But it feels good in a place like that. I know. She's always alone in the thing. I was like, could you not have a friend that you can't take to? Anyway. She doesn't want anybody to distract from her sparkly suit. Right. That's true. It's true. She is kind of sad. And like, not even. Anyway, I once saw The Purge all by myself in a movie theater, and I thought, this is cool. That's a movie to go to alone, actually. I know. Exactly. Yeah. So I find it, you know, kind of scary. And when we were striking in 2023, you know, AI was a big part of that.

26:25And I worry because I think what you're saying right now is true. Like, it is very mid currently. I don't know that in the future people won't, you know, we eat Taco Bell. We're okay with mid.

26:39Kara Swisher:Right, right, right. That people won't accept it. You mean audiences. Yes, exactly. And, you know, that's a little scary. And, you know, kind of makes me feel like a coal miner or something where I'm like, oh, no, am I in this dying industry? Right, right. And when you look at the mergers, now, mergers have happened before. They've happened lots of times. But how does it actually impact working actors like yourself? What are you all talking about? Well, the big thing is that across the board, no matter if you have won an award or not, people are saying, there's no money. There's no money. We cannot pay you anything more than the bare minimum that the union says we're allowed to pay you.

27:26And a lot of times that bare minimum, you know, you can't support yourself on that because a lot of like character actors like myself, we're working three, four days a year. Not now, like now I have Woodrow's Bay or what have you, but like most of the time, three or four days of a year of work is good. It's like a great year for just normal actor. And you would often, if you got a commercial or something, that the residuals would last you for the entire year and you might not have to have a temp job for that year. And that's just not, that's just not a possibility at all. And on top of that, of course, I know I'm saying stuff that everybody's heard a million times, but like rent is so high.

28:09And we all have to live in these major cities where the rent is even higher than the rent in other cities. And so it just makes it so that you can't be, you can just never get ahead financially. You can never feel safe financially. And it's terrifying. I mean, like even just like pilot season, there used to be a pilot season. And even if you got a pilot and the pilot didn't get picked up, you made enough money from that pilot that you would be able to not work for a long time. And it's like you get six episodes and the next one we're going to film in two years. Where it used to be 22 episodes every year.

28:49Kara Swisher:Right. Yeah. It's funny that, you know, even winning an Emmy doesn't insulate you from this. But I have a lot of friends who won Emmys and they say the exact same thing. And you're sort of surprised. One of my friends just got a regular broadcast show, and she was like, it's 22 episodes. I don't know what to do, right? Rather than six. Six to eight. Dreamy. Dreamy. Sexy. Get yourself on Law & Order or one of those. I know. I want to. Yeah, you have to be. You'd be good as a quirky medicalist. I did play a computer tech on Law & Order Criminal Intent. Did you? Okay. Yeah, but I got cast, and I was a recurring role, but I got cast in the last season.

29:24Kara Swisher:Oh, the last one. I shot my first episode, and the next day they announced it was canceled. Right, right. Not all law and orders go to the moon. No, it's true. But we are very happy for Mariska. So we are. I love her. I know. She's great. I like your whole jam right now, what's happening with her. Me too. But you have talked about finding success in action later in your life in late 40s. It was the subhead of your memoir, Actress of a Certain Age, My 20-Year Trail to Overnight Success, which I love the title. Thank you. talk about that. Talk about what, and what advice would you give to someone who's in the same position you were in five or six years ago?

30:03Well, my advice is show business isn't fair. I definitely don't subscribe to the idea that if I did it, you can too. Like I got lucky. I got so lucky. I'm fully aware that I got lucky. And I often think like, if somebody's like, it's not worth it for me anymore. I want to quit. I'm like, I support you. Go get an apartment with laundry in it. How fun.

30:28Kara Swisher:HVAC. That's the way to go. You don't think there'll be robots doing that eventually or no? Eventually, but you'll be dead by that time. So don't worry about it. Okay, maybe I'll go get into HVAC. Yeah. So I think my advice would be two things. One, don't compare yourself to other actors because it always ends up crappy. And also you never know what's happening beyond the deadline article. And two, the other thing would be, even if you're not getting paid or getting awards, your art is just as valuable as anyone else's. Because I think for so often I felt like, oh, I wasn't a good actor because I wasn't full-time.

31:12And I think that's kind of bullshit.

31:14Kara Swisher:Yeah, I know. I know. I recently interviewed Marc Maron. He's talked about getting this big break later in life too, which was podcasting, in fact. He said he didn't think he'd be able to handle the fame if he found it earlier in his life. How do you think about that? I have heard him talk about that. And, you know, he also had to get sober and stuff like that. And I think I could have handled it fine. I'm pretty boring.

31:40Kara Swisher:But the big break you had was an HBO show, Somebody Somewhere, which is a wonderful show. You play Joel, a compassionate best friend to Bridget Everett's character, Sam. Last year, as we noted, you won the Emmy for Outstanding Supporting Actor in a Comedy Series. The show ended in 2024. But talk about that character of Joel and how you envisioned it. Because it's a very touching relationship. I mean, it's a relationship show, obviously, but that's the key relationship in it. Right. So when I got the role, when I read the pilot, I was so shocked because he talks about being involved in the church.

32:18and he talks about being obsessed with Bridget and about being like not very popular in high school. And I just kept thinking like, oh, this is just like me because I grew up in the church and I was obsessed with actual Bridget. And I remember I took this class from Marcy Phillips, who's the casting for ABC. And it was a class on how to become a series regular. And she was like, you need to find a role that's kind of like you. when I felt like, they don't write roles like me.

32:50Kara Swisher:Right, they don't. No, because this is a very specific middle-class life in a small Midwest town. It's about grief. It's about chosen family quite a bit. And they don't have fancy jobs or live in big modern houses. Joel drives an old Buick, the Sabre, and dreams of owning a Vitamix. Do you think Holly's moved away from telling those kind of stories? They used to be quite prevalent, if you think about it. Oh, you think? I feel like it's such an anomaly that we even got that show on the air. Well, Roseanne, there was a bunch before she lost her mind. Yeah, there was a bunch. I guess there's Roseanne, yeah, and like The Middle and things like that.

33:24That's true. They were all very much family sitcoms. And I don't know of any other show that's so focused on Chosen Family as this one is.

33:33Kara Swisher:Well, you'd have to say Friends, even if you don't like that show. Oh, I guess you're right. That is kind of about Chosen Family, isn't it? Yeah, it's a bunch of straight people in New York with a fantastic apartment, but that's different. but it's still just. Let's face it, what this show really did that was different is it cast fuggos, right? It cast people that aren't gorgeous. Okay. And I think it was so rare that they did that and it's, they definitely aren't doing it now. I know that for a fact. Yeah. And I think it's just, that's kind of, there's like a, I was going to say there's a beauty in that.

34:08But there is. There's like a

34:13representation matters. And it's nice to see people who aren't a double zero and have, you know.

34:21Kara Swisher:Yeah, and they're solidly middle class. They're not, and they're not rich. They're not rich. They're not, yeah, and their problems are relatable. And in the same way that like people, I mean, people love Widow's Bay and Clorobus way more than they loved somebody somewhere. But I think in the same way that, like, seeing this world that is so different than ours is kind of a relief, I think there is also a truth in seeing a world that is attainable. Right. Is actually a really beautiful thing to be able to see and have. Yeah. The show also challenges viewers' expectations of what life in the rural Midwest can look like, right?

34:59Kara Swisher:We have images of that that are probably out of date. Joel is an out gay man who goes to church and is surrounded by other queer people and straight people who love him. It's really interesting to, as you say, someone like yourself. It does challenge our perceptions of what people's lives are like. I mean, I have a cousin who lives in a rural area and goes to church. He's gay. You know what I mean? A very similar kind of. Yeah. I see. And that was my thing, too, is like I knew that person so well. Even if I wasn't exactly that person, guys, I don't go to church every Sunday and I don't live in the Midwest.

35:34I live in New York City. But I still, I knew, I don't know, 10 versions of that person from my time growing up in Texas. And I went to school at a Lutheran college in Seguin, Texas. And I knew so many out or like, you know, glass closet out gay folks, both men and women who found their community in their church. but I'd never seen it portrayed in media, ever. Not even in a novel. And it also, it wasn't playing it like his Christianity was a joke and it didn't just fall into this idea of what the news paints Christians as in general, which there are definitely those people who are sort of right-winging, but it's clear that Joel is a part of a progressive church.

36:24They're handing out toiletry kits in one episode. They're blessing animals in another one. This is not the easy depiction of a church that's just, you know, kill the gays.

36:39Kara Swisher:Right, yeah. And it also challenges the idea that all gay people who live outside of cities live in fear and in the closet. Right. Which is interesting. I was just this week in Traverse City visiting Pete Buttigieg and Chaston. Wow. Yeah, it was interesting. Of course, they just had a very terrible thing happen to them around their kids. But it was really interesting. And I was like, why do you live here? Like, why aren't you in, where'd you go? You know what I mean? It was really, and they were sort of like, Kara, oh, that's not being an asshole, Kara, essentially. But it was, you know, they love it there because they have kids and it's better for kids and they have family around them.

37:14Kara Swisher:And they definitely deal with, you know, a lot of things they don't love there. At the same time, they have a lot of support too. And so it's sort of this, you know, One would assume the minute you step off a plane and somewhere like that, you're going to get a very different, or fearful as a gay person. Right, and I think that, I don't think the show was trying to say that there's never microaggressions or certainly misgendering happens all the time, but that happens all the time in New York for Murray. So, yeah, but I do think, because so many, when I would do press for it, people would be like, Tell us about this fantasy, this fantasy of queer people in Kansas.

37:58And we went to Kansas. Bridget's actually from Manhattan, Kansas. And we went there and we met, I mean, you know, we met a lot of mostly straight folks. But there were like a lot of queer folks that came out. And, you know, of course, they came out specifically for the queer show. But there are even like a shop that's owned there by a trans man. And I guess what I'm trying to say is that is the case. People live where people live.

38:30Kara Swisher:We'll be back in a minute.

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41:31Kara Swisher:I wanted Zero in a little bit to talk about faith in the church, Because in your memoir, you write really beautifully about church and growing up in it. It was a place of belonging for you and an escape from bullying you experienced in school. You even considered becoming a pastor, which was really interesting. You still can, by the way. This Emmy thing doesn't work out. HVAC or pastor? One of the two. HVAC is probably better. Although you'd make more money with HVACs. Your relation with religion got more complicated as you got older and came out and you no longer tanned. And talk a little bit about that, because that was a thing of moving part of the book, I found.

42:08Kara Swisher:I grew up Catholic, and I haven't been in a Catholic church since I was confirmed, which I did for my grandmother. But now with this new pope, I'm like, I kind of like it. I know. It draws you in, in a way. Talk a little bit about your views and how you think about it now. Well, see, when I was growing up, the church was the place that helped poor people, specifically poor people. And it was all about, it was about helping people. It wasn't just poor people, I guess, but it was about helping people who were in need. It was a huge part of it. Like the first and foremost part of it. It wasn't about rules or saying you're living in a way that is not right.

42:50It was about helping people. We had the food bank. We had the clothing bank. There was a rental assistance program there. And so for me, when I hear church, I think there are so many folks that hear church and they're like, I don't want to have any part of that. But because I grew up in this slightly progressive church, I think of it as community. And I think of it as being beautifully sacrificial and helpful and kindness. And so I don't have those negative associations with church that a lot of people do. And like you said, this new pope, even the last pope was pretty good, too. Yeah, he was.

43:34He's a pre-pope for this pope. Pre-pope. American pope, making everything cool. Right, yeah. But I also feel, you know, I used to know all of these really cool progressive nuns, too. And I worked, I did, after college, I did this, I called it a Christian commune. And that's a little tongue-in-cheek. But where we were actively, you know, boots on the ground, helping folks. And that is the church I choose to believe in, that actively helps people and is good for the world, rather than just this current church that gets all the press that's about, like, just, I don't know, hating on people. Just period.

44:18I was going to say, I was going to list some people, but there's a lot of people.

44:20Kara Swisher:They're focused on James Tallarico this week. Right. That's true. That particular branch of the church. It's true. It's going to lead you into whatever, women's bathrooms or something. I'm fascinated by how they're using trans and gender. But that said, we're seeing young people return to the church in ways. My son started going to church. I never brought him into a church ever. Wow. Catholic. Really? Yeah, he's now going to Eastern Orthodox now. I'm like, no, we're not doing this. We're not doing this. You know, the food is excellent during the festivals, but no. But he can do what he wants. They have a lot of gold leaf in there.

44:58It's pretty. Do they?

45:00Kara Swisher:I told him I'd go to a service with him. But I think it's community is what he's looking for. Yeah. And the positive role that faith can play in a person's life. Because we talk a lot about that. And queer people have been building church-like communities forever. It's one of the plot points in somebody somewhere, actually. but historically we're born out of exclusion from mainstream society. How do you look at it now and how do you create spaces without asking people to be someone they're not? Well, God, I don't know. It's a great question. I don't know if I have a good answer. I think, well, first of all, I'm not, the one way I'm really not like Joel is I'm not someone who creates spaces for people.

45:41I'm a joiner, not a leader, hardcore. for. But I do think what I have a gift for is I listen. I listen a lot more than I think most, I was going to say most actors, but I think most people, I think I listen more than most people. And I think that is a gift for creating community is acknowledging the other members of the community. The bar is low.

46:06Kara Swisher:Yeah. Yeah. Are you interested in this push towards the church, you know, the belonging the church can provide and creating those spaces. I mean, I get it. Like I said, it's all about community. And I think community is absolutely necessary. And I think that, I think you just have to be careful that you're finding your community in a space that supports you rather than hurts you. And because I do feel like I could totally fall for a cult. I have to really be on the lookout for that. I think all successful sitcoms are about a family, creating a community. At Widows' Bay, you have your group of weirdos, just like The Office, or something like that, where there's something like that.

46:51And you're right. You're right. It is all about finding family. And that's what I think probably life is kind of about, right?

46:56Kara Swisher:Yeah, in a lot of ways. So every episode, we get a question from an outside expert. Here is yours. Hi, I'm Allie Wentworth. And I first met Jeff Hiller when I cast him in my show Nightcap, and he was brilliant. Jeff is the warmest, most insightful, optimistic human being I've ever met. So my question for you, Jeff, is what keeps you up at night? It could be macro, like what's happening around the world. It could be micro, like you have too many mice in your apartment. But what causes Jeff Hiller insomnia? Mice in my apartment? Come on, Allie.

47:39I mean, I think it depends on the night. But I will say, I sleep pretty well. Yeah, okay. I'm pretty good at sleeping. I will say last night, I was up worried about my sister because my sister just had to put her dog down. And I couldn't sleep thinking about that. And I think that's probably, I think if we say macro or micro, I think I do tend to focus on individuals and people hurting. I will, I'm constantly thinking about children in Iran and Palestine and children in war zones, children or in, I just, I don't know why I'm not worried about the old ladies. I guess I'm worried about them too, but I just think, I do think about kids all the time who are, just by bad luck of being born in a place that's full of turmoil, I think about that a lot.

48:39Kara Swisher:That is a worthy thing to worry about. That is a worthy thing to worry about. I mean, but what does worry get you? You got to start doing stuff, right? Well, no. Worry's okay. It's okay to be just worried. Yeah, yeah. Yeah, it means you're alive, actually. That's deep, actually. Yeah, thank you. That's good. So, yeah, I sleep well, too, oddly enough. I'm like, I'll deal with it tomorrow. Yeah, that is sort of what I... Yeah, I'm always like, that asshole, I'm going to go to sleep now. I recently interviewed the Let Them lady, Mel Robbins. Oh, yeah. You know her, Let Them. But she has an out. She has Let Me, which I have to point out to people.

49:19Kara Swisher:She doesn't let them. She lets me. Wait, but do you think that the, are you saying? I think she's saying let them and it's very appealing. It's like, yes, I'll let it go. But then she has a thing that says let me, which is what is my action going to be. I see. You see, it's an out because let them be an asshole, but let me take a stick and hit them. You see what I mean? So it's the same thing. You're not really letting them, are you? So anyway. That's really where you went, huh? Yeah. Oh, that's interesting. That's not where I would go. No, really. interesting. We'd seek some a lesbian. This is the problem.

49:54Kara Swisher:I'm Carol. I'm Carol on You're Carol. You're right. And I'm Larry. Yeah. Yeah. Atom bomb. Atom bomb. We're going to be doing the atom bomb. Anyway, let's not end on that. Kara's blowing up the world. Because I know, I also want to know, my last question, what gives you hope? Because you are a hopeful person and you play hopeful characters. You really do. They're always sort of looking on the right side of things. It's from you, presumably. It's also from the writers, obviously, but you get picked for those roles. And I do talk a lot on the show about the need for people to find hope right now, because a lot of it can feel overwhelming.

50:29Kara Swisher:So I'd like to end by asking you, what, you know, gives you hope right now? This is sort of a controversial answer, because I think a lot of people don't find hope in this, but I find that the younger generation, the folks that I'm interacting with, every older generation, because like when I'm Gen X and I remember all of the like slacker on the cover of Time and all that business. And so every generation gets shit from the previous one. But I just keep finding young people who don't want to put up with people who are hoarding wealth and who are not down with being loose with their language, who are wanting to be respectful of people.

51:16And I find that to be hopeful for the future.

51:19Kara Swisher:I would agree with you, with young people. I have a lot of kids, and two of my older kids are like that. And everyone's like, are you overwhelmed? I'm like, no, because of them, not because of you. Not you in particular, but whoever I'm talking to. You people 25 to 50 need to go away and let the people under 25 run everything because it's a very exciting time for them in a lot of ways. Yeah. The way they're voting, the way they're talking about things, and the politicians they're attracted to also is really interesting. It's giving everyone else the rash, but I find it very hopeful in some ways.

51:54Me too.

51:55Kara Swisher:Yeah, absolutely. Anyway, keep doing your wonderful characters. I'm excited for Dale to have a big role. Me too. I think you and – wait, what's her name? Dale, also Dale, right? Yes, Dale Dickey. She plays, what's her character's name? Rosemary. Rosemary, which is a great name, by the way. But I hope you two have a spinoff. That was my whole goal, is the two of you have a spinoff in some way. Dreamy, I'm down. Like you get on a boat and start, like wander to another island in some fashion. Start our own island cult. Start your own island. She'll lead, I'll follow. Misfit toys, you know, island of Misfit, which were, in fact, all the gay characters and all those kids things, if you think about it.

52:29It's true, I saw that little swoop.

52:31Kara Swisher:Yes, yes, yeah, exactly. But good luck with next season. and amazing job. Thank you.

52:41Kara Swisher:Today's show was produced by Michelle Alloy, Catherine Millsop, Madeline LaPlante-Duby, Megan Burney, and Kaylin Lynch. Nishat Kerwa is Vox Media's executive producer of podcasts. Special thanks to Catherine Barner, Dave Shaw, and Julia Sharp-Levine. Our engineers are Fernando Arruda and Rick Kwan, and our theme music is by Trackademics. If you're already following this show, you're sleeping well. If not, you're eating Taco Bell and you're okay with mid. Go wherever you listen to podcasts, search for On with Kara Swisher and hit follow. Thanks for listening to On with Kara Swisher from Podium Media, New York Magazine, the Vox Media Podcast Network, and us.

53:16Kara Swisher:We'll be back on Thursday with more.

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