On ‘Hacks,’ the Joke Is on Kaitlin Olson. She’s Just Fine With That (2024)

There’s something so sad about the way Kaitlin Olson tries to spin a certain profane jab into a catchphrase in this week’s new Hacks episode, “The Roast of Deborah Vance”—and so strangely triumphant at the end of it, when she actually pulls it off: “What a c*nt!” Portraying the neglected and at times desperately needy daughter of Jean Smart’s legendary Vegas comic, Olson has always seemed like a natural fit for the role, having spent most of her career breathing furious, painfully funny life into women on the verge. (She received an Emmy nod for her performance last season.) But as Olson’s DJ nervously prepares to burn her famous mother before a live audience, she gets to show what’s underneath DJ’s despair. She’s still a riot, but she gets to break your heart a little too.

For fans of Olson, it’s no surprise to see her find those nuances. The Groundlings alum made a name for herself in the early 2000s with sharp improv work on sitcoms like Curb Your Enthusiasm and The Drew Carey Show, then a defining role as “Sweet” Dee Reynolds on the ruthlessly funny It’s Always Sunny in Philadelphia—which remains on the air, with season 17 on the way. She’s currently in production on a new network TV vehicle (ABC’s High Potential), having already led Fox’s The Mick, and has more juicy Hacks material on the way, with DJ newly pregnant and her mother starting to think about healing some old family wounds.

As ever, for Olson, there’s a lot going on. In an exclusive chat with Vanity Fair, we begin with “The Roast of Deborah Vance.”

Vanity Fair: As a fan of your work for a long time, I’m wondering, to start, how it has felt to play notes that are a little deeper, as they are in this episode. You’re mostly known for broader comedy than what you get to do on Hacks.

Kaitlin Olson: It’s great, if not just for the sheer boredom of it all—of just doing the same thing over and over. [Laughs] I love playing characters who are loud and nuts and mean and irrational. I don’t ever want to stop, but it’s fun to mix it up. Everything that goes into desperately trying to get the attention of the one person in your life that matters the most can be hilarious and totally heartbreaking.

You star in a recurring capacity here, so I assume you know you’re going to be in a set number of episodes. What do those preliminary conversations look like with the producers of Hacks?

The collaboration I’ve created with Paul [W. Downs] and Jen [Statsky] and Lucia [Aniello] is so lovely, because I said from the beginning, “I love your show so much that I don’t want to be in a whole bunch of episodes where I’m just in the background. If I show up, I want to be able to contribute something special.” So when they told me about this episode, I was like, “Yeah, that’s what I’m talking about.” I knew that my character was going to be pregnant this year, which was awesome. That brings in so many more layers to a person. So I just kept talking to them about what it was that they were looking for and what I was going to be able to contribute. It feels collaborative, and it’s not always like that.

I know you came from an improv background. Have you ever done stand-up?

Once. In my 20s. It was a disaster. An absolute disaster. Public speaking and stand-up comedy—you would think I’ve never been on a stage before. I hate it. I do not like being myself in front of people, I like being a character. Have a ton of respect for people who are good at it. But no, thank you. Not interested.

So this was a little bit of redemption, then.

Correct, that’s right. I got to pretend, and now probably I’ll nail it the next time I give it a shot.

You just needed a catchphrase.

And it should probably always be “what a c*nt!” because it was just a giant hit. [Laughs]

What you were saying about DJ, that balance of hilarious and heartbreak, extends to pretty much every scene you have with Jean Smart. It’s a fascinating dynamic. How have you found working with her over the years?

Jean and I hit it off immediately. There’s something, I don’t know exactly what it is, but you can tell when you are in a scene with a person who is trained in theater. She doesn’t bring one or two or three notes to a character. In every scene, there is so much going on, and I’ve been thinking about like, well, what is that? She’s just so good. She’s always in it. There’s never any dipping in and out. She’s just in it the whole time. And when you stay in it like that, you can find so many more little gems. I feel like in each take we’re giving and receiving different things, so when it’s cut together, she’s so funny and so kind and such a giving scene partner. That’s not always true with the lead of a show.

On my second episode, she’d be in a scene and she’d exit the scene, but the scene kept going and I was in it—and I realized she was running back and watching the monitors and what I was doing, and just so delighted. It’s always nice to feel appreciated, but when Jean Smart is running to the monitor and being so excited and wanting to see what I’m doing, that really elevates everyone’s performance. It’s that “never meet your heroes” thing. You can meet her. She’s fine. Go ahead and meet her. [Laughs]

To go back to what you were saying about knowing what to ask the creators for: You have a history of advocating for yourself along those lines in this business, even from pretty early on with Sunny. Where do you think that comes from? How has it evolved?

Well, it wasn’t from the beginning of my career, and I think that’s how I knew. I spent all of my childhood and most of my life really wanting to please people. I made a mental note of what you can and can’t say in school, or the popular girls won’t like you. That was the kind of kid that I was. I was not really speaking up for myself. I always knew that there was a thing that I was really good at, and people thought I was crazy in my little tiny town in Oregon to move to Los Angeles and think that I could be a TV star. Everyone made fun of me, including some of my distant family: “You’re going to what?”

All of those chips that get put on your shoulder give you so much motivation. I was like, “Oh, they don’t get it.” But I did get it. I believe in taking baby steps to speaking up for yourself. And also—this is important too—when I first started, actors didn’t improvise anything. In fact, if you switched a line up accidentally, they’d cut and go back so you could get it exactly perfect.

You were on The Drew Carey Show for a few episodes early on, which I’d guess was tightly scripted.

I was only supposed to do one episode, and I had this big monologue and it was in front of a live studio audience. I’m very comfortable in front of big audiences, way more than I am in front of one person. Auditions are terrible for me. I don’t want to perform for one person. But because that was filmed for an audience, I started doing different things with it, getting the gist of the monologue but saying it in my own words. There was a part of me that was like, “Ugh, I’m going to get in trouble.” But people were laughing. It was working, and I think that validation starts to grow on itself. That helps you be a little bit braver.

Your first-ever TV role was Curb Your Enthusiasm. When you were talking about watching Jean get invested in your performance, I thought about the feeling of making Larry David laugh at the very beginning of your career.

Oh my God, that’s a perfect example. In my audition for Curb Your Enthusiasm, the more I would yell at him, the more he would laugh, and I was completely filled up inside. That’s all you need. Especially on a show where there’s no script, if he’s laughing at you, he’s laughing at what you are coming up with. So that’s just an even bigger honor.

If I’m putting myself in the shoes of an actor in her mid-20s who’s up for a lead role, and the role is not all the way there, I would feel very nervous about expressing any hesitancy. But with Sunny, you didn’t.

Well, Sunny was a really happy accident. That audition was incredible, because the sides weren’t for Dee. [Laughs] They changed a scene that was between Dennis and Charlie because they didn’t have any funny Dee scenes, so they gave me that. But I didn’t know that. So obviously for the audition, they changed the name. And it was funny! I loved it, I did it, and then Rob [McElhenney] said, “Go ahead and put the sides down and we’re going to do the same scene, but say whatever you want. Same scene, but say whatever you want.” No one had ever done that before, and I was like, “What?” It was the most fun audition I ever had. I got in the car and was like, “I mean, that’s my role. I believe I got that.”

It was only later after they asked me to do it on the phone, I didn’t have to talk to their faces. I just told my agent when they were like, “Oh, that wouldn’t be your character. Here are five scripts that are written, and here’s the Dee character.” And it wasn’t good. So I passed. Then Rob called me and was like, “That’s not what we meant. We do want you to be you.”

And you’re still doing it, 20 years later.

Yeah. If I had gotten an audition and they had literally just pulled a Dee scene out of the scripts that they had already written, I probably would’ve passed on the audition. I was coming off of a show that was shot in England where I had a bad experience, and I said, “Okay, for the rest of my life, I will never take a job for money or just because I want to be on TV.” I would’ve missed out on the whole thing if I got an actual Dee script.

From there, of course, you get to play an iconic character. Has it felt frustrating to be so defined by Dee? How have you worked with that?

Every script I’ve been offered since Dee, it’s all versions of that character. But I don’t find it annoying. I’m really good at emasculating men, and that’s really quite an honor. [Laughs] But no, I definitely got very typecast. I will say, when John and Dave Chernin wrote The Mick and they described it to me, I was like, “That sounds so funny,” but I was being offered a similar character. I read the script and was like “Ugh, damn it, I love the script. I want to do it, but I’ve got to find a way to make it not Sweet Dee.” We did our best with that. Generally, yeah, I very actively try and take roles that are different so I can do something else. I still get to do Dee, so I’m not really giving one up for another.

I was going to say, she’s always there.

Always going to be there, into her 90s. I’ve decided we’re going to do that show.

Is that a comfort? Does it still feel fresh to do it every year?

It’s a huge comfort. I’m happy every single day I go to work. I’m working with people I find to be at the absolute top of their game. I’m so well taken care of. My showrunner knows what he’s doing. I also happen to be married to him. It really does allow you to go off and experiment and try new things, because I still always have that to come back to. Now we do eight episodes a season; it’s a six to eight week commitment. It’s a no-brainer.

I loved when you guys reunited at the Emmys this year. There was an implicit statement there that was then made explicit about never having been invited as nominees. But by this point, you had just become an Emmy nominee for other projects, including Hacks, and Rob won that year for his reality series Welcome to Wrexham.

Right, we were fine to show up. [Laughs] We’re not bitter! I mean, we joke about it now. Now we’re like, “Oh God, what are we going to do if we do get nominated? We can’t have this decades-long joke anymore.”

Why do you think awards recognition never happened?

We talk about that a lot. I think there are some shows where it’s just decided, “Oh, this is the hit show of the season,” and people will give it a shot. And then there are just some shows that are just like, “No, this isn’t an Emmy show.” And if you jumped in and saw a clip of our show and didn’t quite understand it, you’d think this show is raunchy and gross—not appropriate and not classy and lowbrow. And the truth is, that’s true. And if you really watch a full episode, it’s so smart. We’re making lots of statements. We are making fun of extremists. It’s a lot more intelligent than people think.

It just became a thing where it was like, “Oh, that show again.” People are looking at new shows. The truth is we are getting a lot of validation every single day. We have fans that will cry and shake if they take a picture [with us]. We’re doing what we want to do, making a show that we’re proud of and making people happy. I really am truly good. But will I take an Emmy? Yeah, I’ll take an Emmy.

Hacks, by contrast, has a real machine around it in that regard. And you’re a part of that, even as a recurring guest star.

Sunny seems like the thing that I did when I was a kid and happened to keep doing, and now I feel like, “Oh, now I’m an adult and I’m in the adult shows with the adult parts and the adult publicity and attention.” It’s quite a thing. Hacks is one of those shows where it’s just been decided like, “You have to watch Hacks.” It’s word of mouth, it’s everywhere. I feel like I have the best of both worlds. I’ve got my little underground thing that I’m proud of, and I’ve got this thing that I’m so happy to be a part of because it’s just so good and so popular.

In terms of guest roles, you’ve only done an episode of Space Force since recurring on New Girl. Are you saying no a lot?

Yeah. I’m just too much of a perfectionist. I want to be the best part. That’s hard when you’ve got Jean Smart and Hannah Einbinder. You know what I mean? That sounded really sh*tty. [Laughs] I didn’t exactly mean that, but yeah, I just, I’m a quality over quantity kind of gal.

I love this quote of yours: You’ve said you “feel attracted to playing broken people.”

Yeah… [Laughs]

Where do you think that comes from?

It’s funnier to just be broken and torn apart and having to build yourself back up. I’m a very sensitive person. I had an amazing childhood with my family, but a very hard childhood with friends and girls who were really mean because I was really nice—looking back, you’ve got to laugh at it or you’ll cry. I got in a horrific bike accident, which I’ve talked about a million times, but going into junior high school with a shaved head with a giant circle on the top and a busted face, it was—I didn’t ever have a boyfriend, girls didn’t want to be friends with me. It was tragic, and it’s the best thing that ever happened to me. My life could have been so boring and normal.

Almost dying is so fun. [Laughs] I know. It builds character and it forced me to be funny because I wasn’t getting through middle school and high school relying on my looks. Which sounds very vain and surface, but that’s what kids do. That’s just part of being a middle schooler. You just want to fit in. I had to figure out another way to be happy. I just figured I’d laugh at myself.

This interview has been edited and condensed. This story has been updated.

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