Interview: Kaitlin Olson (‘Hacks’) on DJ’s Journey and Playing with Jean Smart and Hannah Einbinder

Kaitlin Olson is one of the funniest people on TV and people are taking notice. For 17 years she has starred in the criminally underseen cult favorite series It’s Always Sunny in Philadelphia, while also showing up in a wide range of film and television roles.

Outside of Philadelphia, Olson has also spent the last three years playing DJ Vance, the daughter of Jean Smart’s Deborah Vance on the Emmy Award-winning Max series, Hacks. As a guest actor who has appeared in about a third of the show’s episodes, she has made quite an impact, giving audiences a chance to see the woman and mother behind Deborah’s comedy superstar public persona. 

Olson was nominated for an Emmy for Outstanding Guest Actress in a Comedy Series for the second season premiere. In season three, Deborah’s career has hit a new stride while DJ, a recovering addict who never really grew up, has decided she is ready to settle down, start a family, and finally give herself all the things she never really got from her mother.

It was great fun to talk with Kaitlin Olson about her co-stars on Hacks and what makes DJ such a fascinating character to play.

Karen Peterson: We’ll talk some specifics in a minute, of course, but in general, how would you describe your experience working on Hacks?

Kaitlin Olson: Oh my gosh, my experience. It’s a dream, and I mean, I’m not saying that just because you’re asking me about it. I tell people who don’t ask me. Paul [W. Downs] and Jen [Statsky] and Lucia [Aniello] who created this show are so kind and so intelligent and so funny, and that to me is just a perfect combination. And they’re making a very smart, educated comedy drama and it’s so hard to do, and I think they’ve just written it beautifully. I think they’ve written my character beautifully. I’ve said it before, but it is very challenging to write in a tone that is both comedic and dramatic. I think it’s very hard to pull off, and they’ve done such a beautiful job of that.

And it’s just fun. They’re fun and kind. Jean Smart is fun and kind. Hannah [Einbinder]’s incredible. It’s just a lovely show to pop in and out of. It’s especially hard to be a guest star on somebody else’s show. You feel like you’re the new kid at school or a party you stumbled across that’s already been going on for hours, so it can be a little weird, and it’s not weird here at all. It’s just one big family. Everyone’s welcoming and collaborative and so talented. I can’t say enough about it.

KP: How often do you work on Hacks?

KO: We discussed it and I was really clear that I just love this show so much and I love this character so much and I’m such a perfectionist and I’m busy. So all of those things together, I was pretty clear that, look, I want to come in when you have a great idea for DJ and for a storyline for her character, and I want to be able to make sure that I can make that special, and so I’m always a quality over quantity kind of person, so one or two great episodes a season, I’m so proud to be able to do. And that way I think I can keep it fresh and fun and unique and special. I never want you to get sick of her.

KP: I think it’d be impossible to get sick of DJ, but…

KO: That’s pretty great.

KP: This season there are a couple of really big moments for you and Jean and for the relationship between DJ and Deborah, including an episode that a lot of people have been excited to talk to you about, The Roast [of Deborah Vance]. Can you talk about how that came about and what it was like to get to try your hand at standup comedy as DJ?

KO: So fun. I love how headstrong DJ is. I love how unqualified she is and how she just jumps head first into it anyway, refuses all common sense advice and professional advice. I find that so ballsy and so thrilling, and I love that she’s doing it because there’s a chip on her shoulder and she’s out to prove that she’s a capable grownup. Which, there’s just something so funny to me about a vulnerable person pretending they don’t care when they really, that’s all they care about, and just wanting to get her mom’s approval so badly and then just wanting to get back at her mom.

But in the process of getting back at her mom, having this real validation for herself and her ability to do something well, but also to have that realization that maybe she isn’t the problem after all in their relationship. It’s not that she’s not good enough, it’s that her mother has an addiction as well, I just thought it was so freeing for her. So it was just really fun to be able to start it off in such a vulnerable place, the roast at least. Because literally right before she’s about to get up on stage, she becomes the butt of the jokes and that wasn’t the deal. I just love how that catches her off guard, and she really could have crumbled at that point and she didn’t, and she pushed through and succeeded and learned about her mom in the process. I just thought it was such a triumph.

KP: It really is. And the way that that scene, you start off playing it very slowly getting into it and being a little unsure, and by the end it’s just like, maybe DJ’s going to be a new star. Maybe DJ’s found a new calling.

KO: That would be amazing. That, I would really love to see that, and I’d love to see it not go well if I’m being honest.

KP: It seems like that could be kind of on par for DJ.

KO: Yeah, yeah. Start taking her baby on the road.

KP: And that’s another big thing that’s happening in DJ’s life now. She’s kind of moving into family life, so can you talk about that journey for her?

KO: Yeah, I mean, I’m excited to see where that goes. I think having a baby is just such a life changer, as everyone knows, but it opens up such a world of possibilities for someone who’s really basically a giant child herself. But I think it presents her with an opportunity to step up and break a generational cycle, and decide to be a good mom. Call on the things that she sees in her mother’s parenting that she doesn’t want to implement. Call on the qualities in Aunt Kathy (J. Smith-Cameron) that are kind and nurturing and loving. Or maybe she’ll blow it, which is also really funny and also very human. I blow it on a daily basis over here and I’ve got two of them. But yeah, I just think it’s going to be fun to see what happens with a giant baby having a baby and how she steps up or doesn’t.

KP: What is some advice that you, having had experience as a mom, would you give to DJ?

KO: Well, specific to DJ, I would encourage her to just trust her instincts. And everyone’s going to give her advice, including her mom. I think in her case in particular, everyone’s going to probably tell her how she’s doing it wrong or doesn’t know how to do it, but nobody knows how to do it. So it’s just such a trial and error kind of thing and then you just got to forgive yourself over and over and over and over and over.

KP: You brought up Aunt Kathy, so we did get to finally meet Aunt Kathy this season, played by J. Smith-Cameron. Can you talk about working with J.?

KO: Yeah, she is a doll. One of the sweetest, gentlest people I’ve ever met in life. She was so kind, and I’ve just been such a huge fan of hers for so long. I think she’s so incredibly talented and it was fun to see her play this very kind, soft character that still is there to stand up for herself, but to try and reconcile and to try and support DJ. Yeah, what a sweetheart. She is just… Again, I haven’t worked with a person on that show who isn’t incredibly talented and incredibly kind and really happy to be there, and that’s just so nice.

KP: It seems like such an amazing show to be part of.

KO: Yeah, it really is. It just feels really special. I think everybody just feels really grateful to have an opportunity to work on a show that’s this special.

KP: Last season you were nominated for an Emmy. How did it feel to have your work recognized in that way?

KO: That’s such a lovely question. It felt really good. It’s sort of a long running joke for us over in my other job that we don’t get nominated for Emmys 17 years in, and so it’s turned into something that just is what it is and it’s kind of funny. And we’ve always really talked about how we have our own validation and then we have our validation… We make each other laugh, and we have such wonderful, rabid fans that we feel validated all the time, anyway. But it turns out it feels really good to get nominated for an Emmy. Yeah, yeah, yeah. Surprisingly, it’s really quite a lovely feeling. I’m enjoying it. I wouldn’t mind doing it again.

KP: Well, hopefully you will get to do that in just a few weeks, so we’ll see.

KO: Fingers crossed.

KP: Over the course of three seasons now, we’ve seen DJ go from just a mess to someone who’s still a little bit of a mess, but seems like she’s really on the verge of turning things around and growing up finally. So what is something that you, Kaitlin Olson, have learned from DJ and from her journey?

KO: Gosh, I love that question. I think DJ is such a fighter and I love that she’s never given up. There have been so many opportunities for her to accept that she’s just a piece of shit that’s unlovable, because that’s the story that she’s telling herself because of the relationship with her mother. And she just keeps trying, and whether that’s to impress her mom or not, the fact that she just keeps showing up with full confidence is very admirable. Not something that I personally am able to always do. But just having nothing to back it up but to walk into a room being 100% confident and just blow it all out, I’m very impressed with her for that.

Season 3 of Hacks is available to stream on Max.

Kaitlin Olson is Emmy eligible in the category of Guest Actress in a Comedy Series for Hacks.