Kaitlin Olson Shares Her ‘Bittersweet’ Goodbye to ‘Hacks’ After That Full-Circle Send-Off With Jean Smart

“I don’t care about anyone else — I just want to make Jean laugh,” Olson tells TheWrap

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Kaitlin Olson in "Hacks" Season 4 (HBO Max)

Note: This story contains spoilers from “Hacks” Season 5, Episode 5.

As “Hacks” prepares to close out its five-season run this spring, the HBO Max comedy crafted a special sendoff for Kaitlin Olson’s DJ, Deborah Vance’s headstrong yet lovable daughter.

While it’s hard to say goodbye to any character, bidding farewell to “Hacks” was especially “bittersweet” for Olson, who notes, “It’s hard to find a show that has such a beautiful, seamless blend of comedy and true emotion and connection, relationships.”

“This is a really special show, and it’s also just a really incredible cast and crew,” Olson told TheWrap. “A lot of these people, it was their first television job, and so [we’ve] kind of grown up together … It’s just been such a special thing to be a part of. I’m so honored that they wanted me to do it.”

Olson also applauded creator trio Lucia Aniello, Paul W. Downs and Jen Statsky for making the choice to end “Hacks” on a high and go out on their own terms.

“I’m so proud of them for being able to end their series in their own way — not very many people get to do that,” Olson said. “While it’s sad, I think it’s the right move.”

While Olson’s DJ does get her own emotional goodbye (more on that below), the “Hacks” creators filled DJ’s sendoff with plenty of laughter in a crossover episode with “The Amazing Race” that was in the works for years.

With “The Amazing Race” on DJ’s bucket list, Season 5, Episode 5 sees DJ beg Deborah (Jean Smart) to partner with her in the reality competition show’s fictional celebrity season. Deborah eventually gives in thinking it’d be good promo for her Madison Square Garden show. The mother-daughter duo soon find themselves competing alongside Property Brothers Jonathan and Drew Scott as well as “I Love LA” star Jordan Firstman and social media personality Trisha Paytas, with Phil Keoghan also making an appearance. 

As a fan of “The Amazing Race,” herself, Olson relished the opportunity and embraced the physical comedy aspect of competing on the CBS reality series.

“I love doing anything physical — I love screaming and yelling at people,” Olson said. “The idea of having DJ do this with Deborah … I mean, it’s just a perfect combination of thrusting two people together who neither one of them are very good at it. What a gift. I read it, and was incredibly excited. It was so much fun to shoot.”

For the shooting of Episode 5, Olson and Smart were quite immersed in the world of “The Amazing Race,” with the same camera crews from the series running with the duo and the producers and Keoghan available for any questions they might have.

“Everyone wanted to make that very authentic, so there were certain things that we were and were not allowed to do,” Olson said. “We were also out in the middle of nowhere. It was like 95 degrees. It was … appropriately miserable at times and just so much fun.”

Of course, shooting those final scenes alongside Smart was a treat for Olson. “We do something together and we cut and she’s just laughing so hard — she’s very effusive with her joy for you and her compliments, and it just makes such a warm environment … I don’t care about anyone else — I just want to make Jean laugh.”

After over five years of playing mother and daughter on the show, Olson and Smart didn’t even have a conversation about how their dynamic would be in this ridiculous premise, with Olson noting Deborah is “very clearly” there for her career while DJ is “letting herself believe that her mom’s doing it for her.”

“She also knows that her mom doesn’t believe that she can do it, just like she has with anything else in her life, and she’s just really trying to prove it to her,” Olson said. “DJ is sort of forcing this bonding moment, but I think that it’s the same dynamic that you’ve seen over the series … We kind of settled right into that.”

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Kaitlin Olson and Jean Smart in “Hacks” Season 5 (HBO Max)

The “Amazing Race” crossover put Olson in some unusual situations, including milking a goat — which Olson said she learned to do on the day, though the goat “wanted nothing to do with me — but I got her” — to a cheese-wheel stunt to a clown dance, at which DJ fails miserably despite insisting they should do it.

To say the least, DJ isn’t in her element during the clown dance, which Deborah has no problem with. To prepare, Olson did just the opposite.

“They kept sending me the choreography, and then sending me the music, and I was like, ‘I’m not supposed to know how to do this, right?’ So I really didn’t look at it at all until the day. I was excited to just go up there and do dumb things with my body,” she said.

As DJ’s failure with the dance wraps up their time on “The Amazing Race,” shooting the clown dance also wrapped Olson’s time on “Hacks.”

“Everyone came to the stage, and not just the cast, but all of our crew that we’ve worked with for five, six, seven years,” Olson recalled. “It’s truly a very special family. I’ve worked on a lot of shows, and not every crew and cast get along as well as these guys do … I’m so grateful that people love the show, but I also just have to vouch for the fact that it’s very special behind the scenes as well.”

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Kaitlin Olson and Jean Smart in “Hacks” Season 5 (HBO Max)

Despite their loss, the subsequent Episode 5 scenes give some closure to DJ’s character, with Deborah applauding her daughter’s resilience and desire to stretch herself into new endeavors, leading up to DJ finally achieving her dream by selling her detachable jewelry on QVC.

The appearance on QVC marks a “full circle” moment for DJ, Olson said, noting the opportunity is symbolic of the trust Deborah finally has for, and offers some redemption to her at-times juvenile character.

“This person isn’t a perfect person — she’s ridiculous and she’s a big baby, but she tries really hard,” Olson said. “I think that her mom’s belief in her is something that she’s been looking for since she was a child, so to finally get it, it’s just a nice way to wrap it up and have her … go off and do whatever she’s going to do — hopefully, a lot more different D’Jewelry.”

DJ’s arc and growth was especially rewarding for the actress, who pointed to her realization after Season 3’s roast that she doesn’t need Deborah’s approval, and that, in fact, her mother was as broken as she was.

“DJ always thought that she was the one who was broken, and after that, she sort of realizes Deborah’s an addict, and she’s addicted to making people laugh, and it maybe isn’t her not being good enough,” Olson said. “I like that she slips back into it, because, just because you realize that doesn’t mean that everything’s fine from now on, but sort of getting to a place where then she becomes a mother, and she gets to set some boundaries.”

That said, Olson admitted she’ll miss the “adult temper tantrums” DJ throws, though she’ll find a way to incorporate that element somewhere in her lineup of projects, which include ABC’s “High Potential” and FXX’s “Always Sunny.”

“I’m so fortunate to be able to bounce back and forth and play different characters,” she said. “I do feel like the luckiest person in the world.”

While “Hacks” is closing its doors, Olson likes to assume it won’t be the last time she works with the cast and crew, particularly applauding star Hannah Einbinder’s “natural, raw talent.”

“She’s got a long career ahead of her, and I would love to work with all of them again,” she said.

“I’m hugging my castmates, who, this is their first show, and I can see that they feel like this is the end, but …. they’re very young people — they have big, long careers ahead of them, and they’re very talented, so I hope that they know that,” Olson said.

“Hacks” drops new episodes Thursdays on HBO Max.

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