Kaitlin Olson Has Some Damn Good Advice For Parents of Boys

"Your kids are always watching."

by Donna Freydkin
Originally Published: 
GETTY / 20th Television / Disney

If Deandra “Sweet Dee” Reynolds ever had a child, she’d be a lot like DJ, the petty, needy, pill-smuggling, deeply insecure celebutot Kaitlin Olson plays on HBO’s Hacks. The new show is an ode to bad parenting, and entitlement, far sharper and funnier than you’d have reason to expect. And it’s the perfect companion piece to Olson’s portrayal of the “Aluminum Monster” on the bitingly hilarious modern classic It’s Always Sunny in Philadelphia. Playing a third-rate grifter on that show, Olson has mastered the deft art of being both loathsomely conniving and defiantly pitiful, a former high school laughingstock whose own mother called her a mistake in her will.

The real Olson is none of the above, in case you were wondering. She’s nice to a fault. “That’s always really funny to me, people who are not self-aware and who are entitled and demanding. I think it’s just the opposite of who I am. I’m way too aware of how people are perceiving me or what I’m doing. So it’s funny to me when people just have zero awareness and feel like they deserve absolutely everything,” says Olson.

A week or so prior to this interview, she had dodged traffic on a Los Angeles freeway to rescue a lost dog. Olson took him to the vet, his injured legs were bandaged, and Olson’s husband Rob McElhenney documented the saga on social media. In one of the isolated instances of it actually being a force for good, the posts reunited the runaway canine with his distraught family. Now, with her heroics behind her, Olson talks to Fatherly about what’s next for Sweet Dee, her love for Brad Pitt, and how she and McElhenney survived 18 months of lockdown together.

I have been breathlessly following your dog saga. You saved Brad Pitt!!!!

He was so handsome. And so I took him to my vet and they were like, ‘We just need a name.’ So I wrote Brad Pitt because he was so handsome. And then they’d call and say, ‘Just wanting to let you know Brad Pitt’s doing really well.’ First of all, my heart is broken. I fell in love with the dog. I’ve been keeping in touch with the family. His paws are healing up. He’s home and he’s happy. And now I think I might need to open up some sort of animal rescue.

It wasn’t just me. There was a little team of us that were clearly trying to slow everything down and get up on the side of the dog and veer it off to the side. And there were people that would be coming up behind us, and honking and trying to zoom behind us. It was so scary.

Awww, and here you are, playing the exact opposite on Hacks. I don’t think your character would get her mother a glass of water, much less help her chase down a scared dog.

It’s a complicated relationship. They’re all they have. They love each other and need each other, but also, it wasn’t the greatest parenting. My character is going to pout about it for the rest of her life. And yet at the end of the day, all she wants is for her mom to love her. The fact that she’ll go to her grave feeling like her mother still owes her.

And Jean Smart, who plays your mother, is absolutely staggering on the show as a nearly washed-up but indefatigable comedian.

I always knew that she was a goddess in human form. I didn’t realize how welcoming and selfless and lovely she was. She’s a genius and she’s also a lovely person.

You shot during the pandemic. Was it nice to get back to work, part-time?

It was a lovely break and it was actually perfect for me because I don’t think I was prepared to go back full time. But leaving my house for a few days at a time working and then coming home for a few days and then going for a day — that was kind of perfect. I needed to tip toe into it.

How did you and your husband hold up, with all the togetherness?

I’m just very proud of everyone. And Rob and I have zero right to complain because we live in an area where — I’m currently in our guesthouse office area. We have a yard. We have different places where we could be like, okay, we’re all sick of each other here, kids go outside. I would have to go take little breaks and breathe deeply and then come back out. Remote school was really hard and challenging. My kids were in second and third grade when this started and they had no idea about technology at all. I had to learn Zoom and we had to figure out Google Docs and Seesaw and all the programs. I’m in the dining room, running from one end of the table to the other, trying to help both of them.

What can you say about the new season of It’s Always Sunny without anyone firing you?

We’re going to start shooting season 15 in the summer. I can say whatever I want. They can’t fire me. I married the boss. They haven’t even started in the writer’s room. So there’s nothing even to give away. Since we are mostly a satire, I think there’s going to be plenty of material. I feel absolutely like the most fortunate person in the world for so many reasons, not even just the longevity of the show, but the quality of the show. It’s truly a show that if I wasn’t on it, I would love it and watch it.

And I also met my husband and we have two kids now and this beautiful home. I will forever be grateful for this show. It’s just changed my life. And it just keeps going. I don’t feel like it’s stale yet either.

How did you figure out your rhythm in your relationship, given that you’re both costars, married in real life, and the parents of two boys?

The answer to this question before COVID was that it was amazing because we never really see each other because he’s always working or I’m off doing something else or I’ve got the kids. We have little moments of the day where we see each other and then when we’re working together, it’s great because we get to spend the day together.

But now we’ve spent 18 straight months together. It’s a little bit of a different answer. I think that Rob is one of the smartest, most talented people I’ve ever met and I’m in awe watching him work. He thinks I’m funny and we love working together and we just have a really good time. I met him on the show and our first couple of years, that was our experience working together.

You’ve got two boys, Axel, 10, and Leo, 9. I spoke to your husband last summer, and we talked a lot about the notion of toxic masculinity and how to model behavior in front of your children. How do you approach that with your son, for example?

He’s got two parents that model it constantly and we’re not doing it on purpose. I just have two great kids. We talk a lot about consent and respect and leaving a place better than you found it. They’re at the point now where they’re like, ‘We get it, mom.’ I don’t know that it’s much more than making sure that you live your life in a way that you’re proud of, because your kids are always watching. They’re polite and respectful.

If they’re ever in the middle of like screen time or whatever, if somebody is coming into or leaving the house, we have a housekeeper, we have a nanny — they have to put down their things and make eye contact and say hello and goodbye. And we talk about why and the impact that you have on someone. You never know how that’s going to affect them if you ignore them. And then my third boy, Rob, I have to be like, ‘Hey, can you put your screen down and say hello to your kids?’

Hacks streams on HBO Max, starting Thursday, May 13.

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