Kaitlin Olson Won’t Stop Going There

The 'Always Sunny' star tells Playboy how the show is tackling the reproductive-rights debate, and how she keeps taking risks

Television November 21, 2019


It’s no small feat that It’s Always Sunny in Philadelphia has expertly managed to stay clever and relevant, even 14 seasons deep into the iconic “gang’s” misadventures. And it isn’t doing so by suddenly playing it safe. One of the episodes that aired Wednesday night on FXX, titled “A Woman’s Right to Chop,” is a stunning satire about abortion (!) wherein the guys of the group—Mac (Rob McElhenney), Charlie (Charlie Day), Dennis (Glenn Howerton) and Frank (Danny DeVito)—go on the offensive to stop women from cutting their hair at the new salon that opens up next to their watering hole, Paddy’s.

The guys’ aggressive disgust with the women’s haircuts—from all but Charlie, who thinks the haircuts are just hideous hats—perfectly sets up Dee’s line, “If women want to get short, ugly, lesbian haircuts, then they deserve to do that because it’s their body and therefore their choice.” It’s a succinct ethos for this and most of their episodes: Sometimes the truth has an imperfect messenger.

If you’re offended, you probably have missed the point and need to watch it again.

Imperfect is a generous description of Sweet Dee, or any of the characters, but it is exactly these human-like flaws that allow the show to go there without feeling self-righteous or congratulatory. After all, if these unjustifiably arrogant characters can get the point, there’s hope for everyone. Ahead of the season 14 finale that aired this week, PLAYBOY spoke with Kaitlin Olson—who has crafted Dee into the elite ranks of hilariously flawed women in TV history—about the state of comedy (re: this never-ending woke-culture debate) and how Sunny keeps pulling off nuanced commentary on high-stakes issues, season after season.

“One of the reasons I’m most proud to be on this particular show is because our writers are so smart and funny, and it’s such a rare combination,” Olson explains. “I really feel very safe in knowing that, look, you can watch an episode, and if you’re offended, you probably have missed the point and need to watch it again.”

The second story line in this episode (introduced in the same cold open) proves her point. Mac’s dog, Poppins, who’s been absent for several years and must be at least 40 years old, returns to the bar as a patron opens the door, interrupting their hair debate. The guys rally around comically absent Poppins’ right to leave and hunt and gather and be free because Poppins is a male dog. When Mac and Charlie take Poppins to the vet, they have to confront two hard truths: The dog they thought was male has been female all along, and she’s pregnant. The veterinarian explains that if this ancient dog has puppies, she will die during birth. Without missing a beat, Mac says, “Well, then, you gotta kill those babies.” When pressed by Charlie on how he was pro-life literally the scene prior, Mac follows with, “Oh, this is different because it affects me.”

The line is as uproarious as it is gratifying. Many people on the pro-choice side of the abortion debate have argued that until you find yourself in the position of a person considering abortion, you should reserve judgment on that deeply personal decision. The moment that Mac must make this decision as Poppins’ proxy, he chooses without hesitation to save the dog’s life. In a time when abortion access in many states is limited, and Roe v. Wade is likely to return to the Supreme Court, there’s no better time to elevate the issue. Still, the episode is likely to ruffle some feathers.

Kaitlin-Olson embed01
Courtesy Byron Cohen/FXX.

Olson tells me that it’s not in her nature to want to offend anyone, but also that after 14 years, fans have come to expect a strong point of view and creative ways into exploring almost any topic. “There’s always going to be people who are like, ‘How could you do this? This is horrible,’” she says. “I don’t know that it’s horrible. I think we’re making a comment on ludicrous behavior on both sides of an issue. So we’re commenting on extreme behavior everywhere.”

Still, Olson acknowledges that some new viewers can miss the joke or become incensed when they don’t realize that many of the show’s jokes are callbacks to things the gang covered more deeply in prior seasons.

“We got a lot of comments on the episode ‘Dee Day,’ where Dee makes the guys dress up as her ridiculous sketch-comedy characters. And that’s a callback to episodes from years ago, where Dee is doing characters that she thinks are hilarious, and the rest of the guys point out that they are not hilarious. They’re horrifically racist. We’ve already explored it, so when we call back to these characters, a lot of people got really offended by that. We’ve already addressed the fact that this is not funny. It’s racism. Dee doesn’t get that ’cause she’s an idiot.”

In comedy, you have to be willing to stand by what you say. So when some male writers, directors and comedians complain that so-called “PC culture” is ruining the genre—even as, ahem, one of those complainers’ gritty origin film has recently made a billion dollars worldwide—Olson is quick to point out how the rules really haven’t changed, and that you should expect as much backlash as you do praise for your point of view.

I definitely am your go-to if you’re looking for a loud, angry woman. It’s so absolutely not me.

“If it’s making you cringe as it’s coming out of your mouth, maybe it’s not the right way to go about it,” she offers before reflecting on her own show. “I feel like if what we’re doing is offensive or upsetting or it’s disrespectful, then maybe we’re not doing our job. Maybe we need to be a little bit smarter about how we’re approaching the subject. You just gotta stand behind it if you’re going to do it, and you gotta be prepared for the backlash.”


Kaitlin Olson is a good actress. Beyond the longevity of the show, I know this because it only took a few minutes speaking with her on the phone to confirm that she is nothing like her character, Dee Reynolds. She was warm and open to me, aka a stranger calling from an unknown number at 10 a.m. to talk at length about an incredibly heavy topic. Her talent for playing total assholes is in stark contrast to the happy family life Olson personally enjoys with husband and costar McElhenney and their two children.

“I have a spoiler: This will never happen for Dee,” she promises. “I don’t know where the show’s going, exactly. But I can tell you that Dee will not end up happily married in a loving, calm family.”

Olson is most widely known for playing Dee, and we spoke about how, after she booked the role, it was revealed that the dialogue she’d performed was actually for a different character, and Dee was much flatter and less outrageous. Because of this, the first few episodes of the series are Olson’s least favorite, but it wasn’t long before the writers—including Day, Howerton and McElhenney, who are all executive producers—picked up on her comedy chops and timing and started writing more for her.

We’re making a comment on ludicrous behavior on both sides of an issue.

“[McElhenney] guaranteed me that they actually did want Dee to be not only funny, but just as narcissistic and deplorable, really, as the rest of them, which is way more fun to play,” she says. “To their credit, they very much paid attention to the things that I was doing that made them laugh, and they wrote to that, and we sort of created this character together, and I’m really proud of it.”

When I list several other characters she’s played—Helen from Bob’s Burgers and Mickey from The Mick came to mind—she laughed. “I definitely am your go-to if you’re looking for a loud, angry woman. It’s so absolutely not me. I grew up very, very insecure and shy. There’s something so funny about an incredibly loud, insecure person.”

And while Olson sometimes feels typecast, she excitedly tells me about a new show she’s working on with Will Forte for Quibi, the Jeffrey Katzenberg app project that features short-form content from all of Hollywood’s big names, launching in April. She assures me that this project will see her playing a “very different character” than Dee.

Fourteen seasons, unending absurdity. When Kaitlin Olson looks back on the past 14 years, she seems at her happiest. In that time, she met her husband, had children and built the foundation of a career that shows no signs of slowing down. When I ask her if she ever dreamed the show would mean this much and be such a success, she admits she hadn’t.

“We just wanted to make the show that we were proud of, and we got to do it, and we were happy. So the fact that as an added bonus, now people are watching it, and we’ve been able to make a living off of it and do it for so long—that’s just really like the icing on the cake. But the thing that I’m most proud of is that we were just as happy 12, 13 years ago.”

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