Kaitlin Olson is hating having her picture taken right now. The 39-year-old star of It’s Always Sunny in Philadelphia doesn’t say this out loud, but it’s not hard to tell that she is deeply, deeply uncomfortable — though she’s nowhere near as awkward in her own skin as her character Sweet Dee, a caustic and narcissistic would-be thespian, on the FX (and now FXX) cult comedy. “Could you play a bit with the tree?” the photographer gently asks her.
It’s an unusually warm Friday afternoon, and Olson is standing in the backyard of her contemporary Sherman Oaks home. The lawn is sprawling, with a trampoline on one end and a pool at the other; toy cars and pint-sized seats, the cast-offs of her two young children, litter one corner. A stylist fixes Olson’s hair as she begrudgingly twists her fingers through the tree’s branches. “Just hanging out, touching my tree,” Olson says out loud, to no one in particular. “You like photo shoots? It’s pretty great, standing by yourself, taking photos.”
For a seasoned actor like Olson — who’s been working consistently for the past 15 years in comedy roles, turning up on Curb Your Enthusiasm as Becky, Cheryl’s loud and opinionated sister; as Mimi’s vengeful nemesis, Traylor, on The Drew Carey Show; and currently on New Girl as the free-spirited girlfriend of Jess’ dad — it’s surprising that she’s not used to the being the center of attention by now. But she’s decidedly not.
The truth is, though, that Olson feeling anxious about this interview and photo shoot is entirely understandable. She’s heading into a 10th season of Sunny, and while that’s a place any actor would envy being in, she’s also arriving at a crossroads in her career. As Sunny begins to wind down, Olson will soon be leaving a show on which she’s been a linchpin for 10 years, and will have to look around the corner to see what lies ahead for her career.
“Could you maybe relax your shoulders a bit more?” the photographer asks her, trying a different tack. “I don’t know,” Olson says, laughing at the word relaxed, “because I’m definitely not.”
Photograph by Macey Foronda for BuzzFeed
The biggest role in Olson’s career to date remains the 10 years she’s spent on Sunny as Deandra "Sweet Dee" Reynolds, a horrifying example of a human whose self-centered streak is often a driving force in the storyline. Such as in the Season 8 episode “The Gang Gets Analyzed,” when Dee’s therapist calls her out for lying about being the first choice as the female lead in The Notebook, and the episode ends with Dee repeating, “Tell me I’m good,” until her therapist finally relents. Or in a third season installment, “Dennis and Dee’s Mom Is Dead,” when Dee hears from a lawyer that she won’t be getting any inheritance, because she was "a mistake" (despite being Dennis’ twin), and her knee-jerk reaction is to dig up the grave so she can steal the jewelry off her mother’s dead body. But rather than be repulsed by her character’s more detestable nature, Olson has been able to connect with Dee.
“I can't tell if I relate to her anymore or if I'm just so used to playing her and love her so much that it's second nature,” Olson says. With the photographer and stylists gone, Olson finally seems more at ease, sitting at a long wooden outdoor table in her backyard and tucking her legs into her chest. “There's a certain element of desperation and wanting people to like you… I was really shy. But I think because that was so sad for me when I was little, that it's so hilarious and sad now, that I relate to that. I like this character's way of handling it, way more than how I handled it. Which is, like, aggressively and angrily. Maybe it's cathartic. I don't know.”
“I was really proud to make Larry [David] laugh. The more I would yell at him the more he would laugh.”
And Olson not only relates to the idea of needing to fit in, but it’s something that’s apparent just from talking to Olson. Often she’ll end sentences with “I don’t know,” like she’s trying to take back what she just said in case you don’t like it. Several times, she stops herself from answering a question with “I don't know if I can answer that question. I don't want you to print anything I have to say,” or “I don't know how to answer that, again, without having it in print sound like I'm being a real arrogant asshole.” Refusing to answer tough questions about Hollywood and her role in it proves doubly problematic though, and she softens the blow by pointing at the recorder and saying, “I'll tell you when your thing's off.”
That need to be liked started long before Olson made it to Hollywood, and it’s what initially led her to start performing. Olson grew up in perhaps the most un-Hollywood setting — on a six-acre farm in Oregon. Olson says her mom would whistle when it was time for dinner, and if you wanted a snack, you just ate out of the garden.
“Nobody was an actor,” Olson says of her family. “I started doing summer camp stuff in elementary school and loved doing the plays. I liked making people laugh. I remember that specifically, being really young and having my parents being in the audience and laughing. It wasn't really a Oh, I'm the center of attention feeling, it was more Oh, I'm making them so happy right now feeling. I liked that.”
Olson — with Julie Payne, Cheryl Hines, and Paul Dooley — rails at Larry (Larry David) on Curb Your Enthusiasm
HBO
That sense of accomplishment — of making someone happy — is what drove her to attend the University of Oregon and major in acting, and it’s what would eventually take her to Los Angeles to fully commit to her vocation. “I thought it was beautiful. It was so sunny. It's so cloudy and gray and rainy in Oregon,” Olson says of moving to Los Angeles. “I didn't understand how anyone could ever be sad or depressed here. It was so beautiful.”
She took classes at The Groundlings and eventually made it into the Sunday company. To support herself, Olson worked three jobs: as a recruiter for a biotech company; as a receptionist in a hair salon; and as a salesperson at a boutique shop. “I worked hard,” Olson says. That determination paid off when she landed an audition for Larry David’s HBO comedy Curb Your Enthusiasm. “I'm not the ballsiest person, so I was very proud of myself for getting it,” Olson says. “I was really proud to make Larry laugh. The more I would yell at him the more he would laugh. Which was really fantastic. I loved that.”
Patrick McElhenney/©FXX / courtesy Everett Collection
It’s Always Sunny in Philadelphia originally started as a “writing exercise,” according to Rob McElhenney, who made a $200 homemade video pilot with Charlie Day and Glenn Howerton in an apartment. That pilot then sold to FX in 2005, and was given a budget of $400,000, less than a third of the cost of a traditional network comedy. It was shot with the caveat that they’d need to reframe the original storyline from being centered on three actors in Los Angeles to a group of friends who tend bar in Philly.
According to Howerton, one of the show’s executive producers, who also plays Sweet Dee’s twin brother, Dennis Reynolds, on the show, Olson came up against some stiff competition for the role of the hilariously vulnerable Dee; the final two actors considered were Olson and Kristen Wiig, according to Howerton, but in the end Olson landed it. (Wiig’s publicist did not respond to multiple requests for comment.)
“I knew her work from seeing her in Curb,” Howerton tells BuzzFeed News. “We wanted to find somebody who could be as funny as the guys, and we felt a lot of times in comedies, girls are so often relegated to the ‘oh, you guys’ role.”
Day, who fans know best as the ever-screaming and always emotionally unstable Charlie Kelly, echoes the sentiment that casting Olson was a no-brainer.
“We were blown away by how funny she was,” says Day. “I can’t think of an overall impression other than our general excitement that we found someone who was really right for this part.”
Oddly enough, it was McElhenney — to whom Olson is now married — who was less than convinced about her. During the audition, Olson accidentally left out a critical line in the script they’d given her, and McElhenney was nonplussed, to say the least.
Howerton and Olson in an episode of It's Always Sunny in Philadelphia
FX
“I left the room and Rob was like, How did she leave out the funniest line that was in there? and he didn't want to cast me,” Olson says. “Rob, who I've now married, had to be talked into hiring me.”
The first time Olson and McElhenney met was during her audition, and despite any apprehension he had, she was cast as Dee, and the show premiered in 2005. Somewhere during filming Season 2, the pair started dating, though they wouldn’t officially come out as a couple until the show’s third season.
“Literally, the stupidest thing you can do in the entertainment industry is start dating your co-star on a television series that’s expected to continue,” McElhenney says in a phone interview. “Potentially, we could’ve ruined the dynamic of the TV series, but we jumped in anyway. I guess because I started to fall in love with her.” His voice softens as he says it.
They married in 2008 and have two sons, Axel (age four) and Leo (age two).
Mary Elizabeth Ellis, who plays The Waitress on Sunny and is married to Charlie Day in real life, first met Olson when they were on a flight to shoot the pilot. “The guys flew to Philly early, and I flew on a flight with Kaitlin,” Ellis explains. “We had a lot of cocktails together and were like, OK, you’re great, we’re going to be best friends.”
Ellis vividly remembers the moment when she found out Olson and McElhenney were dating. It was during a press junket, and they all sat down in a hotel room. “They were like, ‘We have something to tell you guys,’ and Kaitlin just starts crying and says, ‘I love him. I love him so much, you guys. He’s such a great person. We don’t want you guys to be mad at us because we’re dating and on the show,’” Ellis says, laughing. “It just made us laugh so hard, because it was such a funny way to reveal that they were dating for the first time. They’re just so great together.”
Patrick McElhenney/FX
None of this would have happened if Olson had chosen not to take the role of Sweet Dee, which she considered in those early days.
The character was written as the typical straight man, which Olson had no interest in playing. “There were three episodes that were already written that I had to do that were just very like, ‘You guys. Come on, you guys. That's stupid, you guys,’” Olson says. “But I was very clear about not wanting to do that.” (“I don’t think we did a great job writing her character the first season,” Howerton says.)
It speaks to Olson’s character that she wasn’t willing to just simply lay down and read the lines she was dealt; she took an active role in shaping the character and how she wanted to play Dee. “She pulled Rob aside, because he was the showrunner, and said she didn’t want to do the show if her character wasn’t funny,” Howerton says.
Olson only took the role after many conversations with McElhenney about how the character of Dee would be shaped. “He was like, ‘Look, we just don't know how to write for a woman, but we'll figure it out,’" Olson says. “And I was like, ‘Well then, don't write for a woman. Just write — look at all these great funny characters you wrote. Just write one of those. I'll make it female.’"
Despite initial character setbacks, the Dee of the past nine seasons is hilarious, and the most physically comedic role on the show. (Witness her free-form dance moves.) Dee’s actions don’t fall victim to the conventions usually dealt to women in comedy. Dee was Bridesmaids before there even was a Bridesmaids. She is crude beyond belief at times. She flails her arms and spits venomous, half-baked threats at anyone within earshot. She falls — a lot — and fake-vomits so convincingly that it’s become a running gag on the show. “I’ve never heard somebody do a gag so funny,” Howerton says. “You know, suppressing puke, it’s just a weird gift she has.”
Olson runs head-first into a parked car on It's Always Sunny in Philadelphia
FX
In the second season episode “Charlie Gets Crippled,” Olson wears a back brace and hobbles on crutches as she drags her legs behind her. In “Who Pooped The Bed?” she runs out of a shoe store in stilettos and slams headfirst into a car so hard that there’s a dent, a stunt Olson performed without a stunt double.
“We had a stuntwoman do it, and it didn’t look very real, and then Kaitlin did it, and actually ran into the car, probably almost breaking her neck,” Day says with a laugh. “It’s just one of the funniest moments of physical comedy I think in the history of the show.”
Olson furrows her brows as she stares across the lawn. “I don't want the stunt double to do it, unless it's like a quick thing, because that's part of the acting. I want to do that,” she says. “There's a lot of acting that happens in between the running out and the head-hitting.”
The only problem is that Olson is extremely clumsy. “If there is a tack on the floor, she will step on it,” Howerton says. During the filming of Sunny, Olson has broken her back, her foot, her heel, and while on set, she fell through a floorboard and ripped her calf open on a metal spike.
“Our idea of Dee was not as physical as Kaitlin is,” McElhenney says. “It’s something we sort of found with the way she carries herself.”
Olson sighs. “I'm very long,” she says. “I'm very unaware of how long my limbs are and I bash into things a lot, and Rob makes fun of me a lot… I'll do something and Rob will tell me to do it again and I didn't even know it was funny.”
Photograph by Macey Foronda for BuzzFeed
Olson is, as Howerton says, nothing like her Sweet Dee character, though fans of the show often have a hard time accepting that. “They assume I'm drunk and loud and that I want to do shots and stay up all night,” she says, laughing.
The home that Olson shares with McElhenney is immaculate, despite the fact that they have two children under the age of four. When her youngest, Leo, comes home from school, her entire face lights up and she wraps him in a warm hug before excusing herself to put him down for a nap. And an ideal Friday evening is one spent at home, according to both Olson and McElhenney. “A perfect night is coming home, having dinner, putting the kids to bed, and opening a bottle of wine and watching Game of Thrones,” McElhenney says.
Olson is often described by those who know her as nurturing and protective — “I think of her as a lioness,” McElhenney says. “She’s extremely protective of her children, like I fear oftentimes for my life if I cross a line. I’m afraid she’s going to snap my fucking neck. The way a female lion might with her cubs.” — very un-Dee qualities. She was “raised by hippies” in Oregon (McElhenney’s words) and cooks organic food, grows herbs in her garden, and uses homeopathic remedies.
"My motherhood life is sort of private ... it's so special to me I don't want it attacked or to have that part be annoying to people.”
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