Kaitlin Olson And The Perils Of Being A (Funny) Woman In Hollywood

As Season 10 of It’s Always Sunny gears up, Olson looks ahead to what a life after Sweet Dee would be like. Sometimes I’m like, Oh well, they just wanted a young pretty person, rather than a funny person.”

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.”

“She’ll pick something from the garden to heal a wound and it will magically disappear,” her friend and fellow actor Tricia O’Kelley (of Gilmore Girls and Devious Maids) says. Day: “In the 10 years that we’ve been doing [the show], I don’t think I’ve ever seen her get a cold. That’s quite an accomplishment.”

Her weakness is watching any of the Real Housewives shows, and she says that if she ever does get time to relax, she’ll check into a hotel nearby to “literally just order room service with a girlfriend and get massages and drink wine and watch Bravo.”

And because her private life is so starkly different from her television persona, she tends to keep it under wraps. “I feel like people only want to hear me say funny things. Like, I don’t tweet about my kids or being a mom ever, because I’m very aware that that’s annoying for people to hear,” Olson says. “So everything is true, but I just feel like my motherhood life is sort of private, because it’s so special to me I don’t want it attacked or to have that part be annoying to people.”

And everyone around Olson mentions how her role as a mother is an enormous part of her identity. “Motherhood has changed her a lot for sure, it’s by far her number one priority is those children,” O’Kelley says. “Everything else comes in a distant second. Her family as a whole — Rob, their marriage — her family is her priority.”

When asked what he sees as being next for Olson, her husband agrees that while her career is a priority, family will always come first for them. “She would love to build out a movie career and see what’s next in television,” McElhenney says. “But I do know the thing that’s most important to her now is to make sure these boys are raised well.”

Olson concurs. “Parenthood has become number one,” she says. “So I’ll only take something if it fits in, and if it doesn’t interfere with my ability to be a good mom. And that’s the truth and that’s how it will always be, because I feel that.”

Photograph by Macey Foronda for BuzzFeed

Motherhood might be Olson’s priority at this point, but acting is a very real and large part of her world. “I would love to do more film,” she says at one point. “I really like TV, but yeah, in the interests of doing something different I would love to do more films.” She pulls at her silk shirt. “I’m not having any more babies. I want to work.”

In a year when Time named 2014 the “Best Year for Women Since the Dawn of Time,” it’s still a year where female-led comedy shows like Selfie, Super Fun Night, and Trophy Wife were canceled. And a year in which the most anticipated female-driven comedies — Tammy, Obvious Child, and They Came Together — made a very small dent in the film landscape. Obvious Child grossed just $3.1 million at the box office, and They Came Together grossed under $1 million. While Tammy was a financial success, making close to $100 million at the box office, if you compare that to male-driven buddy comedies like 22 Jump Street (which grossed close to $200 million), there seems to be a disconnect between what Hollywood is offering and what Americans are seeing.

“Look, I’m never going to understand what Middle America wants, because I’m on a show that Middle America doesn’t necessarily like, but I think is really funny,” Olson says, wrapping her arms across her chest. “I think there’s definitely a shift, and no one’s funnier than Melissa McCarthy and she’s doing really well, you know, so hopefully.”

Sasha Roiz and Olson on It’s Always Sunny in Philadelphia FX

Whether or not middle America likes Sunny or Olson, there does seem to be a shift happening. Ellen DeGeneres hosting the 2014 Oscars led to an 8% increase in viewership, and Tina Fey and Amy Poehler have hosted the Golden Globes for the past three years, but is that enough? “For sure, there’s not enough funny roles for women in Hollywood, period,” Howerton says. “I’m happy to say that we personally — in Sunny and other things that we’re working on and have written — always try to make it a priority to write funny female roles.”

Even if what Olson and Howerton say is true — that Middle America doesn’t like the kind of comedy Olson wants to do, and there aren’t enough comedic roles for women in general — what does that mean for Olson as she leaves Sunny to explore other roles? Where do you go when the film and television landscape isn’t in your favor?

Olson doesn’t seem entirely sure, other than that she’d like to try out a character who isn’t quite so heightened and extreme as Dee. “I don’t know that I want to do something super dramatic. Our show and our characters are so heightened; I would like to do a more realistic person, who’s going through something really hard, but deals with it in a humorous way,” she says. But at the moment, those aren’t the parts she’s being offered.

“What I get a lot of is ‘We know you can make this funny.’ Stuff that’s like, it’s OK, but then I’m supposed to make it funny,” Olson says. “It’s a great compliment… But I don’t know if I’m interested in taking something that’s OK and being the one that’s responsible for making it funny.”

“I think a lot of men are scared to act opposite a woman who is as funny as they are.”

When asked why she thinks she hasn’t been offered more roles at this point, Olson says, “Sometimes I’m like, oh well, they just wanted a young pretty person, rather than a funny person. That’s discouraging, because there’s nothing I can do about that.” Olson pauses, and then softens the blow with, “I love my job. I got really lucky. I love my character and this circumstance, but it is a little confusing why, in my off time, I’m not doing more. I can’t really blame it on ‘oh well, I’m pregnant’ anymore.”

The actors who have worked with Olson know what she’s capable of, and vehemently speak of her potential. “I’m pissed off at the world that she’s not a giant movie star,” Ellis says of Olson. “I just think she has so much to offer: She’s a great comedian but she’s also a great actress.”

For his part Howerton offered his own take. “I just think it’s a shame that she hasn’t been more recognized, and that more roles have not been thrown at her. I think a lot of men are scared to act opposite a woman who is as funny as they are, and who will give them a run for their money for being the funniest person in that project,” he says. “And I think a lot of times she doesn’t get cast in things because she’s so funny, and I think that’s fucked up.”

When asked if this was at all true, Olson appears hesitant to answer and seems borderline uncomfortable. She pauses before responding. “I hope not, but I feel like that’s happened a few times. I just hope that, if it is true, it starts to shift soon. Because it’s a shame. I don’t know if I can answer that question. I don’t want you to print anything I have to say.”

After a long pause — where she leans across the table, then sits back and re-tucks her legs into her chest — she says, “Yeah, I just, I love Glenn for saying that and for recognizing it, and, well, you know, Rob says all the time, he’s like, ‘Look. That must not be what America wants because if it were, you’d see more of it.’ People, women, want to see women being pleasant. But for some reason, we want to see men be really funny. I think that’s starting to change, you know, ever since Bridesmaids really. So that’s really awesome. I think that’s the part that I’ll focus on and just hang in there.”

During a time where Olson does have to consider and weigh every word she says, because those words could lead to her next big role or prevent her from landing it, it’s clear that she’s nervous about it all — about posing with the tree, how she’ll be perceived by viewers, and what people think of her, and wanting to be liked by an audience larger than the one she’s cultivated with Sunny. “I hope it’s not threatening for me to be as funny as I can be and work with a really funny man,” she says emphatically, straightening her posture and finally relaxing. “To me, that sounds like an amazing movie.”





















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