'It's Always Sunny in Philadelphia': Kaitlin Olson Struggled to Find 'a Female ***hole' to Play

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Kaitlin Olson has played Dee on the FX comedy It’s Always Sunny in Philadelphia for 15 seasons over 17 years. When the show first started, Olson considered the role of Dee a revelation. There are more roles like Dee now, but Olson had wanted to play “a female ***hole” for a long time before 2005.
Olson was a guest on the Basic! podcast on Oct. 19. She looked back on the beginnings of It’s Always Sunny in Philadelphia when she landed the role of Dee.
Before It’s Always Sunny in Philadelphia, Olson guest starred on shows like Punk’d, George Lopez, and Miss Match, and had a recurring role on The Drew Carey Show. She played a customer in Coyote Ugly too, but she was dreaming of a trainwreck character like Dee.
“I was grateful to be able to play a character,” Olson said on Basic! “This isn’t interesting anymore but back 18 years ago, or whatever it was, it was really hard to find a female ***hole who was just a total piece of garbage and was unapologetic. So it was a big thing back then where it was like yeah, but they have to be likable. These guys were like, ‘She doesn’t have to be likable.’ And I was like oh my God, so great.”
Dee has purposely gotten addicted to crack, found a dumpster baby and donned blackface among other inappropriate shenanigans. Her catchphrase is “God dammit” so that gives you an indication of her morals.
the gang cleans up nice for the Emmys. ? Krista Schlueter for @VanityFair pic.twitter.com/e2z2KFkWng
“Now they’re everywhere so you kind of take it for granted,” Olson continued. “That was brand new to me. I never had license to just yell and get creative with my insults and then not have to pull a punch and be like, ‘Just kidding, I’m just broken, that’s why I talk like that. Sorry, everyone.’ I was just a jerk and it was funny and it was so liberating and great.”
Even though It’s Always Sunny in Philadelphia is still on, Olson has had other shows. Fox’s The Mick parlayed her unapologetic persona. After nearly two decades of this, Olson is glad she gets to play someone a little different on Hacks.
“I get offered a lot of stuff that’s very similar to Dee or to Mickey, which I did in The Mick,” Olson said. “It was just so refreshing and nice to have a different character that was really funny but also raw and emotional, and just very different. I love that middle aged spoiled brat aspect of DJ.”