20 Questions with ‘It’s Always Sunny’ Star Kaitlin Olson

By  · Published on July 28th, 2009

If you watch her in an episode of “It’s Always Sunny in Philadelphia” or her role in the upcoming Weather Girl, you might conclude that Kaitlin Olson is an insane person. She seems incredibly comfortable playing characters who are tragic messes with supreme personal and drinking issues. We here at FSR can only applaud that sort of behavior, but it turns out that Olson isn’t exactly insane. She’s just a very funny comedian.

In Weather Girl (review forthcoming as soon as I finish the rest of these delicious cake balls that my roommate just made), Olson plays Sherry ‐ an insecure morning show anchor who is sleeping with the main anchor. That might be okay if the main anchor didn’t already have a live-in girlfriend. Who stands ten feet from both of them doing the weather on the show. Sherry is catty, shallow, and develops a taste for the bottle ‐ a recipe that seems to work perfectly for Olson’s sensibilities. At least the ones that have stood out on “It’s Always Sunny.”

Olson was brave enough to play our little game of 20 Questions in order to give us a better idea of her comedic style and what her experiences on Weather Girl and one of the most unethical shows on television have been like.

Q1: Would you consider your character Sherry unethical or just misunderstood?

Unethical, misunderstood and dumb.

Q2: The binge-drinking: was it method acting?


Q3: What draws you to that particular brand of comedy?

I’m drawn to the funny brand of comedy.

Q4: Do you think Weather Girl has a positive message for working women?

Sure! Don’t stay in a horrible job because it may seem prestigious when it is unfulfilling and suffocating. And you don’t force love. The greatest relationships are often the unexpected ones.

Q5: If you got into a fist fight with Sherry, who would win?

I would never fight with Sherry. I respect her too much.

Q6: Choose your super power: Flight or Invisibility.


Q7: How did your work on Weather Girl differ from your work on “It’s Always Sunny”?

It was a “bigger” and more sketch comedy-type character. It was really fun.

Q8: Do you find it difficult to find new ways to offend on the show?


Q9: If you were to play any historical figure, which one would you want?

Well, probably because of type-casting I’d have no choice but to play Mother Theresa.

Q10: Regarding “It’s Always Sunny,” what do we have to look forward to? What’s got you excited most about next season?

Dee stars in a movie, finally gets a boyfriend, the gang “wrestles the troops.”

Also, Danny gets naked.

Q11: What was your favorite movie from this summer and why?

Easy. Bruno. Because it blew my mind and Sacha Baron Cohen is my hero.

Q12: You’re acting in an upcoming project Leap Year. What are you liking most about the project?

Going to Dublin to shoot it, and working with Amy [Adams]. She’s a sweetheart.

Q13: Can you describe working with her and Matthew Goode?

I didn’t work with Matthew but Amy is sweet and fun and talented, and we had a wonderful time together! She was so cute when I showed up…she’d been in Ireland for months working with and surrounded by only men. When she saw me, her eyes lit up and she said, “another girl!!!” It was very sweet. We only worked together for 3 days, but it was a fun time and a great experience.

Q14: How different is Leap Year from your usual projects?

It’s a huge movie!

Q15: What’s up next for you?

I just wrapped “It’s Always Sunny in Philadelphia” today, and I plan on swimming, eating, being with my friends and family and having a wonderful summer. I’ll regroup in the fall and let you know what’s next.

Q16: What have you found encouraging/discouraging about building an acting career?

It’s an extraordinary and intoxicating sense of accomplishment and joy. It’s also a surprising generator of insecurity.

Q17: Do you think your career path is unusual? Do you have any advice for people trying to follow in your footsteps?

Don’t do it if you aren’t positive that you’re good at it! But if you know with all of your heart that this is your talent, don’t listen to anyone who tells you that you can’t do it.

Q18: Were you, by any chance, rejected from film school?

No. But I was kicked out of the Sunday Company at The Groundlings. But so are 97% of people who move through the program so it’s not nearly as exciting as it sounds.

Q: Is there anything particularly challenging about being a female comedian? Or a female actor for that matter?

Sure. People are often surprised that I can “hang in there with the guys.” I can’t tell you how many times I’ve heard that exact phrase. I didn’t realize how many people were expecting to watch me be mediocre! If I’m not careful it’s easy to get self-conscious, thinking I have cards stacked against me before I even open my mouth. On the other hand, I can choose to feel fortunate that I’m constantly a pleasant surprise. :)

Q: Is there something you’ve always wanted to tell the media/the public but haven’t been given a chance to?

Media: Why don’t you watch our little show?

Public: Thank you for watching our little show!

Related Topics:

Movie stuff at VanityFair, Thrillist, IndieWire, Film School Rejects, and The Broken Projector [email protected] | Writing short stories at Adventitious.