Kit Williamson On His “Mad Men” Role, His Web Series “Hipsterhood,” And The Benefits Of Being An Out Actor

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(Photo credit: Ali Levine)

Though out actor/director Kit Williamson has an unassuming eloquence and sly smile, he’s easy to find: He stars in the popular web series EastSiders, a Kickstarter-fueled Silver Lake drama costarring the lovely Matthew McKelligon, Van Hansis, and Stephen Guarino, as a droll romantic named Cal, as well as another web series called Hipsterhood where he plays a flannel-bedecked guy brimming with self-conscious inner dialogue. If for some reason you own a television, you can also catch him on the sinister nighttime soap Mad Men, where he plays Peggy Olsen’s nervous copywriter Ed Gifford. If you were Peggy’s underling, I assume you’d tremble in your spectacles too.

We phoned the busy 27-year-old during his first week of filming Anatomy of Deception, his new movie with Natasha Henstridge, to talk about his interest in Silver Lake pretension, his wardrobe on Mad Men, and his favorite gay flaws.

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The Backlot: EastSiders and Hipsterhood really zero in on Silver Lake culture in a big way. Are you constantly fascinated by these types of people, or do you occasionally burn out?

Kit Williamson: I would have to say that it’s a roller coaster ride for me as far as Silver Lake types go. Sometimes you just want to strangle the next hipster you see, and then on the other side of the spectrum, I’m so deeply with neighborhood and all the quirky, eccentric people that inhabit it. So I’d say it goes from day to day. Every day is an adventure. [Laughs.]

TB: Now everyone in the world knows what a hipster is. Does it bother you that everyone’s great aunt suddenly thinks she understands what a hipster is?

KW: I don’t mind the title [of hipster]. I think everybody is a hipster to somebody. I was born and raised in Jackson, Mississippi, and there’s not a person I know in LA who wouldn’t be considered a hipster to them. In that regard I’m very comfortable with the title of “hipster.” Comparatively in the neighborhood, I think I can’t really lay claim to being a genuine hipster compared to the other people I see and interact with on a daily basis. I’m way too simple to actually get tattoos. I have a boring hairstyle. And yet I wear cardigans. Is that really enough to qualify me?

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TB: Honestly, it might. Weirder yet is that your character on Mad Men could pass as a hipster today too. Those glasses.

KW: Totally. Absolutely. I only wish I could walk into a random vintage clothing store and have everything fit that well. That was one of the coolest things about going into fitting there. It was like going into a vintage clothing store where everything was your size. They have such impeccable taste in the costume department there that it took all the willpower in me not to pull the fire alarm and run out with the clothing rack. There are so many beautiful things I got to try on.

TB: The wardrobe people on that show have to be coronary-level intimidating. 

KW: Everyone is actually really, incredibly nice, but they’re really fastidious. Between every single take, your hair is adjusted. Your makeup is adjusted. Your clothing is adjusted. The props are adjusted. People are taking continuity pictures literally nonstop. And you know, that’s great. It keeps on your game in terms of deliver, not that you’d be anything but your utmost professional self when you walk on to a set like that. But the seriousness of purpose that the entire crew has, it inspires the actors as well.

TB: Mad Men examines retro values and behaviors; your web series couldn’t be more current. Is there any similarity between shooting Mad Men and your shows?

KW: I think it’s all the same process, but you’re dealing with more style elements, restrictions on characters and character behavior in Mad Men. That’s one of the reasons there’s such a definable tone to it. Everyone is in that world [on Mad Men]. There are societal factors, and it’s a workplace show too, so everyone on the show is wearing a mask — a number of different masks at the same time. That’s an interesting dynamic of that show, I think. As far as other projects I do go, it’s almost the opposite. Everyone is almost laid bare. There is no hiding who you are. They’re both equally fun for me to explore.

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TB: You had an amazing night at LA Weekly‘s Web Awards. Both EastSiders and Hipsterhood were honored. What was that night like?

KW: It was so cool. It was such a fun night at the awards since Michelle Visage and James St. James were the announcers. That was very cool, since I’ve loved them both from afar for a long time. It was totally unexpected for me that both EastSiders and Hipsterhood would win. That was mindblowingly awesome.

TB: The second season on Hipsterhood is available for binge-viewing. How would you say it’s primarily different than the first season?

KW: In the first season, there was actually no dialogue between the characters until the final episode. They were so self-conscious and too cool to talk to one another despite running into each other all over the neighborhood. The second season picks up the night after the first season finale. The ice has been broken, and they’re actually able to talk to one another and maybe go dating. But that puts them right back into their heads.

TB: We hear a lot about how coming out is detrimental to acting careers. What would you say are the perks of being an out actor?

KW: Well, I have a theater background. I started my career doing Broadway, and there aren’t many people in the closet there. They might not do interviews about it, but everybody knows everybody’s business. I think it’s kind of ridiculous to be a Broadway actor and be in the closet in this day and age. It obviously does not hurt you as far as casting goes. That said, I think you can make an argument that it does hurt you if you’re trying to be a movie star. I’m not trying to be a movie star, so I don’t have to grapple with that. I’m just trying to be a working actor. Thankfully we’re living in an age when some of those prejudices are fading as far as television and supporting roles in films go. What I’ll say as far as benefits in the media go, there’s already less of a barrier, less of a disconnect between content creators and audience. Lines of communication are much more open, and if you’re out, people are much more likely to reach out to you and connect with you on a personal level because they can relate to you. You’re not some capital-A actor who they don’t know anything about. You’re somebody they identify with. That’s something I’ve seen a lot with EastSiders; people relate to me and to a lot of the other actors in the show.

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TB: In the past when you’ve talked about EastSiders, you said that you wanted to explore flawed gay characters. In general, what are your favorite flaws of gay people?

KW: Oh God. [Laughs.] That’s tough, man! I think, taking it away from EastSiders for a second and talking about gay people in the world, it’s interesting to me how some gay people can be so judgmental. People who have to struggle with being unfairly judged their whole lives, they can sometimes lash out in a way that you think would be contradictory considering their life experience. It’s something I’ve actively tried to work against in my life, especially when it comes to other artists. I really just want to embrace people’s work and be as supportive as I can be. But man, there are some judgmental gay people! I think that’s pretty interesting. On a positive note, I think our flaws make us more human and nobody’s perfect.

TB: You’re shooting a movie called Anatomy of Deception with Natasha Henstridge. What’s that about?

KW: It’s a thriller about a serial killer targeting women who broadcasts his crimes on the internet. Natasha Henstridge plays a hard-nosed female cop and Miranda Frigon plays a D.A. They’re trying to track down a killer, and I play a tech expert who’s working with them. We’ve been filming for a week. Natasha Henstridge and I have some fight choreography that we’re working out! It’s an exciting, dynamic set to be on. I’m grateful to be a part of it. And honestly, Natasha and Miranda could not be nicer. They’re so fun to work with.

TB: Lastly, out of curiosity, what do you find easy as an actor and what do you find difficult?

KW: I’ve always found going to big, emotional places to be really easy. But the challenge is not to become self-indulgent. Just because you can cry doesn’t mean you should cry all the time. That’s something I try to be careful about, especially in EastSiders. It’s an emotionally turbulent character. He’s going through a lot, and he’s an emotional wreck. So I find the ways in which he’s suppressing that. And in all honestly, as a director I edit myself and take out some of the hair pulling, teeth gnashing, and floor pounding. This isn’t Greek tragedy. It’s real life. In real life we don’t want to feel things fully. Sometimes as an actor you can get too into the actual experience of feeling these emotions. That’s something I try to fight against.

TB: Well, remind me never to cast you in my next production of Streetcar

KW: No, come on! I can do that! I’ll weep, cry, pound the floor. “Stella! Stella! Stella!” But I want to play Blanche though.

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