Catching Up With Kit Williamson Of Mad Men And EastSiders

TV Features Mad Men

If you’re a fan of AMC’s Mad Men, you should already be familiar with Ed Gifford. Ed, played by Kit Williamson, is the shy, bespeckled copywriter, whose awkward attempts to please Peggy reminded me, at least, of my relationship with my mother. (Anyone else? No? Okay.)

Kit has already achieved remarkable success for someone his age. In addition to portraying Ed on Mad Men, he’s also appeared on Broadway with Liev Schreiber, and starred in a variety of independent films. What makes Williamson particularly interesting is that, in addition to his mainstream success, he’s also a pioneer for LGBT content. Last year he wrote, directed, and produced the award-winning web series, EastSiders. Originally launched on YouTube, EastSiders was later purchased by Logo, and aired on their website.

This year Williamson has raised over a $150,000 through a successful Kickstarter campaign for a second season. Paste caught up with Kit to talk EastSiders, Mad Men and the role new media can play in broadening the depiction of LGBT characters.

Paste Magazine: What was the inspiration for EastSiders
Kit Williamson: I really wanted to tell a story about gay characters with flaws. I wanted to tell a story about people in my neighborhood, people I could relate to. I wound up living in West Hollywood for a year before moving to Silver Lake. I’ve been here for a couple of years now, so it’s definitely my LA home, I guess. 

Paste: How would you say your experience living in West Hollywood compares to your time now in Silver Lake? 
Williamson: There was just a disconnect for me. It just never really felt like home. It was really nice and really convenient, and a lot of my friends live in West Hollywood, but it never really felt like my neighborhood. 

Paste: But Silver Lake feels more like home?
Williamson: Oh, for sure! I feel like I could stay in Los Angeles when I moved to Silver Lake. It very much reminds me of New York. But with all of the things—the advantages of living in LA too, you know? Being able to go to Target and load up your car. But you can still walk to the Farmer’s Market, and walk to breakfast and walk to your friend’s house. So, after living all over LA, I don’t take that stuff for granted. 

Paste: One attribute of EastSiders that I think is interesting is the depiction of sexuality. In more mainstream media, gay characters are frequently depicted as being really promiscuous. 
Williamson: Which is interesting because—certainly the characters at the center of the EastSiders could be accused of being promiscuous. But you’re right. Before the events of the show, Cal [the protagonist] had only ever had sex with his partner of four years. 

There’s a lot of diversity of gay men’s sexual histories. A lot of us still grew up in the shadow of the AIDS crisis. When I had my first kiss at sixteen, I convinced myself that I was at risk for HIV, from a kiss. I was a huge prude all through high school and most of college. I was afraid of intimacy. I was told as a kid that being with another man was dangerous and risky and scary. So, I waited. I wanted to represent that a little bit with Cal, as well. 

Paste: And then once things start collapsing with Cal and Thom, they do become a little bit more promiscuous. 
Williamson: But it comes from a place of hurt and need; holes in their relationship, and a disconnect between the two of them. 

Paste: Right, absolutely. What inspired you to make this a web series as opposed to an independent feature?
Williamson: I think that there’s a really cool, wild west sort of mentality to making web content right now. You’re allowed to make your own rules and distribute your content how you see fit, and tell your story in the way that best suits it. So, some of our episodes are ten minutes. Some of our episodes are twenty minutes. They aren’t restricted to the exact same format every single episode. And that was really liberating for me—to be able to set the structure and to let the show dictate the structure. 

I definitely knew I wanted to create a fully-realized character arc. I wanted to see Cal and Thom and their relationship evolve, and change over a course of a season. Allowing myself to have that goal informed the show and the structure. It’s been such a privilege as a writer and a filmmaker to be able to get to do something like that—to be able to block out these nine days in these character’s lives as opposed to making something so self-contained or a smaller story. A lot of shit goes down over the course of the first season. You’ve got a terminated pregnancy, you’ve got infidelity, you’ve got a relationship that goes through several different iterations of what a devolving relationship looks like. 

I think you really go down into the gutter with the characters, and hopefully climb back up out of it again. 

Paste: How did you get the cast involved?
Williamson: I wrote a lot of the parts with actors who I was friends with, or who I knew or had worked with before. I wrote John Halbach’s character, Ian, for him. I wrote Kathy’s character for Constance Wu. I wrote Paul for Sean Maher, I wrote Cal for myself. 

Then we got Van [Hansis] through an acting coach, Lesly Kahn, who we had worked with in the past. She recommended him and I was so thrilled that he got the script and was interested in doing it. We had open auditions for the part of Jeremy, and Matthew McKelligon just blew everyone out of the water and was the perfect choice.

Paste: I know that you used a lot of local businesses. How did you approach those vendors to be like “let us use your space.” 
Williamson: We shot at MJ’s and the Cha Cha Lounge….every local business that we approached was so amazingly supportive of us. The Cha Cha lounge right out the gate—I didn’t know anyone who worked there, I didn’t have any contacts there. But they were so responsive to the show, to the material, to the idea of doing an LGBT project. I think you just have to talk to people and explain what your goals are, and that you don’t have any money, but that you’re just trying to make something cool about the neighborhood.  The neighborhood really is a character. And people got on board with that idea which, is so cool. 

Paste: Did you have any new media inspirations when you were going forward or where there any sources you looked to get an idea for structure?
Williamson: It’s interesting because around the time that I was writing it, there was this general, common idea that said you’re supposed to have a shorter format for your web show. But more and more I’m seeing web shows break those rules to great effect and great success, and I’m excited to see what other rules we can break. The second they start to put new media into a box, it’s gonna break out of it. Because it’s slowly becoming just media. It’s slowly becoming just entertainment as opposed to this little niche of entertainment. I really love what’s happening on Netflix right now. I think House of Cards and Orange is the New Black are really changing the way people are watching television. Because you’re watching this show in its entirety; this thirteen hour movie. It’s really proven that people’s attention spans have expanded.

I was very interested in a lot of the shows that were coming up on Logo before ours did, like Hunting Season, and I’m a very big fan of The Outs, The Guild…. The Guild was probably the first web series I watched not exclusively on YouTube, but as a fan of a web show.  And I think it really changed a lot of people’s perceptions of what kind of audience was out there. It proved there was a loyal fan base and audience base for a web story. I’m excited to see the next thing that comes along. I try to watch everything that people forward to me. Anything and everything because you never know what’s going to strike a chord with people. 

Paste: Have you noticed whether or not there’s a new perspective emerging about gay relationships both in new media and in sort of traditional media?
Williamson: I think for a while, I was a little bit frustrated with the depiction of LGBT characters. I think it’s wonderful that there are gay characters on network television. I’m so excited to live in a world where you can turn on BBC or NBC or FOX and you can see a gay character represented or a gay relationship represented. But oftentimes these story lines are on the side of the main narrative so you don’t get to go in deep into the struggles of the relationship. Putting a gay relationship at the center of the story, I’ve really made it a goal to try and look at it from as many angles as possible.

Paste: I know you’re from a small town in Mississippi. How have people back home viewed EastSiders as opposed to your work on Mad Men? What has the reaction been?
Williamson: It’s been really interesting to have these two things happen at the same time in my life. People really gravitate towards one or the other, and the other becomes… you know, just a foot note. Part of a greater bio. I will say that it definitely seems like people in the south are much more interested in talking about Mad Men.
I don’t think that’s any kind of insidious homophobia I think it’s just that Mad Men means something more to a local newspaper in Mississippi than a web series does, whereas, people in New York and LA are paying a lot more attention to web content right now and what’s happening in that field.

Leland Montgomery is a Los Angeles-based freelance writer and contributor to Paste.

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