The Not So Straight and Winding Road

by Mikkel Hyldebrandt

Photo credits: David George Zimmerman, Wolfe On Demand, Jono Photography

Kit Williamson’s two-time Emmy-nominated LGBT series, EASTSIDERS, returns for a six-episode third season this month. Peach caught up with the handsome multi-tasker to talk about the new season, the American road trip, and reshaping cultural notions of relationships.


Mikkel Hyldebrandt: Eastsiders evolves thematically around relationship structures that are constantly being challenged. Is it your impression that gay people are more apt to try out relationship formats that go against societal constructions?


Kit Williamson: I think gay couples have different challenges than straight couples—not better or worse, just different. But it’s empowering to realize that in 2017 you can chart a course towards the kind of relationship you want—as long as both partners agree—whether you want your relationship to be monogamous, open or monogamish. I tried to represent that freedom in the different outlooks of the characters. In season 1, Cal and Thom are trying (and failing) at traditional monogamy, in season 2 they decide to open things up and in season 3 they’re questioning if the path they are on is really making them happy. The lesbian characters in season 2 have a much more open relationship, with very strict rules, and Quincy and Douglas have a pretty straightforward relationship with monogamy. I certainly don’t want the show to present the idea that there is a “right” way to be in a relationship, as every relationship is unique.


MH: The series’ characters struggle a lot with on the one hand conforming and behaving in an acceptable manner to overall society and on the other living an alternative lifestyle – do you think that is a common struggle associated with being gay?


KW: I think a lot of gay people can certainly relate to that—I know I can. Thom especially is a bit of a nonconformist, whereas Cal is a little more traditional. You get to know more about Thom’s background this season and find out that he was raised in a very religious family and is barely on speaking terms with his mother. He’s lost a lot, and values his liberty because of it—it came at a price. Cal, on the other hand, has a mother that’s VERY accepting, maybe even TOO accepting, and actually encouraged them to open up their relationship in the first season. We also get to see Stephen Guarino’s character Quincy struggle with expanding his idea of what a relationship looks like dating Willam’s character Douglas. In season 2 they have a fight over Douglas’ decision to go to a gallery opening in drag because he has a gig after, and Quincy has to face the fact that he might be harboring some internalized homophobia that’s creeping out.


MH: This season draws a lot of parallels to classic road trip movies – what is it that is so American about a road trip?


KW: Having driven across it several times, I can tell you that this country is VAST. There is so much empty land in America, still, and it’s both humbling and inspiring. You really get a sense of the possibility and the promise that this country represents when you drive across it, and you get to see firsthand just how differently people live state to state. I’ve always said the United States is a lot more like Europe


MH: Obviously, the season deals with making a journey – both literally and emotionally – so, tell us about what it is about this journey that makes this season of Eastsiders special?


KW: I think it starts out as Cal and Thom’s journey back to who they used to be—they know that they’re not happy, and they desperately want to get back to a place where they were. But they have to come to terms with the fact that they are fundamentally different people now and figure out what that means for their relationship. Quincy and Douglas are on a similar journey; only they feel stuck—literally, their convertible breaks down in the desert on the way to a drag gig in Cathedral City. And they have to muster the courage to take the next step together.


MH: You shot the season on location across the country from New York to California – tell us about that experience?


KW: It was wild, inspiring and incredibly challenging. I’m grateful for the experience, but I definitely never want to do it again! We got snowed out of Yellowstone, hit a stray tire on the road in South Dakota and shattered a window on the camper trailer in a freak storm. We lost locations because people googled the show and weren’t comfortable letting an LGBT project film. We met incredible, kind and supportive people too. Every day was surprising and a little terrifying!


MH: You raised money through crowdfunding to shoot this season. Do you think larger networks and production companies are still afraid to pick up LGBT-themed storylines?


KW: Absolutely. That’s just a fact. Things are getting much better in terms of mainstream stories that are inclusive of LGBT characters, but we’re very rarely allowed to be at the forefront.


MH: What was the particular thing you had to conquer personally to shoot this season of Eastsiders?


KW: It was such a huge undertaking, and it’s a miracle we got it done—we’re a really tiny team, and we don’t have a studio or network producing the series. In a lot of ways, the show has outgrown us. I’d definitely like to be able to bring on some help in the future!


MH: You are both behind and in front of the camera – tell us about the pros and cons of being on either side?


KW: It’s actually more challenging for me when I have to do just one thing at a time! I love multi-tasking, and I love problem-solving on the fly. Connecting all the disparate elements of a scene, from the writing to the blocking to the cinematography to the emotional life of the characters, is my favorite part of the process.


MH: Original content made for streaming is booming right now – how do you see the landscape of original content changing?


KW: I think we’re seeing an oversaturated market—there’s so much episodic storytelling out there right now, and the options can be overwhelming. It takes a lot for people to seek out a specific show instead of just stick with the streaming services they watch. That means it’s more important than ever to make sure your story offers something really unique and eye-catching, which is certainly something I aspire to.


MH: What are the things that makes this season of Eastsiders fresh and original?


KW: Taking five of the six episodes of the season on the road and shooting on location in sixteen states is something that a mainstream TV production just can’t do—it’d be a logistical nightmare. Because our set is more like a scrappy indie film we can offer something different from typical TV fare shot on a soundstage. And having shot the show now over the course of five years, it’s a really rare opportunity to get to see characters and relationships evolve over such a span of time—you can literally watch these people growing up through the season.


EASTSIDERS Season 3 will be available worldwide beginning November 28 on and Vimeo, as well as through various streaming services including Amazon Video, Google Play, and iTunes. The first two seasons of EASTSIDERS are available worldwide on Netflix, where they have been translated into a dozen languages.


Up Next!

Between the show and shooting a travel series for Out Magazine Kit Williamson and his husband John (who plays Ian on the show) definitely caught the travel, and have launched their own blog, Where Gentlemen Go, and they are releasing a video documenting their honeymoon in Europe and their trip to Life Ball in Vienna. We’re very excited to see where the road takes these two gentlemen!

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