Most people will have first met Kit Williamson when he starred as Ed Gifford on the Emmy-winning series Mad Men, but now he’s best known as the creator, writer, producer, and director of EastSiders, the Emmy-nominated web series about a group of LGBT friends living, loving, and often lying in Los Angeles. Its fourth and final season premiered on Netflix last year, and a new documentary about the creation and production of this seminal show was released last month.

EastSiders is for many Millennial gay men what Thirtysomething was to our parents in the 1980s—an honest look at our lives, our failures, and our world. This isn’t the sanitized version of gay life often presented in mainstream media. Williamson’s writing is fearless, tackling everything from toxic masculinity to STIs to, most notably,

nonmonogamy. In doing so, he’s created fleshed-out characters the likes of which are rarely seen on television but are frequently found in gay villages across America. This is a show by the queer community, for the queer community.

Kit Williamson was kind enough to answer some questions about his work on the show, from the roller coaster ride main characters Thom and Cal take over the course of four turbulent seasons to the importance of queer cinema to scene-stealing Kathy’s (Constance Wu) thoughts on Cats. If you haven’t seen EastSiders—and you really should—beware of spoilers below.

 

Skylar Baker-Jordan: First of all, congratulations on an amazing run and an amazing fourth season. How does it feel now that it’s over?

Kit Williamson: It’s bittersweet but the response has been really satisfying—we wanted to end things in the right way and I really hope that we did!

SBJ: I first watched EastSiders when it was on YouTube, before the first season was even complete. I was living in Chicago at the time, and spending a lot of time in London, and remember thinking just how authentic these characters felt. I hope you won’t bristle at the comparison, but really reminded me of Lena Dunham’s Girls—raw, unflinching, zeitgeisty—but for gay men. How important was it to depict gay men as we really are—warts and all?

 KW: I’ll take that as a compliment! Clifford (Jake Choi) actually tells Thom (Van Hansis) that his writing is like “The Velvet Rage as written by Lena Dunham for Modern Love.” One of the primary reasons I wanted to make the show was because I was frustrated with the ubiquitousness of unrealistically aspirational queer characters. It’s important to have role models, but equally important to tell stories about characters with flaws and complexities that blow up their lives and pick up the pieces. Otherwise, you run the risk of making people who make mistakes feel isolated and alone and broken compared to the perfect lives they see on TV. But we all make mistakes and we all feel isolated and alone and broken sometimes.

SBJ: So many of the actors are LGBT. Was this intentional, and did it add to the authenticity of the series?

It was absolutely my intention to create an unapologetically queer universe, because TV networks don’t seem to want to greenlight this kind of story. It’s great that we finally have a seat at the table in mainstream media, but it’s equally important to tell stories about issues that impact our community without worrying what a mainstream audience will think about those issues.

SBJ: Crowdfunding was so instrumental to the success of the show, but as you point out in the documentary, there are many limitations to producing a series this way. How is crowdfunding changing the nature of Hollywood—for better and for worse?

I think crowdfunding has allowed independent content creators to take their careers into their own hands—you don’t actually have to wait for the industry to give you its stamp of approval in order to go out there and make art. I don’t know what the long-term ramifications will be, but indie television is only growing; Sundance, Tribeca and SXSW are all programming episodic blocks and the market is growing.

SBJ: We’re both from the south (you’re from Jackson, Mississippi; I’m from rural Kentucky). I’ve since moved back south, but like you, I ran off to the big city in my twenties and found the experience liberating.  What would you say to LGBT kids living in Mississippi or Kentucky now, who might watch EastSiders and think “That’s the life for me?”

KW: I’m glad that I left but a part of me will always wonder how my life would have turned out if I had stayed. I now know many out, proud LGBT people who live in my home state and I’m absolutely in awe of them. The world is changing, even in Mississippi, and all of the progress we’ve made in the south is thanks to them.

SBJ: I find the road trip arc the most narratively compelling of the entire series, because it is so character driven. In the documentary, though, you talk about the struggles you had shooting the road trip scenes in season three, from homophobia to just simply logistical and financial constraints. Why was it important to you to take these characters out of the city and force them on the road despite how hard it was to film?

I really do want to Make America Gay Again. I was really inspired by the idea of staking a claim to the tradition of the great American road trip movie. If you’ve never driven across the country it’s hard to wrap your head around just how vast it is—this country is almost the same size as Europe, and the culture varies wildly from state to state.

SBJ: Speaking of the road trip, one of my favorite scenes is in episode 3×5, when Thom and Cal are sitting by the campfire. The episode is titled “Our Own Private Idaho,” so I assume you were conscious of My Own Private Idaho as you wrote, blocked, and shot the scene which mimics the famous campfire scene from that film (even down to the conversation Cal and Thom have, which echoes that of River Phoenix’s and Keanu Reeves’ characters in MOPI). How important has gay cinema been to your development as a filmmaker?

KW: I honestly don’t know if I would be here if I hadn’t discovered gay cinema. Representation is transformative, and it gave me the tools to envision a future for myself. It’s also given me a purpose—I hope my work can empower others the way that queer cinema empowered me growing up.

SBJ: One of the most relatable arcs, to me, is the struggles Thom and Cal have as artists—the ups and downs and the side hustles so many of us have. Why did you decide to make Thom, a writer, and Cal, a photographer, both artists?

 KW: Thom and Cal are both observers, struggling to make sense of the world around them as queer artists. This theme is really fully realized in their role in season 4—at this point they’ve worked through most of their issues and are really just debating the future of their relationship. It’s not really a question of if they’ll break up, just what kind of commitment they’re both looking for. And they’re watching the other relationships around them attempt to navigate these questions, just like the audience is. In many ways the final season is a dialectic on love.

SBJ: After three seasons of portraying Ian dating women, in season four starts seeing and fucking men (and we find out he has done so in the past). Why explore Ian’s same-sex attraction now?

KW: This storyline has always been something I’ve been interested in exploring, but I’ll

be honest that my hand was forced because Brianna Brown got pregnant and asked us to limit her involvement, and ABC wouldn’t release Constance Wu. It’s become a bit of a recurring theme that every season I’ve had to write multiple versions of the script for Ian. I’m really happy with how the storyline came out, and the feedback has been incredible.

SBJ: I want to talk about Quincy’s issues with Douglas and drag. I cheered when Quincy’s mom and later Ian asked him what he expected when he started dating Douglas. What was Quincy expecting his relationship with Douglas to be like, and why was this storyline—about drag and masculinity—important to you?

KW: When we first meet Quincy, he’s kind of the headliner of the parties that he throws, but as Douglas starts getting more and more successful as a drag queen Quincy gets relegated to booking his gigs. By season 4, he’s basically there to hold Amber Alert’s purse, and that’s hard for him. He and Douglas are also pretty different in that Quincy loves to play dress up in certain contexts, but also wants to put on boy drag and take pictures for Facebook. They fought about this as early as season 2, when Douglas wants to wear a dress to Cal’s gallery opening because he has a gig afterwards. I really wanted to explore something a little bit more complex than the typical “masc for masc” story, where the waters are muddy. Nobody would accuse Quincy of being a self-hating dude bro, but that doesn’t mean he isn’t worried what his mother might think about him getting married to a drag queen. We didn’t ask to be burdened with these kinds of insecurities as queer people—they were battered into us by society as kids. I wanted to examine the different ways people process with and work through those insecurities.

SBJ: One of the prevailing themes of the series is monogamy vs open relationships. Obviously one of the central struggles of the show is Thom and Cal learning to navigate an open relationship, but there’s less discussion (nuanced or explicit) about the pros and cons of monogamy. (We get a little of it with Derek and Jeremy in season four with regards to marriage and children.) Why was it important to you to show an open relationship, and is it a more realistic approach for modern couples?

KW: I think monogamy, even in queer relationships, is usually assumed to be the default, complete with all of the baggage of heteronormativity. Cal and Thom’s entire arc in season 1 is about them attempting to force themselves into a mold that they don’t fit. Jeremy and Derrick are kind of the opposite; their dynamic isn’t working, but it has nothing to do with either of them wanting to sleep with other people. I wanted to represent as many different kinds of queer relationships as I could to show that there is no one “correct” way to be in love.

SBJ: Jeremy and Derek have the most traditional love story of anyone on the show, ending up with the lovely home and even a child. In hindsight, it was clear from season one that Jeremy wanted just that. Is this sort of modern, urban love story—lonely gay guy falls in love with the handsome doctor, adopts a child, and lives happily ever after—a fairytale or do you think it can really happen?

KW: I loved subverting the idea of “the other woman” with Jeremy. Kathy even calls him “Jezebel” in season one. So having him end up in the most traditional partnership was a

fun arc to navigate. That said, I don’t think their story is a fairytale—they were on the verge of breaking up before the adoption went through, and like all the characters, they still have a lot of things to work through if they’re going to be happy. Otherwise Jeremy’s fear that he’s become a “Big Little Lies” wife just might become his reality.

SBJ: In season one and two, Cal is reluctant and uncomfortable opening the relationship, but by the end of season four it seems Thom’s the one having doubts about the arrangement. I never really believed that Cal was completely comfortable with it, though. Was he?

KW: I think Thom finally gets a taste of his own medicine in season 4—the problem for both of them isn’t really sleeping with other people, is poor communication and callous disregard for the other person’s feelings. When Cal throws up his hands and starts behaving like Thom, I think it teaches Thom how his selfishness has hurt his partner through the years. Everyone’s a little bit selfish—we’re all human—but you always have to consider your partner’s needs.

SBJ: One of the most interesting and frustrating moments of season four was, for me, when Cal wants to “make love” and Thom invites Jared over. I just wanted to shout at Thom “not now!” Thom is almost preternaturally incapable of reading Cal’s emotions or figuring out his needs. Do you think they were, as Thom later said to Cal, just “fuckbuddies” by that point, or was there still love there?

KW: I think people have an incredible ability to justify bad behavior, especially when they’re holding onto grievances. Thom was jealous that Cal got to act out a sexual fantasy on the day he was flying back from NY, and decided that meant he got to act however he wanted—but he’s not reading the room, and he misses a real opportunity for them to reconnect and work through their feelings. This really puts them both into a place where they aren’t communicating, and they don’t really hash things out until the second to last episode. I think they’re avoiding the subject because they love each other—we often avoid dealing with the real shit because we’re afraid of hurting the people we care about and end up accidentally hurting them as a result.

SBJ: The contradictions in Cal are really fascinating to me, especially this season. He was pissed when Thom hooked up with Clifford in New York but ends up doing the same thing with Logan a year or so later in almost a perfect role reversal. He says he doesn’t believe in marriage yet craves intimacy and commitment in a way Thom almost seems incapable of giving him. Both Thom and Cal are very complex characters and very well written. I guess my question here is can you explain to me where you think these contradictions arise from (if you even agree they’re contradictions), and why it was so important to show such layered and flawed characters?

KW: I think it’s important to take into account how much has happened between Thom/Clifford and Cal/Logan. Basically their “rules” have eroded so much that they’re almost nonexistent, so there’s no betrayal there—but Cal should obviously have considered how Thom would feel to come home and find him with another guy. Both Thom and Cal’s journey is really about them figuring out exactly how they feel about all of these issues—it’s possible to want opposite things at the same time, and that’s a tricky thing to navigate.

SBJ: I feel like I’ve bashed Thom a lot here, but I found him extremely compelling (and Van Hansis is just a phenomenal actor). Why didn’t we explore more of Thom’s backstory to discover what it was that made him so broken?

We hint at it a lot in season 3, in his scenes with Arlen the drifter in episode 3×02 and the campfire scene in episode 3×05. They connect in part because they’re broken in the same way. We don’t see a lot of Thom’s relationship with his family because he doesn’t really have a relationship with his family; the absence of those characters is intentional. That’s made him really self-protective, and there’s a fine line between self-protective and self-centered.

SBJ: Has Kathy seen the new Cats film and, if so, what did she think of it?

KW: She fucking loved it. And honestly, she could’ve saved that movie.

SBJ: What was your favorite or most memorable moment on set?

KW: The wedding was really magical; we had 100 kickstarter backers on set as extras and it was such an amazing full circle moment getting to meet these people who helped make the show exist.

SBJ: What’s next from Kit Williamson?

KW: Stay tuned! I have a movie and a new series in development that I can hopefully talk about soon. Mostly I just want to keep telling queer stories.

SBJ: Despite their love, Thom and Cal really have a knack for hurting one another. Do you think these crazy kids make it?

KW: It’s not about the destination, it’s the journey. They’ve loved each other through thick and thin for 7 years—to me, no matter what happens next, they’ve already “made it.”

EastSiders is streaming now on Netflix

Skylar Baker-Jordan has been writing about UK and US politics for more than a decade. His work as appeared at The Independent, Salon, Huff Post UK, and elsewhere. He lives in Tennessee. Follow him on Twitter or become a supporter by contributing to his Patreon account.