Despite a plot that circles around infidelity, open relationships, and sex addiction, Kit Williamson’s Emmy-nominated web series Eastsiders waited until the recently released third season to show its first sex scene. Where other TV shows can be less prudish about on-camera coitus, Williamson gave himself a different set of rules to go by, given the fact that Eastsiders is a gay-centric show–and could expect to be held under a more scrutinizing microscope.
“I wanted the show to be taken seriously, so we didn’t have any sex scenes. I wanted to send a message clearly early on that we’re not in any way exploitative,” says Williamson, who is the writer, director, star, and producer of Eastsiders. “Now with season three, I felt like the show had grown up enough and earned the right to explore those subjects because they’re definitely important to the characters.”
Williamson, who played a young copywriter on Mad Men, launched a Kickstarter campaign in 2013 to fund Eastsiders, a dark comedy about boyfriends Cal (Williamson) and Thom (Van Hansis) who are slowly rebuilding–and expanding–their relationship after an incident of infidelity. Since season one, Eastsiders has moved from YouTube to VOD platforms and was released on DVD, garnering critical acclaim along the way.
From its inception, Williamson’s intention for Eastsiders was to buck expectations. He didn’t want to create sanitized characters for the sake of presenting the gay community in the best possible light, nor did he want one-dimensional caricatures. What Williamson was aiming for was the sweet spot in between for a more relatable truth–even if that means allowing characters to fall into stereotypes.
“Because people do fall into stereotypes. It’s one of my biggest pet peeves when people say that they don’t want to see feminine gay men on television or they don’t want flamboyant gay men on television or they don’t want LGBT people to be represented in ‘bad light,'” Williamson says. “I don’t want to have to shoulder the responsibility of representing an entire group of people that’s incredibly diverse. We have a shared experience but we are not a hive mind. So my initial goal with the show was to play off expectations–introduce what could be a very clean-cut morality tale of infidelity and upending that by allowing the characters to come at it from a more real, grounded place of not seeing things in black and white.”
The show’s most interesting arc stems not from the main characters but from Quincey and Douglas, played by Stephen Guarino and RuPaul’s Drag Race star Willam Belli. Acquaintances in season two, they soon start dating, becoming what most would consider an unlikely pair, with Quincey as the flamboyant sidekick of the friend group and Douglas as a sassy drag queen. Williamson’s keen dissection of gay dating dynamics–who’s the “masculine” one and who’s the “feminine” one and does that even matter?–is fleshed out in season two and comes to a head in the first episode of season three, in which the couple goes from fighting on the side of the road in a broken-down car to getting engaged in Palm Springs. It’s a bottle episode that adequately crams in all the emotional highs, lows, and grey zones of a relationship with two characters who could have easily served as mere fluff. It’s the best 30 minutes the series has produced so far.
“I’ve definitely learned the joy of writing for the specific actors,” Williamson says. “From the beginning, my plan with those characters was to introduce them as the comedia clown characters and reveal them as the lovers, upending your expectations and having the characters you think are going to be comedic relief have a lot of depth and a lot of shit going on underneath the surface.”
Williamson’s careful attention to character development could be what elevates Eastsiders into the class of Insecure, High Maintenance, Broad City, and The Trixie & Katya Show –which all began as web series and were picked up by cable networks.
“The best content out there is being made to be consumed either on premium cable or online from Hulu to Amazon to Netflix to HBO–those places are taking the most risks,” Williamson says. “It’s a bold, daring thing to put the full weight of HBO behind a single creator like Issa Rae, and it’s a risk that paid off wildly for them. But we don’t necessarily see network television taking that kind of risk. Oftentimes in network television, people get hired to do exactly what they have done in the past. If you directed an episode of a legal procedural, you will get hired to direct episodes of legal procedurals. HBO and Netflix and these other places are really taking risks on people–and fingers crossed that somebody takes a risk on me.”
Season three of Eastsiders is available worldwide through WolfeOnDemand.com, Vimeo, Amazon Video, Google Play, and iTunes.