‘EastSiders’ Creator and Star Kit Williamson on Taking the Wheel in Season 3

‘EastSiders’ Creator and Star Kit Williamson on Taking the Wheel in Season 3
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Van Hansis, left, and Kit Williamson in “EastSiders.”

Van Hansis, left, and Kit Williamson in “EastSiders.”

It’s a bumpy road to love. But for actor and director Kit Williamson (“Mad Men”), making Season 3 of the two-time Emmy-nominated series “EastSiders,” out in full on November 28, meant settling in for the long haul.

Opposite an irresistible Van Hansis (“As the World Turns”), Williamson stars in this dark comedy about a Silver Lake couple who rise from the ashes of infidelity, red-hot. This season’s opening episode starring Willam from “RuPaul’s Drag Race” and Stephen Guarino from “I’m Dying Up Here,” Showtime’s new original series about the gilded age of stand-up comedy, made a splash on Saturday with its debut episode at NewFest’s For The Boys.

When “EastSiders” returns next month, the show will welcome back series regulars John Halbach (Williamson’s real-life husband), Constance Wu (“Fresh Off the Boat”), and Matt McKelligon (You're Killing Me), with the addition of Wilson Cruz (”Star Trek Discovery”) and Colby Keller (“High Maintenance,” also, your browser history, probably). Here, Williamson talks about directing his third season, his decision to hit the road, and what lies ahead for Cal and Thom.

Tell me about the choice to set this season against the backdrop of Middle America. There’s a romantic quality to the great American road trip that captures so well on film.

My husband John and I have driven across the country twice, getting our cars from our hometowns to Los Angeles, and I loved the idea of taking these characters out of their element and into Middle America. The focus is still very much on relationships, but I think being away from home gives them a new perspective on their own relationship.

I think the trip was shot in sequence, or maybe some of it? What sort of edge does that give you as an actor, to work in sequence to develop your character?

I wish we were able to shoot in sequence! We block shot all four episodes like a feature film — it was the only way we could get it done on our budget.

Stephen Guarino, left, and Max Emerson in “EastSiders.”

Stephen Guarino, left, and Max Emerson in “EastSiders.”

What does a drive through the heartland have in store for Cal and Thom?

Cal and Thom are between lives: They’ve fallen flat on their face in New York, and don’t know what’s waiting for them back in Los Angeles. Neither of them have a job or prospects of any kind, and they both sort of blame each other for the situation that they’re in.

Honestly, I think of this season as the last gasp of the characters’ 20s. They know they’re supposed to have their lives at least somewhat together by now, but they’re more of a mess than ever.

How does Colby Keller’s character come into play?

Colby’s character Arlen is in two episodes of Season 3, and he’s a really disruptive force in Cal and Thom’s relationship. They’re not on solid ground to begin with, and it may not be the wisest decision to bring a mysterious, handsome stranger with a great beard into the mix.

Let's talk about inspiration. Where did you draw yours from?

Every episode on the road is inspired by a different piece of Americana; Joan Didion’s essay “Goodbye to All That” about leaving New York, Thelma and Louise for reasons that will be obvious if you watch it, My Own Private Idaho and Steinbeck’s East of Eden. The Palm Springs episode is inspired by Priscilla, Queen of the Desert and the Silver Lake episode is inspired by Andrew Lloyd Webber’s Cats.

A scene from “EastSiders” Season 3, which debuted its first episode this weekend at NewFest’s For The Boys.

A scene from “EastSiders” Season 3, which debuted its first episode this weekend at NewFest’s For The Boys.

I love the scene at the start of Episode 1, when Douglas is sorting through these ideas and fantasies about growing up and what his life with Quincy should look like. Could you tell me a little more about when you came to work on that scene?

The whole concept for the episode sprang out of that scene. I wanted to let these fun, quirky characters have the kind of conversation we’re used to Cal and Thom having. [Douglas and Quincy] have been dating for a while now, but have kind of stalled out personally, professionally, and romantically. Their car breaking down in the desert is sort of a metaphor for that. They know they need to do something different, but have no idea what. The first step to fixing the situation, however, is understanding what’s broken. And in this scene, we sort of see them start to understand each other — and themselves — a little better.

For me, it’s interesting to watch the sort of dynamics that flesh out between these two, and in real time. In a lot of ways, I think this episode could be a standalone. As a director, how do you begin to capture what becomes a pivotal moment for these characters?

With actors like Stephen Guarino and Willam Belli, you just sort of get out of the way. They’re both hilarious, but there’s something really genuine and authentic about how they approach a scene. There’s rarely a false note with the two of them.

Another big difference between Season 3 and Seasons 1 and 2, is that the format has shifted. In the first two seasons, most episodes are written to take place over the course of a single day in the characters’ lives. In Season 2, I started to disrupt that a bit, allowing episodes to take place over two days or, in the case of our big threesome episode, over the course of an entire month so we can track the characters’ emotional development over the course of, I think, eight different sexual encounters. This season, every episode includes multiple time jumps, and we’re really capturing the characters at their most emotionally pivotal moments. It feels a lot more cinematic, which I think is appropriate for the setting — I wanted the road trip to feel like a movie, and the Palm Springs and Silver Lake episodes to feel like capsule episodes.

Stephen Guarino, left, and Willam Belli’s wig in “EastSiders.”

Stephen Guarino, left, and Willam Belli’s wig in “EastSiders.”

Tell me about your original memories of Palm Springs, and how you took them into shooting this episode.

The fact that Palm Springs is only a couple of hours away (depending on the traffic) is one of my favorite parts of living in Los Angeles. We’ve spent so many birthdays, anniversaries, and other special occasions there and that’s why we wanted to share it with our friends and family by having our wedding there. When the amazing folks at Burton House offered up their beautiful home as a shooting location, I jumped at the chance to write an episode to take place there. The landscape is beautiful, and I’m obsessed with the mid-century architecture and style of the area as well.

What is it about these characters and this world that keeps you engaged through the years?

Honestly, it’s the actors. I love writing for all of these incredibly talented people, and seeing the life that someone like Van Hansis can breathe into a scene is really inspiring for me. I also feel like the show has gotten so much better every season; I have a lot of affection for Season 1, but we had a budget of less than $30,000, and it was my first time as a filmmaker.

We’ve taken breaks between the seasons, mostly for budgetary reasons, but the show now spans five years of these characters’ lives. I love that kind of long haul storytelling, like Boyhood or Before Sunrise, where there’s so much history.

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