Steven Phillips-Horst has had, like, a million jobs. He's produced music as Great Skin, he worked on Scott Stringer and Bill de Blasio's campaigns, and he hosts one of the only comedy shows in New York worth seeing. He also writes, directs, and stars in Trailing, our new favorite web series. "I'm a bit of a Renaissance man," Phillips-Horst deadpans over the phone on a break from his freelance copywriting gig. "I just try and keep my finger in every pot. I figure it's good to be not that great at a lot of things rather than good at one thing."
Phillips-Horst's dry, self-deprecating quality is the signature of Trailing's "gay anti-hero" Steven, an employee at a boutique political consulting firm with low-rent clients and a delusional boss; its banal absurdism is reminiscent of shows like Veep, Broad City, and The Office. The show's content pulls directly from Phillips-Horst's former life as a speech writer and social media employee at high-caliber political consulting firms. It's this insider knowledge that—along with a strong cast, slick production, and actually funny jokes—helps set Trailing apart. Here, Phillips-Horst tells us how to turn your shitty job into something worthwhile.
Can you tell me about how your background led up to the creation of Trailing? I did theater in high school. And I've always been gay, so that obviously helps. But I started doing comedy about two years ago, after I got out of politics. I had started writing this web series while I still worked at this crazy consulting firm that Bill de Blasio was a client for. At some point I realized I'm never going to have it that much together. I should probably try to just make fun of this world, rather than excel in it.
Were you sort of taking mental notes while you were still working there, or were you actually taking things verbatim? By the end of my time at the firm, I was just straight up writing at my computer; I would open a Word document and start jotting down ideas and dialogue and things like that. I wasn't totally dedicated to the job at that point. After I was fired, I started really fleshing out the scripts. I wrote ten scripts, we shot nine episodes, but we ended up only taking seven to completion because I wanted them to be really solid and special. There's a gazillion web series out there, so I'm trying to make this as good as it can be. I don't want to just push out content.
The third episode took me by surprise because it jumped from the kind of banal day-to-day of office life into a straight-up dream sequence. How does surrealism function on the show? Episode 3 has the most surreal moment but there are other little things—how her clients are not realistic, or when the boss gives him $400 to go to Chipotle to buy a burrito—that take it out of reality. Veep and 30 Rock, for example, have moments where the world feels real but there are moments that would never actually happen. I'm trying to create this world where it feels like all these different themes are possible.
A gay protagonist is already a huge defining step for the show. What representation of gay comedians do you hope to see more of? I do wish and hope that there will be more shows out there that can have fabulous gay characters that aren't just saying "Look! Gay people are just like everyone else!" I like the idea of shows where gay people are different and differentiated. My world is full of funny and fabulous gay people and I want to reflect that as a good thing.
What does Trailing add to the web series landscape? I hope it feels a little bit more complete of an idea, not just another web series. I hope that it feels like the singular vision of one person, but not just a vanity project. I also hope that the show has a broad reach. I know it's coming from my specific perspective, but I hope it's slick and accessible enough—even with its weirdness—so that people who don't normally watch web series or gay things would still want to watch it.