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People like talking to Jake Silberman. Want to discuss your love life while you’re wasted in a Denver parking lot? He’ll listen. The former Portland comedy stalwart has a knack for getting people to open up—especially when they shouldn’t.
That raw, chaotic impropriety fuels Silberman’s new documentary, Back at It, which captures his ability to ad-lib in unpredictable company (whether onstage or approaching a stranger on the street, he scarcely sets down his microphone). Premiering on YouTube today, the film documents Silberman’s cross-country van tour in June 2021, watching as he observes America process, deny and party its way through politics and the pandemic.
Though Silberman moved away from Portland just two months ago, he’s spent this summer again crisscrossing the nation in his no-frills white van (and doesn’t take up official New York City residency until November). WW caught up with him to discuss his steely interviewing nerves, last summer’s distinct COVID-19 dynamics, and whether he still wonders about his film’s colorful road characters.
WW: Between this documentary and your Jake on the Streets web series, what have you learned about interviewing?
Jake Silberman: A lot of my style is to let [people] talk. I don’t try to interject my perspective. But it’s weird as a comedian because it’s like, “Should I try to make this funny? Or more documentarian?” That’s my biggest tension all the time.
Do you view impromptu interviewing as an extension of your crowd work?
Yes and no. You’re performing for the camera, which is much harder than for a live audience where you’re reading the room. I don’t think I’m great at it yet. But it’s a good skill to have, and people like living vicariously through video. I enjoy being at the heart of the action.
A lot of the interviewees in this film are 2 am drunk, but others seem to be going through real stuff. Do you still think about any of them?
Some of them! There was the moment in Denver where the guy got pretty upset about my Star of David [pendant]. It didn’t really offend me. It’s more like, “Man, what is this dude about that he’s so enraged by a dude wearing a necklace on a Saturday night?” It’s so funny too because I’m just this broke comic in a van trying to get funny interviews on the street, and he took it to this place where I represent all this shit in his life. I’m nobody, dude.
Have you always been good at tolerating discomfort?
Comedy obviously has helped that: hecklers, bad sets, whatever. But I was kind of a little shit-talker as a kid. I was the guy in my friend group who’d mouth off to somebody bigger. But there’s something about the microphone and the camera that gives it more of a “What are these people gonna do? Swing on me?” They know whatever happens is on camera. And I’ve found there is something about humans that they want to talk on camera and are OK telling a guy they don’t know personal shit.
When you reflect on summer 2021, was it a distinct social era?
That summer was unique because people were pent up. That summer, once you got vaccinated, you really did think, “This is all over for me.” So people were going out with that energy. And it was weird for [comedians]! Getting back on stage was so strange. When I was editing the doc, I was looking at how out of practice I was. I wasn’t in game shape.
As a comedian, what do you hope making a documentary accomplishes?
I’ve been doing comedy for over nine years, and it’s still weird for me to say I’m a comedian. You have that self-doubt. Now, I would never call myself a filmmaker, but I have made a film. It would be really nice if it opened a door to a job going around the country interviewing people—even if it wasn’t a comedy thing. I love talking to people, hearing their stories, going to new places. Now, I’ve been doing comedy long enough to know most things you do don’t lead to anything. I just hope it gets out to people who enjoy it and realize it was something we put a lot of effort into.
SEE IT: Back at It premieres at 9 am Wednesday, Aug. 17, at youtube.com/c/JakeSilberman.