Jake Silberman onstage at weekly comedy showcase Dough.
Jake Silberman onstage at weekly comedy showcase Dough. Suzette Smith

"The original plan was to leave in 2020," says Jake Silberman, sitting in front of Mississippi Pizza where he and fellow stand-ups Lance Edward and Thomas Lundy host a weekly comedy showcase called Dough. That night, they'd added a different comic to the stage, trying to see who would gel and be a good replacement for Silberman, as he plans to move to New York City at the end of June.

Silberman had gained a lot of momentum before the pandemic, structuring his sets around interactions with his audience—crowd work—which he freely describes as "a kind of improv." He had quit his job, prepared to move, and was on the verge of releasing a professionally produced stand-up special when the world hunkered down to stop the spread of the coronavirus.

In 2021, with very few live shows opening back up in Portland, Silberman began traveling to small towns around the Pacific Northwest, dropping in on any comedy show he could find. Those experiences are woven into his new material—where his previous crowd work had moved the focus off himself, much of his stand-up now revolves around funny things he saw and heard on the road. For instance, in his set at Dough, he related a strange, but not ill-natured experience of being the first Jewish person a small town audience member had ever met.

Now Silberman's finally making the move, cherishing his last month in Portland and the bountiful minutes of stage time that accompany nine years of hustling and hard work. He had very little experience when he moved to Portland in 2013, but caught a taste for stand-up from "a handful of open mics" in Minneapolis. He spent his first year in Portland riding around on a bike that was too small for his 6'2" height, doing two or three spots a night, and generally performing last—not a desired spot for open mics.

"I'm sure that hitting New York will be that all over again," he says. "Suddenly I'll be a tiny fish in the biggest pond." Silberman sat down with the Mercury for an exit interview.

PORTLAND MERCURY: Just before the pandemic it seemed like you really hit your stride with Crowd Work, both your special and the actual approach. Then we saw you hit the road. How has all that traveling and performing in rural areas changed your comedy?

JAKE SILBERMAN: The nerves are definitely less. I've done tiny towns in the Pacific Northwest, house shows, backyard shows—I just performed at a camp in Lincoln City for like 100 Jewish teenagers—and that broadened my sense of where I'm comfortable.

On the road, you get exposed to different kinds of people who will laugh at different types of things. You get to see a lot of different comics. One big lesson I took was that you have to be extremely funny, but you also have to find a way to stand out. You have to figure out what's unique about your work because there are a lot of really funny people out there.

Did you figure out what makes your work unique?
That is something I'd say I'm always actively thinking about. My bread and butter is crowd work. When it comes to written material, I would say I have a slightly dark viewpoint. I'm not trying to be edgy or shocking, I just naturally gravitate to a misanthropic tone.

Is there a subject that's too dark for you?
My philosophy about darker material is that anything can be made funny. However, the more sensitive the subject, the smaller the window is for it to be potentially funny. So a lot of people can probably write a good joke about their dog. But very few people could write a good school shooting joke. It can be done, but it's fucking hard.

And you're someone who works out most of his material in front of a crowd.
Right, I do most of my writing on stage, which means I bring an idea up—it's not really that well formed—and I just talk it out in real time, finding the beats and the punchlines right there.

What was it like not being able to work in front of crowds? Is that what caused your pivot to video?
I actually started doing these Jake on the Streets videos, for a local sketch comedy show, with zero plans of ever making them real. I would interview people in brunch lines. I filmed my Crowd Work special in, I want to say, February 2020, and I planned to move in June 2020. But then that all got put on hold. So when things started to open up again, I bought a van, and was just like: Alright I'm gonna do this.

Local stuff in Portland was still really limited, so I planned out a two month tour—one month with a camera guy—doing shows from Portland to New York City. Then I kept going down the East Coast, into the South, and through rural Texas. And that turned into another full-length special. It's not entirely stand-up—it's kind of a post-COVID road trip comedy. There are a lot of things in it.

When is that out?
I'm not quite certain of the date, but it's done and will drop soon. It's being produced by this company called Two by Four—they were also the ones who produced Crowd Work—and they're releasing it on this streaming service called Tubi.

Jake Silberman onstage at weekly comedy showcase Dough.
Jake Silberman onstage at weekly comedy showcase Dough. Suzette Smith

What's your take on the Portland comedy scene right now?
It feels very new. There are still a lot of comics that are very experienced and funny, but then there's also a lot of people who are in their first few years and still figuring it out. They'll build their own thing, and in a year or two it'll be their scene—whatever they build it to be.

What advice do you have for the comedians coming up now, with less experience than you?
I would say, the best thing to do for your comedy is get to know yourself. There have been times where I've felt worried or in my own head about comparing myself to others, and I've just found that to be a distraction and also an illusion. Once I really started to focus on my own work and my own page—so to speak—I can't even tell you how much happier I got. It's a really competitive field. You will go absolutely crazy if you start worrying about what everybody's getting that you're not.

Okay, the advice I want you to tell the next generation is: send emails, send photos, tell me about their shows. You're so good at that.
Yeah, that's a skill too though, and I think accepting yourself helps you promote yourself.

Speaking of promotion, tell me about this last show.
Hunter Donalson and I used to do these backyard comedy shows, so my going away show will be in a vein of that. It'll be outdoors—we're closing the street off so it'll have a block party vibe. Just literally some of the best comics in Portland doing tight short sets, and I'll host it. I couldn't get every comedian I like in Portland on the bill, but there's a good sampling of my funny friends. Anybody who follows the comedy scene will probably know them, but if you don't—fucking follow them.

Jake Silberman will host his goodbye show A Silby Send-Off with comedians Tory Ward, Shain Brenden, Seth Allen, Simon Gibson, Adam Pasi, Wendy Weiss, Dylan Jenkins, Jeremiah Coughlan, and Bryan Bixby at Desert Island Studios, 645 N Tillamook, Sun June 19, 7 pm, $10, tickets here)