On His DIY YouTube Series, Comedian Jake Silberman Plays Reporter, With Hilarious Results

He documents Proud Boys rallies, Trump rallies, and something called The Rally to Celebrate the Natural Heterosexual Family.

Jake on the Street

For years, Portland comic Jake Silberman avoided doing comedy on the internet. Then the pandemic hit, and he had no choice.

Lucky us: Silberman’s YouTube channel is goddamn hilarious, especially his Jake on the Streets segments in which he and cameraman Jesse Newell have gone out to document Proud Boys rallies, Trump rallies, and something called The Rally to Celebrate the Natural Heterosexual Family in Sandy, Ore., among other politically motivated gatherings.

Silberman, 34, goes a little easier on his subjects than Sasha Baron Cohen. Silberman is from Minneapolis, and besides dropping a few F-bombs, he’s Minnesota-nice. He asks questions and let’s people talk, and the results are by turns illuminating and hilarious, like the guy in a riot helmet and goggles talking effusively about the Grapefruit OG weed he likes to smoke, or the woman at an anti-mask protest (inside a Winco Foods in Salem) defending her position by arguing, “We have a right not to wear a mask and put our own lives in jeopardy.”

Silberman says he’s rarely felt unsafe at a right-wing event. But at left-wing ones, threats have been frequent.

While covering the occupation of the Red House on North Mississippi Avenue in September, someone with a gun told Silberman and Newell that there would be trouble if they didn’t leave. At a Portland protest against Joe Biden’s inauguration, demonstrators surrounded them and took swipes at their camera.

The far left and the far right both hate the media, Silberman says, but the right often uses that to its advantage.

“We stopped going to left-wing stuff,” Silberman says. “It wasn’t worth it. In their reality, I’m more dangerous with a microphone than other guys are with guns. It’s sad, but it’s true.”

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