Jake Silberman isn't supposed to be here.

If things had gone according to schedule, the comic—who was voted WW's Funniest Person in 2018—would have bid farewell to the city where he honed his standup and been an official resident of New York for nearly seven weeks by now. The plan was to hit the road for a tour with friend and frequent onstage collaborator Hunter Donaldson, recording footage along the way for a future documentary, and eventually settle for good on the other side of the country.

But in the era of the coronavirus, all plans have been ripped to shreds—which is how Silberman, who relocated from Minneapolis to Portland in 2013, found himself extending his stay in Oregon indefinitely, while facing a staggering confluence of ill-timed events.

In early March, just before Oregon went into lockdown, Silberman gave two weeks' notice to his full-time employer, for whom he wrote scripts, in preparation for the big move. Then every show he had booked canceled in a matter of days. Then his final destination, New York City, erupted with COVID-19 cases and the death toll skyrocketed. Then Silberman was denied jobless benefits because he quit—just a bit too early to know the virus would upend the economy and quickly push the rest of his department onto the unemployment rolls.

"Some bad luck, for sure," says Silberman, "but on the bright side—and I do try to think about this—I am really thankful I hadn't just moved to New York, because I would've been in a lot worse position."

Even though he's currently sidelined from in-person performances, you can still hear some fresh material on Silberman's new record, The Crowd Work Album, which debuted July 10 and features the comic bobbing and weaving like a prizefighter while jabbing the audience with jokes. The recording is one instance over the past four months when he lucked out—it was made in late February at the Funhouse Lounge, in the final days when people were allowed to gather in a confined space without worrying about spreading respiratory droplets.

We caught up with Silberman just after the album's release to find out what has helped him pass his time in quarantine.
1. Comedian group chats

We all do Facebook Messenger. Most hours of the day and night someone is on there talking shit to somebody. Since quarantine, I've started a few new chats, where we're keeping up with each other's lives and joking about everything—either local comedy scene drama or national news. I'm used to seeing these guys most nights, if not every night of the week. A big part of comedy is hanging out and shooting the shit with people. We try to keep it going through the digital stuff.
2. My bike

I try to go for a walk or two a day, but walking around the same neighborhood, it's, you know, the same scenery. So getting on the bike has meant a little bit more to me in some ways. Especially as the weather is finally turning nice, I'm planning on some longer rides throughout the city and potentially bike camping. It's weird, I used to have no time and couldn't do any of this and now I have all this time, but there's a deadly disease out there, so I'm trying to find a balance of making it safe.
3. Sugar

I have a major sweet tooth, and me and my girlfriend have been trying to cut back on it, but it's my only vice besides standup, honestly, because I don't drink, I don't smoke, I don't do any drugs. You don't really have a lot of outlets anymore. For me, I was used to going out literally every night and expressing myself. Now I don't really have that. Sugar is still this one little thing that I can control. It's a cheap outlet, but it is an outlet.
4. My friend's HBO Now password

I actually was able to lock down a password for pretty much all of the streaming services. I said HBO specifically because I've been going through The Sopranos for the first time. I'm on the last season right now. That has definitely been a late-night thing for me. I should be, like, reading more, but TV is just so easy to fill the hours with.
5. Scrabble

That is one of the very low-tech things that me and my girlfriend got into. I don't think I'd ever even played Scrabble before, and then we watched this documentary on the competitive Scrabble world. It's a game and a thing where you don't feel like you're killing your brain by zoning out and watching TV. And, for a comic, it's never bad to learn new words.
6. My partially finished new computer

I've always had old laptops, so I didn't really have a great computer situation. As things started to look like we're going to be inside for a while, I bought a MacBook, kind of hated it and returned it. Then Hunter Donaldson, my roommate and friend, was like, "Hey, I'll just build you one!" I'm not trying to sound like an asshole, because I do appreciate him putting it together, but there are some glitches. I'm kind of like, "You've done enough." So I called up a computer repair company to have them take a look. I don't know, maybe I am being an asshole…a little bit.
7. Applying for unemployment

Hooo, yeah. I've had a big journey. I was in a weird situation, because I did technically quit my job. It was very unfortunate timing. I've been applying for 13 weeks, and I finally got a call and they said, "Yeah, because you quit, even though you quit and then the world fell apart, you are not eligible." Honestly, it's so confusing. I can't believe how confusing of a process this is for such a terrible time in the country.
LISTEN: The Crowd Work Album is available on Amazon Music, Apple Music, Bandcamp, iTunes, Pandora and Spotify. $10.