Brave enough to mock his chubbiness and lack of phallic endowment (“I got cockblocked by my own body.”), Derek Sheen (no relation to Charlie, et al.) is building a body of work that's as towering as his own stature is diminutive: His albums include the lauded Tiny Idiot, Holy Drivel, and Disasterbation. Comedy fans may recognize similarities to the great Patton Oswalt both in Sheen's body type and delivery, which can spiral into barely controlled mania when the occasion calls for it—and it often does. Like Oswalt, Sheen is a master of self-deprecation, an ingenious storyteller, as well as being a keen observer of both his own idiosyncrasies and humanity's—on top of being a mercurial ad-libber. And Sheen's observations in the Holy Drivel track "Portland Vs. Seattle" will vividly resonate with denizens of both cities.

On Saturday, May 25 at Clock-Out Lounge, Sheen will be recording his forthcoming album, Macho Caballero (Stand Up! Records). In advance of the event, I asked him about depression and its effect on his work, taboo subjects, his favorite comics, and more... and I pressed him for a Trump joke. Interview after the jump.

The Stranger: In 2019, is the deck stacked against straight white male comics? Has the tide finally turned and a consensus formed to the point where people would rather get their humor from anybody other than those of your demographic?
Derek Sheen: Firstly, I don't think the deck is stacked against white males, seeing as how they've dominated the entertainment industry for so long and comedy has been one of the least progressive or inclusive areas. I'm sure white guys are probably trembling because they don’t get to run the game anymore, but we abused our privilege so frightfully, we deserve to have it taken away. I see comedy fans asking for more visibility from women, people of color, and the queer community while demanding a higher standard for white male comics and it’s about fucking time. I don’t see this as a threat, it’s making comedy so much better. It really is.

You talk about your depression and treatment of it in your act. Do you think that being on these meds has made you a better comedian, or is it harder to conceive great material on them?
I had a lot of misconceptions about anti-depressants and what they might do to my creativity, but what was really murdering that was my alcoholism. If anything, the medication made things much clearer, helped me focus better and eventually gave me a safer place to deal with my drinking, which quitting greatly improved my sense of humor.

What is the most important catalyst for your humor?
It's a tie between fear and stupidity! My sense of humor is really just a defense mechanism against both.

What’s a richer source of humor—mundanity or profundity?
Why can't they be equal? Even Einstein farted.

I’ve heard you diss Seattle for its humorlessness and describe it thus: “If you made a city out of a sad trombone, but also get that trombone wet and then filled it with white liberals who are also weirdly racist, you’d have Seattle.” Yet you’re recording your next album here. Do you have a love/hate relationship with the city?
Seattle is a unique city with a rich history and lush verdancy. Why, its vistas are almost as striking as its crumbling infrastructure and lack of empathy for the homeless.

I wouldn't say it's "love/hate." It's more like eye/roll. It's like raising a beautiful, strong child only to watch them become a Libertarian.

What topics will you never address in your act, and why? Or are taboo subjects for the spineless?
I don't believe anything is off-limits; it's really more about awareness of the consequences of your speech. What dialogue do I want to encourage? There are subjects I don't believe I'm qualified or entitled to speak on. I'm a white dude and nobody needs to hear my hot takes on race, feminism or trans rights, unless it's as an ally, but even then those aren’t my stories to tell. I've been fortunate to have some very patient non-straight/non-white friends help me get my mind right.

I know I'm a dinosaur and the world is progressing forward with or without me, but I would like to progress with it rather than angrily stand in place as it rockets by me toward a hopefully Trump-free future.

Tell us a joke about Trump and/or conservatives, if you would be so kind. You’re in a safe space here.
This one is my favorite!

Me: KNOCK-KNOCK!
America: Who's there?
Me: ...hopefully a military coup that drags that lying piece of shit onto the White House lawn and forces him, at gunpoint, to watch as the junta executes every one of his adult children...
...Orange you glad I didn't say "Banana"?

Who’s your favorite comedian of all time? Who’s your favorite comedian working now? I’d like reasons, too, if you could.
Yikes! Of all time? There's not one, it changes all the time depending on my mood. Right now, I'm digging on the late Dick Gregory. The first comedian my mom turned me onto, before Lenny Bruce (who does not endure the test of time, but that shouldn't diminish his legacy. The Beach Boys don't hold up well, either). He was an American treasure.

I also love Patton Oswalt, Maria Bamford, Brian Posehn, Ron Funches, Kyle Kinane...

The following are people I love to watch and who inspire me to be a better comic: (I would list reasons, but I think everybody should search them out and discover why they're so goddamned awesome)

Janelle James, Irene Tu, Arielle Issac Norman, Ian Aber, Johnny Taylor Jr., Whitney Chitwood, Kate Willett, Amy Miller, Jackie Kashian, James Adomian, Jo Firestone, David Gborie, Solomon Georgio.

And I would be remiss if I didn't tell you my favorite NW comedians: Clara Pluton (pleeeeease make them famous!), El Sanchez, Val Nigro, Natalie Holt, Claire Weber, Andy Iwancio, Alyssa Yeoman, and Erin Ingle all immediately come to mind as people you should go out of your way to watch before they leave.

Also, go support Brett Hamill and Emmett Montgomery's weekly, Joketellers Union and Comedy Nest at the Rendezvous. There are so many good people here right now.

What’s the one cliché about comics that rings truest to you?
"Comedians need constant validation" rings truest to me, but I don't know, what do you think?

What’s been your worst heckle and how did you deal with it?
Well, my entire professional career is most likely the result of my fourth grade teacher interrupting me during the semi-finals of the NW divisional Spelling Bee. I was almost through the word "electrocardiogram" when she stopped me at "d" to make a joke to the audience about how she might need an EKG from all the stress. The audience laughed as I continued to spell the word, starting again with the letter "d." "I'm sorry, electrocardiogram only has one 'd.' I am so sorry." It ruined me and I replay this in my head fairly often.

She died of heart failure three years later, by the way. Thank you, karma!

Please hype all your current/near-future projects and gigs as humbly as possible.
I'm recording my fourth comedy album, for Minneapolis-based Stand Up! Records, Macho Caballero, with Grammy-winning producer Dan Schlissel, on May 25 at the Clock-Out Lounge. My previous, well-reviewed, albums are available wherever fine streaming is... wait... shit. You said "humbly"? Fuck.

Also, tour dates are always going up at DerekSheenRulz.com.