Shain Brenden's first set was on Christmas Day 2012 in Afghanistan.

Stranded in the middle of nowhere due to a sandstorm, Brenden and his colleagues found themselves re-enacting a scene straight out of White Christmas by staging a spontaneous talent show. But instead of Bing Crosby crooning comforting lyrics, Brenden was standing on a makeshift stage of crates lifting spirits by telling jokes. He realized early on after joining the Navy that comedy was a way of coping with the job's hardships.

"I was the guy," Brenden says, "who would be chain-smoking cigarettes, cracking jokes with my unit."

Brenden was always interested in comedy. He got a degree in creative writing from the University of Memphis, his hometown, with aspirations of authoring scripts for TV and film. But after graduating, he was working at a laser tag arena, facing 60 grand worth of student loans. The weight of that debt prompted him to enlist in the military, though he didn't score the kind of prime gig he was hoping for like his cousin, who was based in Hawaii and, as a military pediatrician, got to hand out stickers to kids. Instead, Brenden was assigned the role of combat medic and deployed multiple times to Iraq and Afghanistan, where he would crack people up in some of the most extreme conditions.

That Christmas, despite having no rehearsed set, he garnered some good laughs and was struck when many of his fellow sailors complimented and thanked him the next day. That impromptu performance became further motivation to pursue comedy once he returned to the states.

As soon as he hit U.S. soil—San Diego, more specifically—Brenden went to his first open mic. His initiation to the world of comedy was just like anyone else's. "It was God-awful," Brenden says. But with more stage time, he slowly began to gain traction. After the military, Brenden moved to L.A. and earned a master's in creative writing, but he took the opposite path of most comics by ditching the showbiz hub and relocating to Portland a year and a half ago.

"I left Los Angeles, which is the place where people go to try and make it for themselves and make it on TV," Brenden says. "And I was like, 'Fuck this town.' I left and I got here and I was like, 'Shit, everything I wanted to happen in L.A. is happening here—on a smaller scale, but it's still dope.'"

Now he's the jack-of-all-trades in local comedy—the "funny guy" on Trail Blazers Outsiders for NBC Sports, a star on the improvised, Old Spice-sponsored web series The Boardroom and, although he's reluctant to admit it, an actor. Brenden's home stage is at Mississippi Pizza, where he co-hosts the comedy show You're Welcome every Wednesday alongside Marcus Coleman and Adam Pasi.

"A half-black and half-Asian guy, a black guy, and a Samoan host the most popular free weekly show in Portland," he says proudly. And they have a lot of fun—the aim is to create a "hangout" space where you can grab a beer, a slice of pizza and tell some jokes next to a cardboard cutout of Queen Bey.

What Brenden likes about Portland is that it's the perfect city to build, both content and a career. It's his third comedy scene and by far his favorite. The performers are nice, the audience is nice, but with that, he's not afraid to say they can be "delicate" and "sensitive." People are willing to jump rabidly into the streets after one wrong joke. However, he also says Portland is a place that has any kind of comedy you might happen to be looking for.

Brenden's material is ever-changing, but always remains rooted in his personal experiences. When he was just starting out, for instance, jokes would focus on dating, video games and annoying roommates. You'll hear a vastly different set these days, but even Brenden has difficulties trying to keep up with himself—he says the content he wrote six months ago no longer feels relevant.

But right now, he admits, "a lot of it has to do with me dealing with how to be a 35-year-old guy, married, being a husband, being a father, but still feeling like a young idiot trying to figure it out. And I think that's just my whole thing: Am I a grown-up yet? On paper, yeah, I pay my taxes and I own a home. But I still feel like I'm just that undergrad dude that loves Family Guy and thinks farts are funny."