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Dylan Jenkins' first gig was at New Seasons.
Well, at Kennedy School.
Well, at the New Seasons holiday party, which was at Kennedy School.
It was Jan. 14, 2014, a date Jenkins spits out like it's his birthday.
Jenkins is a lifelong Portlander, born in his grandmother's house near Grant Park. He still lives in the neighborhood. It's his own little Mayberry—while settled in for afternoon drinks at the Hilt on Alberta, he sees two of his bosses and one of his roommates pass by.
While attending Benson High, Jenkins played in bands and started working at the city's favorite grocery store. Eventually, he hit a wall. His band broke up, and he gave up his bass guitar.
"My whole thing was, 'Man, I'm just going to be here until my band takes off,'" he says. "Then the music stopped. And I was like, 'I'm just going to be here a little longer.' And those two years turned into five and then into seven. Before I started doing comedy, I was living in a house where I didn't jell with the roommates anymore, and I kinda got into this funk. And then a friend of mine signed me up to tell stories at our New Seasons holiday party. At first I was pissed—people are coming up to me, asking me about it. I go find the sign-up sheet, and it clearly was not my handwriting."
But Jenkins quickly calmed down. A good friend had put him on the list, shoving him through a door he'd been too complacent to open himself—one that led to his current spot near the top of the local comedy scene, which has taken to his gentle, self-deprecating humor about childhood candy thefts, roommate drama and the perils of public transit.
"I'd wanted to do standup for a while," he says. "I'd watch the specials, and I was like, 'That looks awesome.' So I thought about it, and I'm like, 'I have two months, I can come up with a couple minutes of stuff.'"
And so he did—after procrastinating for two months minus one day and having a mild freak-out in the parking lot outside the party. He went first, and he killed in a room full of 200 co-workers.
"They were fish in a barrel," he says. "All I had to do was talk about shitty customers."
From there, Jenkins found his way into the next wave of the local comedy scene—his first show was Adam Pasi's showcase at Chinese Village on 82nd Avenue, headlined by up-and-comer Ian Karmel, who moved to Los Angeles soon after.
Here's how fast things move in Portland comedy: Jenkins has never actually met big-timer Karmel, once a fixture of the local scene.
Turns out, Jenkins had comedy in his blood.
"My father came up in the '80s comedy boom, with [2015 Funniest Five winner] Susan Rice and Art Krug and Dave Anderson," he says. "He stopped doing comedy in 1992, when I was like 3 years old, and moved back from Los Angeles because he decided he wanted to be a father and not be trying to film pilots in L.A. and not have a relationship with his kid."
Related: Susan Rice Is Portland's 2015 Funniest Person
Dylan's father, Robert Jenkins, was a professional comedian for 15 years, with screen time in Fright Night Part 2 and on Silver Spoons, MTV's Half Hour Comedy Hour and A&E's An Evening at the Improv.
"I found his tapes," Dylan Jenkins says. "I was in the basement, looking for porn, and I found a box full of tapes, and I was like, 'Oh, shit, this is dope!' I saw my dad's name on the tapes, and I was like, 'Oh, Dad was in porn? It's gonna be weird, but I'm gonna watch it.'"
Instead, it was a tape of his father on MTV. Today, they'll have lunch and talk shop—though more about the process and emotions than the practicalities of forging a career.
"My whole career has been on Facebook Messenger, getting onto shows. I've got GPS to take me to the venue," he says. "He's got all these stories of pulling out these big maps and driving to Billings, Montana, and having to change flats on the freeway…but the feeling you get when you succeed or fail with a bit, that will always be the same."
Jenkins' dad is retired from comedy. He drives a cement truck and happily owns a nice house off Mississippi Avenue. But Jenkins has gone on to get tutelage from his dad's old comedy buddies, including Rice, who was the first person to take him on the road, on a run to rural Washington. Jenkins bombed, but he learned a lot.
"I did 20 minutes for the first time, and I died a slow death. It was this big room in Milton, this big bar, and the people weren't sitting together or anything. Me and the featured comic were really having trouble," he says. "Susan goes up, and the first words out of her mouth were 'Go, Seahawks!' and the place erupts. I thought, 'That's a pro right there, I'm gonna remember that.' If you're up in Battleground, Washington, at the Main Street Bar and Grill, and something doesn't work, just say, 'Go, Seahawks!' and there you go."
Welcome to the Fourth Annual Funniest Five | Portland's Best Weekly Comedy Shows
No. 1: Adam Pasi | No. 2: Caitlin Weierhauser | No. 3: Dylan Jenkins |No. 4: Don Frost |No. 5: Amanda Arnold