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Don Frost thought the blind man was a mob boss.
"He was just sitting so still, wearing these shades," Frost says. "I kept making jokes, saying that guy runs the whole place. Eventually someone told me he was blind. I don't know why—I just immediately flung my water bottle at him. It whizzed right by his head. I said, 'Oh, I guess he really is blind!' That got a laugh out of him. I guess he felt it go by."
Frost is one of the only true road warriors in Portland comedy, a gray-stubbled 37-year-old who dresses in a way that seems immune to irony, with 13 years and many miles under his belt in dirt-track towns from Montana to Arkansas.
That blind man from the story? He was part of the audience at the Oregon state pen.
Frost teems with stories that seem lifted from episodes of Twin Peaks. In 2000, he moved to a Beaverton condo from Phoenix to grow marijuana. There, his friend's father—a former con man and leader of a cult devoted to aliens—slept on his couch and asked if he could have his submissive "sex slave" live in the closet.
After a traffic stop on a cop show made him panicky about selling weed for a living, he saw a rundown of open mics in "maybe the Willy Week" in 2003 and hurried straight from the laundromat with his socks still wet.
He won an amateur comedy competition in his first months of performing, but back then Harvey's was the only game in town. So instead of workshopping jokes to local scenesters like many of today's comics, he took his act on the road for weeks at a time—although he's had to shorten his tours since his 4-year-old son was born.
"I get known as the guy who can play any room," he says.
He's played an alpaca farm. He's been hired to make fun of welders on their lunch break. After Frost was hired to roast the attendees at a police and firemen's ball—whose guests apparently took themselves very seriously—he says a 70-year-old woman told him to fuck off midset. Every single person in attendance received a written letter of apology from the fire marshal, he says.
After another show, he cut down a tree with a chain saw for no particular reason. At another, a long-hauler let him drive a Mack truck drunk in circles around a Montana bar.
"Everybody was out front cheering," he says. "The gears were grinding. It's the stupidest thing I've ever done."
Frost will tell you, in seeming apology, that "weird things always happen to me." But like much in life, it isn't that simple. Frost's nature courts strangeness: He is disarmingly earnest, almost moony in his receptivity. You feel if you asked him to go shoot rats at the junkyard, he'd be up for it. He always seems confused and curious and surprised all at once—a stance that might be as much stage strategy as disposition.
Onstage at tiny side-street bar the Slide Inn on a recent Sunday, Frost stalked around the room grabbing bottles off of counters, giddy with existence itself. "Is this syrup?" he shouts. "Think of it. You're in a place where there's always syrup!"
Amid a Portland scene that can be so warm and insidery it's like a blanket fort for grown-ups, Frost may be one of the few comics in town who regularly encounters hecklers in the flesh.
One of the very first times he got onstage—at a comedy showcase at Dante's—a heckle from the crowd caused him to quit comedy for three months just as he was getting started.
"Nice tits!" a guy yelled as Frost took the stage.
"I just wilted," Frost remembers. People in the crowd started hooting at him, and he tripped over his lines—finally just giving up and walking off the stage. "It hit me in one of my biggest insecurities. I'm a man with boobs."
He didn't perform again for months. But after a friend advised him to own his insecurities as jokes, he hopped onstage with a series of boob jokes. Ever since then, he says, he feels "bulletproof."
But though he writes jokes, Frost admits he doesn't have the attention span to hone them relentlessly in the manner of a lot of career-minded comics—and so he's prone to improvisations and wild leaps and occasional crashes and burns.
"I was so dumb when I started I didn't even know comedians had an act," Frost says. "I saw a guy performing a second time, and I couldn't believe he was telling the same jokes. I knew people who were funny just talking, all the time. I thought that's what comedians did."
But this also leaves him responsive to whatever's happening around him. At the Slide Inn, he lapsed into revery about the Trump protests in Portland.
"I like to make a difference in little ways," he said, "even if it's just writing on the back of a cereal box at Walmart: 'Fuck Cheerios!' Or I'll draw a spider on a roll of toilet paper in a public restroom. People will remember that for the rest of their lives."
Don Frost is at Helium Comedy Club, 1510 SE 9th Ave., on Wednesday-Saturday, Dec. 7-10, and posts upcoming shows at donfrost.net.
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