Sam Whiteley Wants You to Know About His Personal Failings

“I’m very imitable to a lot of my friends.”

Sam Whiteley seems to exist in a constant state of discomfort.

That’s most obvious when the 32-year-old comic has a mic in his hand. He moves around with a timid but endearing stiffness, shifting from foot to foot as he strains slightly to engage with the audience.

Adding to that is Whiteley’s ability to turn nearly every story he tells into an exploration of his personal failings. A regular joke in his arsenal begins with him mocking his former Pizza Hut manager who would send his delivery drivers out with this awkward maxim: “When you’re out there tonight on the road, just remember that our pizza is like sex. Even though it’s not that good, it’s still pizza.”

Whiteley would politely laugh every time but was left more confused than inspired. “I just don’t think that’s true,” he says. “At least in my experience, whenever I’m having really mediocre pizza, I don’t always feel super guilty because I know that it’s entirely my fault. Never had a bowl of Totino’s tell me it came just so I’d stop eating it.”

The Lake Oswego-born performer’s apprehension extends to meeting a journalist for his first-ever interview. Even though he’s on his home turf—Peter’s Bar and Grill on Northeast Fremont, a regular hangout for Whiteley—and warms up considerably as our conversation wears on, he never looks completely at ease. It’s something he’s very aware of, especially when it comes to his time doing standup.

“I’m very imitable to a lot of my friends,” he says, tucking into an early morning patty melt. “That’s still true, but it’s changed from shrugged-up shoulders and very little eye contact. People would make fun of me. ‘You can’t just read [jokes] from your phone!’ The charisma, I hope, has changed, but it’s never going to be animated.”

A lifelong comedy fan, Whiteley didn’t try his hand at standup until about nine years ago, usually only with friends who essentially dared each other to tell jokes at an open mic. Eventually, he started venturing out on his own, starting out at The Lamp, the bar connected to the Aladdin Theater that used to host regular open mic nights. From there, he’s been steadily branching out, landing gigs around Portland as well as scoring stage time around Washington and Oregon.

His momentum has stalled at times. The COVID pandemic temporarily killed the ability of most comics to perform in person, though Whiteley did participate in some Zoom gigs and a couple of outdoor shows.

More surprising is the time Whiteley has taken off from performing to coach high school basketball. For the 2018-19 season, he led the Lincoln High School’s JV squad and assisted with the varsity team as needed.

He may not be as hands-on with the sport any longer, but basketball remains a lifelong love for Whiteley. Even as he was absorbing the work of his favorite comedians in high school, he busied himself with doing the color commentary for the livestreams of Lake Oswego’s varsity basketball teams and poring over the box scores of the Blazers and the Oregon State Beavers.

Both have been continued obsessions for Whiteley, and he has a lot to say about the latter team during each episode of The Payton Years, a podcast dedicated to OSU basketball that he co-hosts with friend and roommate Andy Clark.

“He did it with a friend of his before that,” Whiteley says, “and I was one of their six listeners. I was like, ‘Dude, I gotta let you know, there’s so few people that are interested in Oregon State basketball on the level that you and I are, so thank you for doing it.’”

Whiteley has been part of the podcast since 2020, taking over for a previous co-host a mere week before COVID put a stop to every sporting event worldwide. (“I remember we did an episode the day they beat Utah,” he says, “and the next day, every college basketball season was canceled.”)

His and Clark’s hard work on the podcast and OSU has paid off in dividends, including scoring some great seats for home games and landing them some sweet guests like head coach Wayne Tinkle and current Blazer Gary Payton II.

Just how much time Whiteley can dedicate to the podcast may start to dwindle as he starts to venture farther outside the Pacific Northwest with his standup. Next month, he takes a major step in that direction with his first appearances at SF Sketchfest. Beyond that?

“I mean, no pressure,” Whiteley says, shifting in his seat and staring out the window a bit as he answers, “but it would be nice if comedy paid all the bills. I certainly wouldn’t seek out other work if I didn’t have to. Maybe it’s just because I went to L.A. [recently]. Although I didn’t do any standup or anything, just to be at the Comedy Store and to see, like, Chris Rock just walk in there and perform, maybe because I’ve seen it, it seems more realistic.”