Our Annual Best of Portland Issue Is Dedicated to the Small, Inspired and, Yes, Weird Ways People Have Made Their Lives Here

A city is what you make of it.

When I moved to Portland in 2008, it wasn’t to live the dream of the ’90s or slack off into early retirement or any other cliché—I just needed to get out of my hometown.

I was 25, with no job, no friends and only a vague plan to eventually worm my way onto the staff of a local alt-weekly. Over 13 years, I met my wife, had a kid, fell in with a great group of people and, well, you can see how the newspaper thing turned out.

In between, there were hundreds of nights at dozens of different bars. I spewed red corn syrup in my roommates’ faces for a “zombie prom” none of us even remember. I got the worst sunburn of my life floating the Clackamas. I saw Dave Chappelle bring half the damn city to Pioneer Square for a show that never happened and stood 20 feet away from Prince at Roseland Theater.

Sorry to make this about myself. But then, what is the measure of a city if not millions of individual experiences playing out at the same time?

Our annual Best of Portland issue is rooted in the idea that to truly understand a place, you have to dig beyond the prevailing narratives and find the small, inspired and, yes, weird ways people have made their lives here—like the former weed dealer who started a cannabis-themed magic show. Or the guy named Jesus Christ—no, for real—who found salvation riding through downtown on a cross-shaped skateboard.

It’s been a rough 16 months. But through the wildfires and ice storms, the heat and the tear gas, Portlanders have continued to look out for each other, whether through odd community projects, like converting this paper’s old boxes into miniature Blockbuster Videos, or starting a whole new business, such as a ride-share service tailored to the most vulnerable passengers.

Our Readers’ Poll is itself a testament to how the city reacts to tough times: We asked about the best local responses to the pandemic, and readers voted en masse.

I’ve been thinking about the experience of living in Portland because mine is ending—this is my final issue at Willamette Week. I’m moving with my family to Tucson, Arizona, to see what we can make of that place.

I’m leaving at a time when the debate over the city’s future is raging louder than ever before. Is Portland dying? Is it already dead? Or is all the hand-wringing overwrought, and things are both as good and bad as they’ve always been?

All I can do is speak for myself: I’m going to miss the hell out of it.

—Matthew Singer, Willamette Week Arts & Culture Editor (2012-2021)

Click here to see more Best of Portland 2021:

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Click here to view the Best of Portland Readers Poll 2021 results.