Early one morning, cartoonist Jack Kent sat aboard the Portland Streetcar, drinking a Monster energy drink, watching a quirky scene play out in front of him — a man was playing a video game, loudly taunting the screen.

With a spurt of caffeine and creativity, Kent decided to draw what was happening. "A couple days later I saw a guy at Starbucks with a ventriloquist dummy," he added. "Then I saw somebody eating pizza at the post office — all these things I’d never seen before that really made for unique moments."

And eight years ago this month, Sketchy People was born.

Let's rewind this origin story a bit. Kent first moved to the Rose City in 1999 to attend Mt. Hood Community College for civil engineering. Though his career eventually steered toward graphic design, "a nice blend of math and art," comics were an ever-present passion as far back as elementary school.

Today, his portraits of Portlanders are published by Willamette Week and compiled into annual books.

"Each sketch takes anywhere from half an hour to an hour on average," he said. "I do them at home so I can relax and get in my zone, but I’ve always got a small sketchbook on me to jot down a quick gesture if I can’t get a photograph." | Drawings by Jack Kent

"It’s fun because people watching is an art," Kent explained. "You start thinking about people beyond what you’re seeing at that moment. I think that’s a really important message."

As he drew, Sketchy People grew, becoming a community that told stories beyond the black-and-white pages.

When Yohhei Sato died in 2022, Kent offered to share his sketch of the well-known knife sharpener for a GoFundMe page to help Sato's family travel to their loved one's service.

"When his parents got back home they sent me a photograph of the shrine they built for him and my sketch is in there," he said.

Yohhei Sato was a fixture, often seen honing blades while enjoying a beer at breweries around the cit alongside his dog Spike. | Drawing by jack Kent

In another instance, the owner of a recently burgled music store asked if he could send Kent's drawing of a person pushing a shopping cart loaded with amps and instruments to the police.

“These sketches have connected a lot of people in more ways than I ever could’ve imagined," he said. "It’s been a really wild exploration, study, and learning experience on the human condition."