When Harry Richards and I sat down for our interview, the first thing he asked me was if I wanted half of his burger. You have to learn how to share, he explained, when you grow up in a big family like he did.
Now, Harry shares in a different way: through art. He started drawing caricatures for tips and donations near Saturday Market in Portland in 2010. He draws a lot of kids, he said.
“I ask kids what’s their favorite thing: race cars, dinosaurs, bears, ballerinas, unicorns,” he said, “and I take their face and I turn them into that favorite object. So they want to be a pirate on a ship, I draw a pirate ship then I give them a pirate hat.”
But Harry doesn’t just share his art with people who are willing to tip. Many of his subjects are poor or experiencing homelessness, so he draws them for free.
“I mean, I lived my life selfishly for many, many years being a drug addict. So now that I’ve been off drugs for over six years, I want to give back.”
Harry learned to draw in prison by doing scale drawings and looking at cartoon books. He’s come a long way since then. He now lives in a two-bedroom apartment with his nephew and nephew’s friend, and he has plans to convert the master bedroom into an art studio. He draws and paints abstract, architectural and spiritual art, and he sells it online with the help of his producer, who discovered him in 2008 and is currently working on a documentary featuring his experiences.
Harry has some specific goals for this documentary and a vision for a more ideal Portland. He also hopes that this documentary will help youth see that you can talk about things that matter to them. He sees the struggles that homeless youth face in Portland, and he hopes to make a positive impact in their lives. Harry grew up in poverty, sometimes splitting a box of macaroni and cheese among seven people for dinner when he was growing up. He wants to help youth avoid going through what he and a lot of other people went through, he said.
“I know what these children’s shelters offer,” he said. “They offer stuff, but it’s always ‘do this, do that, do this, do that,’ and that’s why they don’t work for most kids. And most kids have been seriously abused, molested by their parents, sold for drugs and being told what to do to have a bed. They’re not going to do that. To talk to a stranger about what’s going on and why they’re sad, they’re not going to do that, because they don’t trust.”
Drawing caricatures for money, however, isn’t a viable option for Harry all year round. So when he met someone selling Street Roots in November, he decided to try it for himself. Since then, Harry has brought four more people to Street Roots.
“It’s better than being dependent on other people and having no self-esteem,” he said.
Harry enjoys the people he gets to meet while selling papers, from doctors, lawyers and orchestra musicians to people from around the world staying in downtown hotels. “I like to intellectualize with people,” he said.
Harry encouraged people to seek out Street Roots as an income opportunity as well as an opportunity to connect with others.
“Even if you can’t trust right now, you’re still gonna make social friends, which can open you up to show that the world is kind,” Harry said. “All you gotta do is look at it from a Street Roots point of view, which is don’t judge and you won’t be judged.”
You can chat up Harry at his sales site, outside the Starbucks at Southwest Ninth Avenue and Taylor Street.