Inspired by legendary artists like Saul Steinberg and Robert Searle, not to mention his years as a professional skateboarder, Russ Pope’s gestural characters and scenes capture the humor, intimacy, and unpredictability found in everyday life. That unique perspective, plus his artwork’s powerful ability to connect people, made him the perfect artist to illustrate Cole Haan’s celebration of progress this fall. From his home in coastal New Hampshire, Russ spoke to us about everything from the rabbit that kick started his career, to his number one rule for young artists.

“When I was five years old I went to kindergarten, and at kindergarten we had an exercise where we were all supposed to draw some Easter themed drawing. I remember as a five-year-old I drew this rabbit. My mom came to pick me up. The teacher hands you—literally delivers you by hand to your mother—and says, ‘Russell, is a really great artist. Look at this beautiful rabbit drawing, this bunny that he drew.’ And I was like, I’m an artist…she just said it, I’m totally an artist.”

“You know, there is always something that happens at dinnertime. Sometimes when I’m exhausted, it just becomes a photo that I draw that night when I get back and I’m having some drinks. But at lunch I’m always drawing. I’m sure my family, when they’re with me, are sick of me looking at them and making drawings of them eating and drinking and stuff, or of the area.”

“If you asked me ten years ago I would have said, it’s just s—t. But I do know for a fact, because of the daily reminders from people, how much it means to them. I think it’s very special, and I’m very grateful that I can do something that brings people joy. And whether it’s overt or not overt, I can look back to the work and it brings me back to that point in time when I was inspired to make whatever it was. Whether it was from a trip to Lisbon with my family or a trip to Moscow in a van loaded with eighteen skateboarders.”

“That for sure came from skateboarding and the zine culture. To me, it’s an easier, quicker, more realistic way to communicate with each other. And it really was just because there wasn’t, you know, text or DM or anything like that. That’s how I met people as a skateboarder. We’d exchange addresses, give stickers from the companies that we skated for, and we’d be fast friends forever. I still exchange postcards with a chunk of those people today. It’s wild.”

“When I was five my dad made my first skateboard, he hand-built me this board and painted it. We went to this toy store that doubled as a skate shop and bought non-sealed ball bearings that he pressed in and a sheet of grip tape. And then I never stopped skating. My mom would take me to contests and drop me off when I wasn’t old enough to drive…Santa Cruz, Derby Park. I’ve been skateboarding since I was five and started traveling for contests and demos when I was 14—and now I’m 50.”

“I had an art show and I literally took money from one of the paintings that sold and I bought a run of boards. And they were gone instantly, and it just kept on getting bigger, and it still is. I just signed a new two-year deal with a distributor in California that’s licensed it, and with me in complete creative control, and I will continue to retain ownership of it.”

“This was really interesting because Cole Haan came to me and it was an opportunity to be able, through drawings, to show people being with people again, and cities being cities again. You know, like being able to draw cities that were populated with folks and people sitting on park benches together, cause that’s actually happening again. And it’s cool to be able to do that, like celebrate freedom without sounding corny. Celebrate freedom, celebrate optimism, celebrate new thoughts and ideas.”

“This was really interesting because Cole Haan came to me and it was an opportunity to be able, through drawings, to show people being with people again, and cities being cities again. You know, like being able to draw cities that were populated with folks and people sitting on park benches together, cause that’s actually happening again. And it’s cool to be able to do that, like celebrate freedom without sounding corny. Celebrate freedom, celebrate optimism, celebrate new thoughts and ideas.”

“La Fontaine de Belleville [in Paris]. It’s cool. They play jazz music there a couple nights a week. They have a nice little set of classic cafe tables, not too deep, not a packed tourist trap; the locals go there. They also have a full-service bar, so they can make you a spritz or a negroni for breakfast, if you want that. So anyway it’s a good place to go and get juiced up with coffee before you transition to spritzes all day.”