“I have a thing for pigeons, it’s no mystery,” offers Stephen Powers (alias ESPO) by phone, when I ask him why he adorned our 100th issue cover with a phalanx of the world’s dirtiest birds. “Pigeons are urban dwellers, they’re the lowest common denominators, and yet they’re amazing animals that can fly 600 miles in a day and they’ll live off of anything. I love the fact that they’re so hated and despised but they run things.”

Pigeons somehow seem an apt spirit animal for the 38-year-old Powers, whose graffiti background has evolved into a body of iconographic work obsessed with urban truths, the underdog, and the search for meaning in this hard-knock life. Raised in Philly on a steady diet of soup, sandwiches, and spraypaint, Powers relocated to New York in August 1994. “The official answer I gave at the time was that I wanted to have a front row seat when the world was going into the toilet,” he says of the move, in actuality prompted by wearing out his welcome with the Brick City police force.

Throughout the ’90s, Powers committed his charisma and off-the-cuff sense of humor to paper, running the magazine On the Go–an experience that taught the former champion liar “not to promise anything, deliver what you say you will, and tell the truth”–and penning 1999’s seminal graffiti tome The Art of Getting Over. Since the dawning of the ’00s, ESPO’s personality-filled lettering has transcended the streets, appearing at NYC’s Deitch Projects gallery and the Venice Biennale. His recent time has been devoted to repainting Coney Island and making insane yellow plastic raincoats for the likes of Juelz Santana and UK grime MCs Jammer and Skepta.

“Don’t predict the future, report the news,” says the charismatic Powers when I ask him what his current motto is. “Everybody likes to talk about what they’re going to do. Discuss what you’ve done, or keep your mouth shut until you’ve finished something.” Never without a stance, Powers has an interesting list of idols that includes painter Henri Matisse, author J.D. Salinger, and Bob Dylan. “You can like Picasso because he was a master painter and technically really outrageous, but Matisse wasn’t bothered about that stuff,” he explains. “He just kept making beautiful things. Salinger was a total jerk and yet he was a devout believer in faith and love and humanity. And Dylan, in his way, did the simplest thing and made it seem so complex. I think that’s the trick. You do simple things and they get complex on their own.”