Best subway portraitist - 2006
Orin is a kind of subway performer, but instead of singing or playing an accordion, he draws. That might not sound so entertaining, but when you have your portrait done on the sly and then presented to you with no real pressure to tip, you'll feel pretty special. Every morning, the baby-faced portraitist gets up and makes a T-shirt to wear that day, using markers on regular white undershirts. His designs are whimsical and cheerful, with things like butterflies and leafy branches creeping up from the hems. And his mood matches that aesthetic. Talking to his fellow straphangers, he is funny, friendly, and generous. Aside from the dollar bills his muses fork over, they give him a chance to perfect his work: studying the faces of Midwestern tourists, cranky old men, and bubbly young women on their way home from the office.