In 1999 Friedman was one of five resident artists (including Byron Kim, Pauli Apfelbaum, Suzanne McClelland, Lorraine O'Grady) teaching at Skowhegan School of Painting and Sculpture in Maine. Friedman met John Waters, the visiting artist of that year, who later interviewed him for Parkett Magazine. In the interview Friedman spoke of his evolution as an artist over time, as well as the significance behind his art. On the humor of his work, Friedman said, "there's this misconception that playful thinking is not serious and it's not important."