David Cowles was born in Rochester, N.Y. in 1961, the last of six children. His father, Hobart, was a Professor of Ceramics at Rochester Institute of Technology, and his mother, Barbara, was manager of Shop One, a Rochester gift shop heavy on the crafts.
Cowles landed a job at the Democrat and Chronicle in Rochester in 1983, and began his freelance career two years later, leaving the paper to work freelance full-time in 1991. Cowles' work has appeared in Entertainment Weekly, Rolling Stone, Vibe, Time, Newsweek, Playboy, People, The Village Voice, Money, Worth, Fortune, Fast Company, Los Angeles Magazine, New York Magazine, The Boston Globe, The Chicago Tribune, The New York Times, The New Republic and Vanity Fair, among others.
Cowles has worked as a creator, designer, storyboard artists and director on animated projects for Disney, Sesame Street, They Might Be Giants and Frederator Studios, among others.