Stephen studied at the San Francisco Art Institute and received his BA from Bennington College. He has had solo exhibitions at 303 Gallery and the Julie Saul Gallery and group exhibitions at the Museum of Modern Art, New York; International Center for Photography, New York; and the National Museum of American Art, Washington, DC.

His work has been reviewed in the New York Times, Arts Magazine, ARTnews, Artforum, the Village Voice, and the New Yorker, portfolios have appeared in Artforum and the Paris Review. His work is in the collections of the Museum of Fine Art, Houston; the International Center for Photography, New York; and the Princeton University Art Museum.

He has received two MacDowell Colony Fellowships, a National Endowment for the Arts Grant and an Aaron Siskind Foundation Grant. He has been a visiting artist at the Donald Judd Foundation and twice been nominated for a Louis Comfort Tiffany Grant. His critical writing on photography have appeared in Artforum, Print, and Art on Paper. He was the Chair of the Graduate photography program at Bard College from 1998 to 2004, and has been the Chair of the Photography Department at the School of Visual Arts in New York since 1998. He is also the co-chair of the MPS Fashion Photography Program at the School of Visual Arts. In 2003, he founded the Auction for Photographic Education in Afghanistan to create a photography department at Kabul University. He is the co-founder of the Art+Commerce Festival in New York.

In 2007 he founded the photography magazine Dear Dave, and is its Editor in Chief.