With funding from two National Endowment for the Arts Grants, Stewart traveled the country photographing African American communities.

[6] As part of Kamoinge, an African-American photography collective based in New York, he traveled to New Orleans' ninth ward to photo-document the devastation wrought by Hurricane Katrina in 2005.

[7] He was an adjunct professor of photography at the State University of New York (SUNY) at Purchase, and served as a consultant for the National Urban League.

[9] For almost 50 years, he has photographed some of the most notable jazz musicians including, Miles Davis, Dizzy Gillespie, Max Roach, Sonny Rollins, Dexter Gordon, Lionel Hampton, Roy Hargrove, Marcus Roberts, and Wynton Marsalis.

Stewart attended School of the Art Institute of Chicago, and received a BFA in Photography from Cooper Union in New York in 1975.