John Weiss first studied photography with Don Erceg in Cambridge before becoming assistant to Minor White at Massachusetts Institute of Technology (MIT) in 1969. He continued his studies at Rhode Island School of Design and obtained a Master of Fine Art's degree in 1973 under Harry Callahan and Aaron Siskind. Weiss was promoted to instructor and taught beginning and advanced classes at MIT from 1972–1973. He moved to Delaware in 1974 to become the resident artist in the New Castle County school system. In 1975, he joined the fine art faculty at the University of Delaware, originated what became a nationally recognized graduate program, and advanced the study of photography until his retirement in 2005. Weiss participated in numerous solo and group exhibitions throughout the United States and abroad and is included in private and public collections including the Museum of Modern Art, the Addison Gallery of American Art, and the Princeton University Art Museum, among others.
In addition to teaching and exhibiting, Weiss authored a monograph on the photographer Frederick Sommer and published a book of portraits and candid shots of major league players titled The Face of Baseball in 1990. Weiss began leading photo safaris to Kenya in 1997 and led 31 photo tours to Tanzania, Morocco, Spain, Italy, western Ireland, and Peru.