Born in New York, Gross began his career as a commercial photographer, apprenticing with photographers Francesco Scavullo and James Moore and studying with master photographers Lisette Model and Richard Avedon. His fashion and beauty photography has been featured in numerous fashion magazines over the years and his work has appeared on the covers of such magazines as GQ, Cosmopolitan, and New York Magazine. Celebrities Gross has photographed include Calvin Klein, Gloria Steinem, Whitney Houston, and Lou Reed.
His work has received awards from the The Art Directors Club and the Advertising Club of New York.
Gross was the author of a controversial set of nude images taken in 1975 of a then ten-year-old Brooke Shields for the Playboy publication Sugar 'n' Spice. The images portray Shields nude, standing and sitting in a bathtub, wearing makeup and covered in oil. Two of the images were full-frontal. In 1981 Shields attempted to prevent further use of the photograps but in 1983 a US Court ruled that the image did not breach child pornography laws. Gross sold smallish prints of the images for USD 625 each.
A photograph of one of those original photographs was produced by American artist Richard Prince, an artist famous for his "reproduction photography." Prince called his version "Spiritual America," after a 1923 photograph by Alfred Stieglitz that depicts the genitals of a workhorse. In 2009 "Spiritual America" was removed from the Tate Modern gallery exhibition called Pop Life: Art in a Material World after protesters described the image as "obscene" and a "magnet for pedophiles," although it had been shown New York's Guggenheim Museum in 2007 without incident.