[2] Bissinger's first connection to photography was when he was a stylist for the studios of Condé Nast Publications, where he developed relationships with some of the portrait and fashion photographers on staff, including Cecil Beaton, George Hoyningen-Huene, Irving Penn and John Rawlings.
He was part of group that shared a residence on Fire Island with Richard Avedon, who lent him a camera and encouraged him to take pictures.
[2] Bissinger developed an interest in the arts scene, photographing Truman Capote on the set of a film in Paris and Marlon Brando in front of a window in his New York City apartment.
A 1949 photograph taken at a table in the garden of Manhattan's Café Nicholson of the up-and-coming in the arts world included artist Buffie Johnson, ballerina Tanaquil LeClercq, author Gore Vidal, playwright Tennessee Williams and novelist Donald Windham, in what The New York Times described as "a class picture of the young and the talented in the American arts, more than ready for their close-ups".
He met Julian Beck and Judith Malina, founders of The Living Theatre, at a demonstration in the early 1960s and would take photos of the company's performances.