The series comprises personal and professional photographs of Bill Boss, documenting his family and social life, career in journalism, and service in the Canadian Army. His family photographs include portraits and snapshots of his parents; the family home at 13 Ivy Avenue in Ottawa (New Edinburgh); his brother Mark's trip by train to Western Canada in 1943, including stops in Calgary and British Columbia; Mark's university graduation in 1944; and portraits of other relatives. The personal photographs include studio portraits of Bill Boss by Vincent Thomas of Ottawa; snapshots of Boss at social engagements; and photographs of him engaging in activities such as sailing, conducting symphony orchestras, walking in the North Downs, and sightseeing in the English countryside. There are also photographs of his friends John Monk, Alan Cowley and his wife Theresa, Stan Taylor, Patrick Keogh, Leslie Andern, Cecily Freeman, among many others who are not identified. There are a few photographs for his work with Ottawa newspapers, ca. 1938-1941, and a few dating from his time in Public Relations at the University of Ottawa.
The series holds a large selection of photographs from the wartime years showing his experiences in Canada, 1940-1942; England, 1942-1943; Italy, 1943-1945; and northern Europe, 1945-1946. His training in Canada is documented by photographs of Camp Petawawa in 1940 and the 4th Canadian Armoured Division in Debert, Nova Scotia, in 1942. The Debert photos portray RAM tanks, army trucks, bulldozers, the air station, soldiers at the Observer school, the visit of notables to the base, work parties, and training, including the assembly and launch of a temporary raft or boat. The Canadian Army campaign in Italy is shown both through his service as Public Relations Officer with the Canadian Corps and his work as a war correspondent for Canadian Press. There are a large number of portraits of individual soldiers, war correspondents, local interpreters, and civilians, most of which are unidentified. Some of the subjects of other photographs include Sicily in July 1943; Ortona; ruins of buildings; men of the Loyal Edmonton Regiment; the grave of Private F.R.E. Blyth; military cemeteries in Italy; Private Orval Campbell after an emergency operation at sea; and Bill Boss in the field for CP. In addition, there are photographs of Boss and a CP colleague sightseeing in Venice and Brennero, Italy. There are comparatively few postwar photos but these depict Fleet Street, London, 1948; Tony Phillips, 1948; Bill Boss in Konigsberg, Norway, 1949; a social gathering of war correspondents in French River, 1949; the Korean War, 1951; and Bill Boss covering French forces fighting in Indochina, 1952.
There is some overlap between the photographs and the negatives which is identified on the file folders, but for the most part they are separate and distinct images.