Descended from German immigrants, Leo Bensemann was born in Takaka in 1912. He attended evening art classes in the early 1930s although he is largely considered a self-taught artist. He had a long career with the Caxton Press Club where he worked as a typographer and graphic designer. Bensemann was also involved with the design and printing of two other prominent New Zealand publications: Landfall and Ascent. As a graphic artist, Bensemann designed initial letters, chapter headings, tailpieces and page decorations. His vivid pages portrayed strong elements of fantasy often incorporating mythical scenes and folk lore, as well as fables and the grotesque.
During the 1930s, Bensemann shared a studio at 97 Cambridge Terrace, Christchurch with prominent artist Rita Angus. He also shared a close association during this period with photographer Lawrence Baigent. All three were close friends and Angus and Bensemann completed a series of important portraits of each other during this period. Bensemann’s portraits often showed the subject in profile, juxtaposed against a landscape rendered in strong colours with hard edges in a style similar to Angus. Bensemann was also a core member of ‘The Group’, a coterie of New Zealand’s most important painters including Colin McCahon, Rita Angus, Doris Lusk, Olivia Spencer Bower and Toss Woollaston.