Samuel Cairncross first attended art classes at Wellington Technical College and took up painting seriously in 1942. In 1947, he was awarded a French Government scholarship to study in Paris, where he briefly attended André Lhote’s studio and visited galleries and other artists’ studios. He returned to Te Whanganui-a-Tara in 1948 having visited London and New York.
He worked as a part-time art teacher for adults in the Wellington area and specialised in street scenes at a time when other painters were more interested in empty landscapes. By the late 1980s, his work was keenly sought for its evocation of the buildings and fashions of an earlier era. His vigorous brushwork and bright colours put him among the Wellington Moderns, whose work was somewhat resisted by the mild realistic modernism of the Academy of Fine Arts.