Hamiltons paintings of the 1960s were frequently populated by figures. His subjects ranged from politicians and celebrities to anonymous crowds. His interest in these works always had as much to do with the people portrayed as with the mediation of their images through photography.
Portrait of Hugh Gaitskell as a Famous Monster of Filmland was intended to be more overtly political than Hamiltons Pop paintings. Hugh Gaitskell, leader of the Labour Party, opposed the campaign for unilateral nuclear disarmament supported by most party members. Hamilton enlarged a press photo of the politician to create a hybrid painting that drew upon images from horror films and pulp fiction.
After Marilyn Monroes death, Hamilton saw reproductions of a contact sheet of images taken by the photographer George Barris that she had marked and scratched. Moved by her violent obliteration of her own image, Hamilton incorporated the four photographs from the sheet into My Marilyn, with different painted gestures and erasures recalling Monroes.
Hamilton also looked at photographs of crowds on beaches and in cities and the way that a fleeting exposure taken at a random moment can reveal so many details of human activity. At a certain point of enlargement, however, the image would become illegible and degraded. Figures melted into amorphous blobs. The paintings based on excessive photographic enlargement sometimes recalled impressionism or biomorphic abstraction; more troublingly, the results also predict Hamiltons later interest in surveillance.