Because Gregory Gillespie’s style varied so widely, he refused identification with a movement or genre. Gillespie began his career as a realist, but over time embraced symbolism and Surrealism, at times touching geometric abstraction and assemblage. The unifying thread in his oeuvre was its trajectory, following loosely the narrative of his own life and particularly his progression from youth into middle age; his grand project was to mythologize his own life. Gillespie painted a number of self-portraits, bare-chested and blemished, and portraits of his wife, whom he sometimes depicted as Venus or Madonna. His still life paintings often suggested intimate facts about his life, featuring the likes of personal post cards and tantric figures.