A contemporary image is stored, is analyzed, and an associated data structure is generated. An image data structure may include image meta data, image classification data, image segment data, image caption data, or the like. The storage of the contemporary image is used as a triggering event and its data structure is used as an input to determine contextually relevant ancestral images. The contemporary image data structure is compared to respective data structures of ancestral images. A series of ancestral images are ranked based upon contextual similarly of their data structures to the contemporary image data structure. The most similar ancestral image is simultaneously displayed with the contemporary image. Interactions may be monitored, a prompt may be provided, a next ranked ancestral image may be displayed in place of the previous ancestral image, and/or a prompt to store a new contemporary image may be provided.