There is provided an image processing apparatus including a weight generating section that generates weight data in which a weight of a first region is larger than a weight of a second region, where the first region has a larger difference between a target image and at least one of a plurality of to-be-selected images than the second region, a calculating section that calculates a degree of similarity between the target image and each of two or more of the plurality of to-be-selected images with a difference between the target image and the to-be-selected image being weighted in each region in accordance with the weight data, and an image selecting section that selects, from the two or more to-be-selected images, one or more to-be-selected images that are more similar to the target image by referring to the degrees of similarity of the two or more to-be-selected images.