Paintings in which a work of art is the main subject occupy a unique position among pictorial representations. Unlike ordinary objects, these works of art represent an open field of meanings and interpretations that shift into the new painting, which in turn influences the reading of the original work – and thus, a network of interrelationships develops between the two. The “image within the image” principle first appeared in the Middle Ages. Its prominence increased during the Renaissance when the field of painting established itself as an autonomous discipline that defined its subject of interest outside the religious sphere. The field of painting, emancipated from its subordinate role, came to be viewed as an intellectual activity capable of satisfying the demands of cultured commissioners. As such, it could not avoid reflecting on itself – for example, on subjects related to the origination of a painted work of art (self-portrait, the artist’s studio), its “second life” (collections and galleries, a painting in a period interior), or the exploration of the limits of illusory representation (trompe l’oeil). The abovementioned processes of “the image becoming self–aware as a medium” gave birth to art as we know it today. The principle of the “image within an image” has survived to the present day, and it is interesting to watch how it reflects the changes in the visual culture. The most substantial of these was the emergence of the technical image, i.e., photography, photoreproduction, and later, digital media. And although the technical image has not replaced painting, it has managed to dominate our visual field. The exploration of the principle of the “image within an image” shows whether and how contemporary artists can combine the tradition of their field with the demand for an adequate grasp of their time by today’s means, meaning continuity with topicality.