The theme of this undergraduate thesis is the fragility and decay of cultural heritage, as well as the restoration and conservation efforts seen as symbolic healing of heritage. The current state of the Orlando’s Column in Dubrovnik, which despite numerous renovations remains damaged due to various disasters it has faced throughout its long „life”, inspired me to use the intertwined relationship between form and content through visual language to tell the story of the „afflictions that plague“ this medieval knight. The work depicts two recognizable scenes from the monument, while the third scene is connected to tourism and the popular series Game of Thrones, which was filmed in Dubrovnik. The works, executed in a hybrid medium of relief and painting, are made with a mixture that resembles human skin, thus personifying Orlando and highlighting the fragility of cultural heritage in need of treatment. The „unpredictable“ mixture has cracked, emphasizing both literal and symbolic cracks. The realization of the work was preceded by artistic research, the process that is highly individual and experimental, as it allows maximum freedom in artistic interpretation and visualization.