This paper is an attempt to give an overview and to outline the main trends in the works of Italian artists of the past two decades dedicated to the characters of commedia dellarte. The new 21st century brought hundred-percent carnivalization to the society. Games and carnivals are related to work time and leisure, tourism and sport, shopping and catering spheres, politics and religion. It is no wonder that in this perception of the reality, artists again and again address the characters of commedia dell’arte, which served as personifications of the carnival for centuries. As before, the most popular characters are Harlequin and Pulcinella. Whereas Harlequin became a kind of a universal figure, Pulcinella remains precisely Italian. In recent years, the number of works devoted to the characters of commedia dell’arte is growing steadily. The artists are returning to forgotten plots and iconographic schemes of the previous centuries. Like their distant predecessors, contemporary painters use the characters of the Italian comedy to address current problems of their country, such as the environmental disaster of the ‘triangle of death’ in the south of Italy, the influx of refugees, and the loss of national identity. These characters have become symbols of Italian people. In parallel with the social context, the traditional interpretation of Harlequin and Pulcinella as the embodiments of creativity still survives. Furthermore, it is impossible to ignore the works related to the theatrical nature of human life and the world of fantasy and dreams.