For more than fifteen years, art experimentations dealing with urban transformation have been increasing more and more. Artists are now influenced by places and urban planning. Urban planners turn to a new conception that implies more creativity and stances directly inspired by artists. Because of its flexibility, art is a negotiation and an innovation lever. Besides, it is part of urban, in situ, interpersonal relationships and based on process and context reality. Our hypothesis is that art meeting urban transformation creates new roles and figures prone to change the deal of how urban planning projects are made and how actors got organized. This paper, related to a French context, shows the figures’ emergence, identifies their cross-cutting skills, and explains the limits of this hybridization. By comparing two different case studies, we will analyze how these figures make the projects visible, and how they enhance depreciated areas in terms of individual and collective perception so as to include them in the rest of the city. With the art worlds, these figures appear at the core of artistic projects linked to urban renewal. They can perform roles either in an old or a brand-new way. With the urban worlds, they affect the actors game, modify the relationships and diversify the actors’ skills. By doing this they now look for legitimacy. We will start by presenting our case studies to identify these new figures. Then, we will see how the worksite specific context, as an art playground, enables to change the players game. Finally, we will show the limits and problems of these in-between figures