Discussions around the influence of the free software philosophy on art tend to revolve around the role of the artist in a networked community, and their relationship with so-called open source practices. However, one overlooked question, that is why some artists have been quickly attracted to the legal apparatus behind the free software model, is key in understanding the effect and interpretation of a free or open source work of art as a critical cultural practice. It is necessary here, to avoid a top down, all encompassing, and generalised analysis of the free culture phenomenon. We must instead take a closer look at its root properties, so as to allow us to break apart the popular illusion of a global community of artists using or writing free software, within an ever growing culture of sharing gathered around a vague idea of digital commons. This is the reason why a very important element to consider is the role that the license plays as a conscious artistic choice. Indeed, choosing a license is the initial step that an artist, interested in an alternative to standard copyright protection, is confronted with. Therefore this is the very reason why the first thing to do before discussing the potentiality of free works of art is to first understand the intention and process that leads to this choice. Even though such a decision is often reduced to a mandatory, practical, convenient, possibly tedious or fashionable step in order to attach a free or open label to a work of art, it is in fact a crucial stage. By doing so, the author allows their work to interface with a system inside which their production can be freely exchanged, modified and distributed. In this particular case, the freedom attached to a free work of art is not to be misunderstood with gratis and free of charge access to the creation, it means that once such a freedom is granted to a work of art, anyone is free to redistribute and modify it according to the rules provided by its license. What is more, there is no turning back once this choice is made public. The licensed work will then have a life of its own, an autonomy granted by a specific freedom of use, not defined by its author, but by the license that was chosen. Delegating such rights is not a light decision to make. Thus we must ask ourselves why an artist would agree to bind their work to such an important legal document. After all, works of art can already benefit, somehow, from existing copyright laws. Adding another legal layer on top of this might seem unnecessary bureaucracy. Unless, the added paper work might in fact work as a cultural comment, a form of artistic statement written as a contract, possibly a manifesto. If this is the case, what kind of manifesto and statements are we dealing with. What are they standing for? What are the effects of such contractual rules? What are their purposes and aesthetic consequences? Looking into such questions should give us enough clues on the nature and critical potential of free art.