Given the increasing complexity of living in a global village, countries and regions that are parts of larger political entities frequently have considered the option of separating or seceding an ideal solution to their problems with a larger center of power. Isolation, a form of “freedom from,” has the potential of offering them free rein or “freedom to” manage their affairs for their own sake. Francophone playwrights and filmmakers have found the dialectical interplay between “freedom from” and “freedom to” fertile dramatic soil for plays and films. Some of them work in both of these and other genres. These works seem to ask the same question: Is it desirable or possible to achieve both, even in ideal isolation, without suffering cultural stagnation or repeating the abuse of power on the part of the political center that led to the separation? This article explores the answers to this question given in the plays of Aimée Césaire, Anne Hébert, and Wajdi Mouawad within the greater context for this issue found in J. M. Coetzee’s Waiting for the Barbarians and Azouz Begag’s Un Mouton dans la baignoire and in francophone films by Raoul Peck, Bertrand Tavernier, Claire Denis, Rachid Bouchareb, Ousmane Sembène, Michael Haneke, and Mathieu Kasovitz.