The twentieth-century quest for individual freedom was pursued not merely in Europe proper but also at its boundaries. This had much to do, in the first instance, with a desire for liberation from metropolitan societies that many identified with an excess of constraints and conventions. It also reflected a strong sense of European superiority over both Americans and colonized peoples. But, as the century wore on, uncertainties arose from the growing power of the United States and the increasing criticism and various reforms to which colonial rule was subject. American popular culture appealed to youth across the continent, to the dismay of many adults, while colonized subjects increasingly claimed the status of free individuals, both in overseas colonies and as immigrants to Europe. This chapter discusses whether there was autonomy or conformism in America, at a time when its supposed freedoms were so attractive to many Europeans though they appalled others; how colonial self-reliance was loudly claimed and staunchly defended against indigenous demands and more liberal forms of European rule; and, finally, what colonized subjects’ perspectives were on the individual freedom they were denied but were seeking as part of their efforts to become decolonized.