Three centuries have passed since copyright law was developed to stimulate creativity and promote learning. The fundamental principles still apply, despite radical developments in the technology of production and distribution of cultural material. In particular the last decades' developments and adoption of ICT's have drastically lowered barriers, which previously prevented entry into the production and distribution side of the cultural marketplace, and led to a widening of the base at which cultural production occurs and is disseminated. Additionally, digitalization has made it economically and technically feasible for users to appropriate and manipulate early works as method of production The renegotiation of barriers and the increasing number of creators who publish their works has led to an increase in copyright violations and a pressure on copyright legislation. Many of these potential violations are tolerated, in some cases have become common practice, and created social norms. Others have not been so fortunate and the law has been rigidly enforced. This arbitrary application decreases the predictability of law and forces a situation where creation relies on the tolerance of the other copyright holders. This article analyzes different cases of reuse that test the boundaries of copyright. Some of these are tolerated, others not. When regulation fails to capture the rich variation of creative reuse, it becomes difficult to predict which works will be tolerated. The analyzes suggests that as copyright becomes prohibitive, social norms, power and the values of the copyright holder dominate and not law.