This paper suggests a direction in the development of Surveillance Studies that goes beyond current attention for the caring, productive and enabling aspects of surveillance practices. That is, surveillance could be considered not just as positively protective, but even as a comical, playful, amusing, enjoyable practice. A number of recent trends suggest that there is a potential for unmistakable entertainment in the operation of a number of contemporary surveillance practices that merit further empirical and theoretical study. The paper discusses several examples that are illustrative of these trends, such as computer games and artistic presentations. Although this analysis does not downplay the problematic and negative features of current surveillance practices, it aims to accentuate some of the ways in which surveillance-enabling technologies are able to perform entertainment functions.