Randomness is being harnessed in the design of some interactive systems. This is observed in random blogs, random web searching, and in particular Apple's iPod Shuffle. Yet the role of randomness in design of interactive systems in not well understood. This paper reports on an empirical study examining the influence of randomness on the user experience of music listening. 113 instances of self-reporting were collected and analysed according to four themes: listening mode, content organisation, activities during listening, and affective outcomes. The analysis provides insights into how randomness is used to engender certain affective responses (such as feeling refreshed) by using various constraining techniques (such as playlists) whilst engaging in everyday activities (such as driving a car). The paper argues that randomness can be used as an innovative design resource for supporting rich and novel user experiences. Author Keywords Random, Design, User Experience, Digital Music, ...