Our active lifestyles see us playing, pausing, and skipping through life all the while our phones are in our hands. For many, completing the daily grind requires regular audio and visual media accompaniment and for this we interact with our phones as we skip, run, and jump. In this respect, a unique form of digital library is our mobile media player of choice. These media players serve as both the interface for listening to and watching these audio and visual media as well as the media library and storage. We argue therefore that the interface design considerations of the media library as well as the media interaction require user centered investigation. We tested button placement variations and analyzed the user preferences as well as user interaction with these mobile media player prototypes while on the move. Early insights suggest users prefer what they are most accustomed to, yet issues of accuracy with interface designs that are unfamiliar require further investigation.