A content management system and/or client device can enable a user to initiate a quick play mode where a content category and content medium are selected for the user. A client device and/or a content management system can select a content medium for a user based on one or more factors, such as the content category. Certain content categories of content can be preferably delivered in certain content mediums. In some embodiments, a content management system and/or client device can select a content medium for a user based on contextual data gathered from the user. Contextual data can be data describing the user's current state and/or environment. For example, contextual data can include data such as the time of day, geographic location, etc.