Systems and methods of generating and modifying a playlist using contextual information are disclosed. For example, a user may provide an input seed such as a song name or artist name. The input seed is compared to database items and a playlist is generated as a result. In some examples, the contextual information is used to enhance the comparison and to select better content objects for a user's playlist. Meanwhile, in some examples the content objects in the playlist may be arranged in an enhanced order using ranking and/or contextual information.