A system and method are provided for mixing song data based on measure groupings. A player or program may recognize measure groupings in a song through identifying cuepoints. The player or program may use the cuepoints and/or other identifiers of measure groupings to generate a transition between the song and other songs. Parts of one or both songs may be time-stretched, or frames may be added or deleted, such that the beats in both songs are substantially aligned during the transition. The system and method may also involve altering the sequence of frames in one or both of the songs, so that the transition may have various sonic qualities as desired by a user. A choice of transition modes may be provided via a user interface that allow the user some control over when and how transitions between songs are executed.