Previous research relating personality and music preferences has often measured such reported preferences according to genre labels. To support previous research, the current paper has expanded investigation of the relation between personality and music preferences to include direct measurement of music listening behavior. A study (N = 395) measured participants' personality, reported music preferences, and their listening behavior, which was tracked while using a music database for a minimum period of three months. Results indicated that reported music preferences were correlated to listening behavior, and indicated robust positive relations between Neuroticism and Classical music preference, and between Openness to Experience and Jazz music preference. Results also indicated issues when using genre labels to measure music preferences, which are discussed. Big Five, genre, listening behavior, music preferences, personal preferences, personality Numerous factors are involved when an individual selects a particular song, album, or genre of music to be played (Levitin, 2006). Arguably, these factors include, but are not limited to: emotions, personal experience, social context, and culture. Nonetheless, Levitin has stated that personality has a predictive influence over individuals' music preferences. Levitin's statement is Psychology of Music 40(4) 411-428 Keywords