In this paper, we present two studies (Singaporean university students) that show cultural tendencies, particularly Analysis-Holism differences in thinking styles (Choi et al., 2007), affect mood regulation benefits from music listening. Study 1, an exploratory study, selected strong cultural tendencies associated with mood regulation in music. Participants (N = 127) completed measures on cultural tendencies, and the mood regulation facet of the BMR Questionnaire as the DV. We conducted exploratory data analyses with two separate machine learning techniques: the Lasso regression and gradient boosting methods. Both approaches yielded similar results in identifying holistic thinking styles as strongly associated with mood regulation in music (b = 1.63, p < 0.001). Study 2 (N = 91) was then conducted to test if Holism (vs. Analysis) (IV) would be associated with the affect regulation subscales of the Adaptive Functions of Music Listening Scale (Stress, Anger, and Anxiety Regulation subscales). However, these hypotheses were not supported. Instead, the Rumination subscale was significantly and negatively associated with Holism (vs. Analysis) (b = -0.2, p = 0.005), suggesting that holistic thinkers seldom ruminate on negative emotions in music. As holistic thinkers prefer neutral (over positive) affective states, our results reveal similar tendencies in their music habits.