Mobile streaming is increasingly viewed as a major advancement in the wireless industry, as it enables users to consume content without any time or space restrictions. Mobile TV serves as an excellent example of streaming, providing services for watching TV content on mobile devices. While previous studies have explored video-on-demand (VOD) purchasing factors in mobile TV, it is rare to find research examining differences based on users’ mobile TV usage types, such as subscribers and free users. Consequently, we investigated VOD purchase factors for 310 subscribers and 311 free mobile TV users. In other words, using 621 survey responses, we analyze the influence of personality traits, intrinsic and extrinsic motivations, and mobile-related factors on users’ VOD purchase intentions and behavior. Our findings indicate that mobile TV utilization, hedonic needs, and subjective norms are positively related to VOD purchases, and that neuroticism, extraversion, openness, and conscientiousness positively impact mobile TV utilization. We also examine the relationships between the constructs within two sub-groups to highlight the differing perceptions and behavioral patterns of these groups regarding mobile TV utilization and VOD purchases. Theoretical and practical implications are discussed as well.