Entertainment is the “killer application” for high value telematics services in vehicles. Entertainment does not require a new, untested consumer business model: consumers have been “paying” for entertainment in vehicles for decades. Examples include purchases of audio cassettes and CDs; listening to radio advertising; and more recently, the rental or purchase and playback of videotape movies in the rear seat. Today, technology advances in digital satellite broadcasting, digital compression, mass data storage, and broadband wireless communications are driving very dynamic business opportunities for entertainment service delivery to vehicles. Obvious examples are XM and Sirius Radio, DVD movies, rear seat video games, and MP3 audio playback from flash memory or hard disc drives. A more advanced example is the direct sale and download of compressed digital audio, video, and game software via wireless links that bypass the conventional bricks and mortar retail business. This paper explores the potential timing and business opportunities related to these technology driven services.