Power ballads and their media adaptations – whether as standalone music videos or as part of film soundtracks – are an integral part of Western popular culture in the 1980s and 1990s. From this perspective, power ballads can be understood as multimedia entities that create new meanings with every media adaptation. In this article, I will analyze the song “How Am I Supposed to Live Without You” by Michael Bolton, focusing on the lyrics and the musical form, as well as the studio recording and the music video. I will demonstrate that the song and its adaptation across different media, as well a within in a specific genre context, give rise to varying meanings that are of crucial importance to Bolton’s development as an artist and as a star.