Prior to the 1980s it was uncommon for marketers to incorporate pre-existing popular music into television commercials. But following the rise of MTV as an innovative commercial endeavor and Pepsi-Cola’s groundbreaking 1984 “Choice of a New Generation” campaign featuring Michael Jackson, musicians and corporations began to realize the benefits of incorporating new songs into commercials. Once considered taboo by many musicians and fans, television commercials have now become such a lucrative medium for the dissemination of new popular music that by the second decade of the twenty-first century, performing songs in them has become commonplace. Despite the fact that discussions about the use of popular music in commercial culture have proliferated among music critics and trade press publications for three decades, music scholars largely continue to overlook this phenomenon. This dissertation contributes to the small amount of academic literature available on this topic and engages with recent publications by ethno/musicologist Timothy D. Taylor and sociologist Bethany Klein that warn that the convergence of popular music and corporate brands will have detrimental consequences for future of cultural production and reception. I hypothesize that what Taylor has termed as advertising’s “conquest of culture” is a result of the industry’s attempt at appropriating and reforming musical texts by manipulating their structures and signifiers in commercials to change their meanings and serve branding imperatives. This dissertation focuses on Pepsi’s attempts to inscribe itself into music history, using its 2011-12 X Factor commercials as bookends for historicizing the corporation’s pioneering transition from jingles to the use of new popular music in its 1980s television commercials. More specifically, the project analyzes the aesthetic effects of rearranging songs to fit branded environments, examining how advertising forges new contexts for familiar songs by focusing on 1980s spots that borrow MTV tropes and “re-present” musical and visual signifiers from the biggest pop stars of the day, Michael Jackson and Madonna. I integrate interdisciplinary methodologies that combine formal musical analyses, historical research, archival work, and ethnographic interviews. This dissertation draws from musicological studies on musical meaning and cultural and social theories about popular culture, music, advertising, and media.