This thesis explores the divergent legacies of two trumpet titans of the 20th century: Louis Armstrong and Harry James. Both emerged during the swing era as technical virtuosos and cultural icons, yet Armstrong remains a household name while James has faded from mainstream recognition. Through detailed biographical and historical analysis, this study argues that Armstrong’s enduring legacy stems not only from his musical innovation but also from his remarkable adaptability across changing media, audience tastes, and cultural moments. By contrast, James maintained a more rigid artistic identity, achieving enormous success during his peak but failing to evolve with post-war musical trends. The thesis situates both artists within the broader shifts of American music, media, and race relations, demonstrating how cultural longevity is shaped not just by talent but by strategic reinvention and cultural relevance. In doing so, it offers insight into how memory, identity, and entertainment intersect in American musical history
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