In recent years, numerous marketing and organizational theorists have called attention to the analogy between jazz and management strategy. From the perspective of this jazz metaphor, key questions concern the implications of jazz training for marketing education. Too often—say, in motion pictures or television dramas—jazz is portrayed as an innocent folk music whose performance requires more feeling than knowledge. This inaccurate stereotype colors the treatment of music instruction found in the film Mr. Holland’s Opus (1995). A contrasting view of jazz as a technically demanding art form appears in the movie Whiplash (2014). These two films also represent diametrically opposed teaching styles—the first nurturing and customer-oriented, the second sadistic and product-oriented. A third motion picture entitled Keep On Keepin’ On (2014) presents a resolution of this dialectic in the form of a marketing-oriented instructor whose method of teaching combines kindness (the customer-oriented thesis) with rigor (the product-oriented antithesis) to achieve a balanced reconciliation (the marketing-oriented synthesis). From this perspective, like jazz training, marketing education is itself embarked on a marketing project that benefits from a rapprochement of customer-oriented and product-oriented impulses to attain a marketing-oriented synthesis. Thus, insights about jazz training become relevant to the challenges of marketing education—as illustrated by various examples from the author’s own experiences.