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Research that interrogates the intersections of art and commerce finds that artists rely on social connectedness as a strategy for mitigating career uncertainty. How though do individual artists orient themselves toward art or commerce when collaborating? Songwriting is highly collaborative among professional songwriters, but during the industry decline in the 2000s, songwriters increasingly had to collaborate with recording artists. I analyze interviews with 38 hit songwriters to examine responses to this form of inter-occupational collaboration. Songwriters responded by developing two strategies. First, a process of bespoke facilitation that shapes songs toward the recording artist’s persona—commercial orientation. Second, a strategy of pre-writing songs and insinuating that it was a product of the collaboration—an orientation toward artistry. Both are deceptive to the recording artist but effectively orient the songwriter toward either art or commerce while maintaining collegiality and promoting future collaborations.