F. Scott Fitzgerald and Ernest Hemingway wrote to and about each other, from their meeting shortly after the publication of The Great Gatsby in 1925, until Hemingway’s A Moveable Feast was published posthumously in 1964. Their correspondence reveals a consistently deployed sexualized discourse in order to trope anxieties about the relationship of masculinity to commercialism and to art. The code these writers developed enabled them to negotiate shifting power relations as they vied with each other to be the better artist, and the more successful man of business. Trying to reconcile high art with commercialism, they sought to manage conflicting cultural ideologies that declared commerce masculine but vulgar, and art feminine but pure. Mixing the language of the Puritan work ethic with sexual metaphors, they measured their success against each other and their culture’s shifting definitions of value. The notorious ‘matter of measurements’ episode in A Moveable Feas only becomes fully legible when it is read within this history of competitive ‘measuring’.