This article makes visible the complex social position of a previously overlooked class of Southern Song artists: freelance painters, who worked for the imperial court on a temporary, as-needed basis, but who have been mischaracterized as permanent, official “court painters” by post-Song historiographers. Through an analysis of the careers of freelance painters such as Chen Qingbo and Li Dong, I posit a hybrid class of adjunct-artists, who made their livings by operating fan shops in the capital's streets but at times also contracted with the court. How did the emperor exploit contingent artists while simultaneously allowing market agents (guilds and brokers) to protect their benefits? How did the freelance painters increase their profits by developing entrepreneurial relations with the court and by competing with other freelancers in a fierce market? By exploring how the Southern Song court mobilized non-court painters through consensual contracts, this article differentiates freelancers from court painters, thereby dismantling long-held myths about the Southern Song painting academy.