The aim of this paper is to evaluate critically competing theoretical perspectives towards off-the-books entrepreneurship, namely the modernist perspective that depicts such endeavour as a leftover from a previous mode of accumulation, the romantic perspective that depicts it as a chosen alternative to the formal economy, the survivalist perspective that views it as a by-product of contemporary capitalism and survival practice for those marginalised from the circuits of the modern economy, and the social actor perspective that views off-the-books entrepreneurship as chosen for social, redistributive, political or identity reasons. To do this, a 2005/6 survey involving face-to-face interviews with 102 off-the-books entrepreneurs in Moscow is analysed. No single theorisation is found to be universally applicable to all Muscovite off-the-books entrepreneurs. Instead, all are found to be valid in relation to different populations of off-the-books entrepreneurs, and only by combining and using them all is it asserted to be feasible to achieve a finer-grained more nuanced explanation of the complex and heterogeneous character of off-the-books entrepreneurship.