The literature on populism used to depict the phenomenon as an alternative to the standard path from traditional to modern society; as a way to enfranchise the underclass; or as an anomaly vis-à-vis class politics and liberal institutions. More recently, the debate has shifted into something of a terra incognita as a result of the growing interest in the connection between populism and democratic politics. One of the more intriguing contributions to this debate is an article by Margaret Canovan, if only because it makes this unknown territory less confusing. Her argument draws from Michael Oakeshott's claim that political modernity is characterised by the interplay of two distinct styles – the politics of faith and the politics of scepticism. She renames them the redemptive and pragmatic faces of democracy and suggests that populism arises in the gap between them. This establishes a relation of interiority between populism and democracy. The former will follow democracy like a shadow. At times, however, the theoretical status of the gap is somewhat uncertain, as it seems more appropriate for thinking politics (particularly radical politics) in general. The political valence of the shadow could also be specified further to show the undecidability between the democratic aspect of the phenomenon and its possible ominous tones. This paper looks into this in some detail to engage in a friendly interrogation of Canovan's claims.