In this paper, I examine Strauss’s critique of Collingwood’s interpretive approach and argue that Strauss’s accusation of historicism partly misses its target. While Collingwood can be said to be a “historicist” thinker insofar as he pursues the project of the German historicist tradition and attempts to establish the autonomy and specificity of philosophy of history as a discipline, he does not endorse the premises of radical historicism according to which all thought is historically relative. Although many of Strauss’s arguments against interpretive historicism are valid, they do not apply to Collingwood’s enterprise. In creating a dialogue between the two thinkers, I demonstrate that their respective theories of interpretation are as a matter of fact closer than they appear at first sight. Both philosophers defend the possibility of understanding past authors as they understood themselves, they maintain the importance of the quest for philosophical truth in interpreting the past texts and make the case for the necessity of history for philosophy.