This paper examines Hume's comments on and claims about ancient philosophy. A clear and consistent picture emerges from doing so. While Hume is a lover of ancient literature, he holds ancient philosophy in very low regard, as passage after passage discloses, with one qualification and one important exception. Hume appropriates the mantle of 'Academic' sceptic for himself; but in fact his Academic (or 'mitigated') scepticism has only minimal affinity with the ancient school of this name, having more in common with early modern sceptical positions. The exception is found in the 'painterly' depictions of character and other features of moral life, where Hume holds many of the ancients in very high regard, seeing them as superior to the moderns. The bases of these respective views of Hume's are explored, with an interpretation which construes Hume's 'anatomist'/'painter' contrast as meant non-ironically. On the anatomist or theoretical side, Hume nonetheless - rightly or wrongly, and contrary to the views of a number of his prominent readers - sees a radical, dramatic break between early modern 'scientific' philosophy, and anything which preceded it.