A detailed interpretation is provided of the ‘Gray's Elegy’ passage in Russell's ‘On Denoting’. The passage is suffciently obscure that its principal lessons have been independently rediscovered. Russell attempts to demonstrate that the thesis that definite descriptions are singular terms is untenable. The thesis demands a distinction be drawn between content and designation, but the attempt to form a proposition directly about the content (as by using an appropriate form of quotation) inevitably results in a proposition about the thing designated instead of the content expressed. In light of this collapse, argues Russell, the thesis that definite descriptions are singular terms must accept that all propositions about a description's content represent it by means of a higher-level descriptive content, so that knowledge of a description's content is always ‘by description’, not ‘by acquaintance’. This, according to Russell, renders our cognitive grip on definite descriptions inexplicable. Separate responses on behalf of Fregeans and Millians are offered.