In two experiments, we provided support for the hypothesis that stimuli with preexisting memory representations (e.g., famous faces) are easier to associate to their encoding context than are stimuli that lack long-term memory representations (e.g., unknown faces). Subjects viewed faces superimposed on different backgrounds (e.g., the Eiffel Tower). Face recognition on a surprise memory test was better when the encoding background was reinstated than when it was swapped with a different background; however, the reinstatement advantage was modulated by how many faces had been seen with a given background, and reinstatement did not improve recognition for unknown faces. The follow-up experiment added a drug intervention that inhibited the ability to form new associations. Context reinstatement did not improve recognition for famous or unknown faces under the influence of the drug. The results suggest that it is easier to associate context to faces that have a preexisting long-term memory representation than to faces that do not.