A method and system for integrating media of past gameplay into overlays is disclosed. A plurality of trigger points associated with one or more interactive content titles is stored. Each trigger point is associated with a plurality of possible results of an activity in a respective interactive content title. Each of the possible results associated with one or more media files depicting the associated result of the activity. Gameplay data sent over a communication network of a current activity is monitored. The monitored gameplay data that indicates a possible result associated with the current activity is identified. The stored media files is filtered based on the identified result of the identified trigger point associated with the current activity. An overlay display of at least one of the filtered media files is generated and provided to the client device for presentation in association with the current gameplay session.