A context based tag recommendation system for annotating stock photography media files, the system configured to: maintain a first database comprising a set of media files and a set of annotations associated with the media file set, maintain a second database comprising a second set of records, each record comprising an annotation, at least one co-occurring annotation, and a count, receive at least one media file tag input (input), query the second database using the input to identify a ranked set of co-occurring annotations and a count associated with each annotation in the ranked set of co-occurring annotations, query the first database to identify a selected set of similar media files, by iteratively retrieving image files associated a selective group of annotations from the ranked set of co-occurring annotations, present a list of recommended annotations based on the ranked set of co-occurring annotations and the selected set of similar media files.