Methods and system for displaying a click-to-buy overlay for an item on a video in a video hosting site. The item is matched to the video according to video metadata and/or rules selected by the video rights holder. If the uploader is not the video rights holder, the video rights holder can choose to monetize the video by selecting Click-to-Buy metadata and/or rules. A viewer of the video can choose between multiple retailers for an item offered in the overlay. The viewer can further navigate between multiple overlays associated with the video while the video is playing.