How do I link gallery images to custom popups?

PopUp Pro is a dream come true for me. I needed somthing to create popup pages that were each customized. Creating the content is a breeze. Now, how can I create an image gallery and point each image to the customized popup? I'm using Headway Themes and there are any number of gallery options. Perhaps the WP gallery would work as well? I've attached an image of what I want to do. My site will feature performers and, when you click on the image in the gallery, it will popup with information about that performer. Thanks!