For some time, The Athenaeum has allowed users editing a person to “connect to an image of” that person. This means that you can look up an artwork that depicts a person and make the connection, creating a link from the artwork page back to the person portrayed. It also allows the person detail page to display a random (known) portrait each time you load the page. The search interface to make the connection is a bit clunky, but it all works well once it’s set up.
Recently we spent some time adding a number of these links on the back end through database queries. In particular, we set up several hundred links for self portraits. Once we had those, it wasn’t hard to add a section on an artist’s page to display any known self portraits. To get an idea of what this looks like, check out the page for Vincent Van Gogh.
This all only works as well as the data itself, so if you see a portrait that has not been connected to the person, why not link them?