The key element here would be to get students playing early on and reading/watching/viewing/listening to lots of things with this lens turned on. This may even be a decent reason to use Prezi as an authoring tool to get at mixed media embedding and connecting with text and the benefit of zoom levels.
Two possible options follow . . .
Option one is to link the works through common literary allusions. For example, the myth of Icarus could be used to tie a variety of disparate1 works together. This becomes a more interesting English assignment as you compare the ways in which the allusion is used by the various authors/artists.
With Icarus as the central theme, I might connect the following.
The Letting Go – One of the stories from The Moth2 about an oncologist dealing with death in America submitted under the theme Too Close to the Sun. Here I should get points for audio, modern, and either philosophy or science.
There are some interesting arguments about the Led Zepplin/Swan Song logo (modeled after the Rimmer painting) and whether it represents Icarus or not.
The Icarus Project also tempts me in a variety of ways.
Option two, would be to chain allusions in a circle. So you’d start with a work that has Icarus as an allusion and tie it to a work with an Icarus allusion and one other allusion (let’s say Midas for this example). Midas would then tie you to your next work and so on and so forth until your 6th piece links you back to Icarus.