There are 20 tracks on the left, each one seems to be compatible with 5 - 10 of the ones on the right. There would have to be 100-200 pre-made mashups covering all the combinations, so there must be some sort of systematic method for mashing up.
Oh; no there isn't [1]:
> Just cranked through em all for two weeks. Thought about automating it but it wouldn't sound as good
"When in doubt, use brute force", i guess. That said [2]:
> They're templatized, so phase 2 is to do it programmatically. Everything up right now was manual though :)
When I read mid-2000s themed mashup my first thought was how 10 years ago there were a lot of startups that just took two apps and made them work together (like Google Maps + Flickr).
It would be cool to drag and drop to make those kind of mashups.