This kind of reminds me of a group I love listening to: Postmodern Jukebox. Instead of syncing modern music to old-time dance videos, they take modern music and envision what it would sound like if other singers sung it.

For example, here's Ex's and Oh's as if it were a Jazz song: https://www.youtube.com/watch?v=SQ2N_VurqAk&list=PL7A4D9C100657150E&index=38