Alternate film and or music pairings

Would a modern remake of the Bullitt car chase scene or ending to the Blues Brothers go better with more modern music? What might be the sound track if Star Wars were made in a Soviet North America? Either with existing films or those in an alternate history, what different musical scores might improve the movie or would they change altogether simply by changing the timeline?
 
You're a bit hard-pressed to update the music in "The Blues Brothers" without going out of genre. You might get away with newer bluesmen, but...
 
A modern "All's Well That Ends Well" Shakespeare production that has an epilogue where the Helena/Bertram marriage falls apart. Soundtrack: "All Too Well 10 Minute Version" by Taylor Swift.
 
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