Any Idea how you would go about syncing this up

It seems like two techniques are at work here...

One, those analogue (aka FILM) SLR cameras are shooting approximately as fast as they can, so being aware how many shot per second your camera can take is important.

Two, making the stills start on the correct moment of speech in the song.

My recommendation, if to mimic these results, would be to simultaneously shoot the stills of the talent preforming and also roll video on the talent with a mic hooked up specifically for the camera shutter and then using the video as reference for the stills later on.

And then, pay the editor overtime :)

I don't know how they did it, but thats how I would do it...
 
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Couldn't you get that effect shooting with a high shutter speed and a slow frame rate. No motion blur and you would get the chop effect you were looking for. Seems a lot easier than editing stills.
 
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