I do think that the major role music plays in certain shows makes it easier to find good matches. Otoh, I've always been slightly wary of Dean's music choices that strike me as more appropriate for someone 10 years his senior...oh, like, let's say Kripke?...than someone born in the late 70s.

Or maybe it's the discrepancy between the mood of many stories that doesn't wholly fit the tone of the show that makes the songs sometimes not work all that well for me?

and you're totally right about change of perspective and different contexts. I decided to keep the song and when listening to it again, I felt it did work for me (and hopefully will for other listeners!)