I have only just realized that the country song “The Highwayman” was originally written by Jimmy Webb. I listened to his version recently, and it does seem to drive home the reincarnation message more clearly by having all the lives sung by the same person.
Of course there also seem to be other themes highlighted by The Highwaymen’s cover having all the lives sung by different people. Since all of the lives are people working dangerous but rather romanticized jobs, it also seems like it is more generally spirit of the working man.
I’ve always enjoyed the song and its themes, as I always really enjoy those sorts of romantic folklore tales.