It seems to be recent, on the one hand, but Dylan looks quite a bit younger than he does now so I can't figure out when it was recorded.
To belabor my point about his singing, take
this song. The refrain of "you left me standing in the doorway crying" is sung several times to the same tune, yet as the song develops Dylan's intonation and phrasing continually evolve to fit different underlying emotions. At first he says it with resignation, almost wistful, perhaps with self pity, but later on it turns into indignation or anger or astonishment and other shades of emotion that are hard to specify. It's a person saying important stuff with appropriate emotion as well as a singer staying within the confines of the melody.