The trouble with painting/drawing portraits is everyone gravitates to the question whether it looks like the person it's supposed to be. That's a good reason — if you like doing portraits — to choose subjects who aren't well-known. Alternatively, use a camera. You might get credit for making one person look like someone else.
Here's Bob Dylan's new "Self Portrait (1969-1971): The Bootleg Series Vol. 10." And here's Dylan's long-ago release titled "Self Portrait"...
... the one about which Greil Marcus asked in Rolling Stone: "What is this shit?" (Here, please credit me for resisting making a Santorum joke.)
Comparing the 2 selfies, we see a consistent approach to the upper lip/lower lip proportion, the the Scarecrow-from-the-Wizard-of-Oz nose, the hair part deeply denting the forehead (making it look like a lopsided heart), the cut off jawline with jowls, and the un-level ears (though the down ear is now up and the up is down*). The biggest difference, other than skin tone, is in the eyebrows. Gone is the amazement of youth. The old man has seen it all, but he's still looking.
_________________________
*Old lyric that resonated (after a search for "up" and "down"):
Oh, the only decent thing I did when I worked as a postal clerk
Was to haul your picture down off the wall near the cage where I used to work
Was I a fool or not to try to protect your identity?
You looked a little burned out, my friend, I thought it might be up to me
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