Here’s some traits that I’ve learned from interviews with various people who have known him, although his behavior has definitely changed over decades… There have been times when drug use has certainly affected his personality, particularly the mid-60s when he was on speed.
Clearly he is an oddball - a very eccentric and reserved person who despises attention rather than seeks it. Many believe that he might have Asperger syndrome because he is so noticeably aloof and detached. Dylan’s generally not very talkative or open. He also has a somewhat strange way of speaking, and I don’t just mean using short concise sentences. Larry Charles said in a radio interview that when he was having a cup of coffee with the musician, Dylan ordered a “Hot beverage”. Charles ordered an ice coffee and Dylan started drinking his beverage instead. This was in the late 1990s. I think he enjoys playing with people like that, testing them in a way.
As far as I know, he became more quiet and introverted once he quit boozing in 1994 or so. Overall he doesn’t say much and isn’t very approachable to begin with. Might be that he has trust issues, which is understandable. Not that he cannot ever be friendly, but he doesn’t want to take pictures with fans the way most other musicians do or have a chat with them, and I’ve heard his personal security guards aren’t even allowed to look him in the eye.
Apparently it’s easier to get into a conversation with him if you don’t treat him as a celebrity or a great talent, he prefers to be thought of as a regular person. You can talk about cars or books with him but once you bring up his music, he just shuts down. He especially doesn’t like to be asked about the meanings of his songs. When Dylan became a student of Norman Raeben, an artist, he very much enjoyed the fact that Raeben didn’t have a clue that Dylan was a famous musician. Larry Charles has also said that when people ask dumb things like “Why did you go electric?”, Dylan’s typical answer would be something like: “I dunno, why did you go electric?”. Or he can literally just walk away and create awkward situations but he somehow doesn’t feel awkward about it. That’s how he just is.
The impression I’ve gotten from different books (by Joan Baez or Victor Maymudes, for example) is that he can have a quiet and relaxed demeanor yet sometimes act like a vicious bully. It seems that he can get triggered very easily or get pissed about things like his personal items or money. Marianne Faithfull has shared a story about Dylan becoming completely furious when she rejected his advances once, but perhaps he was just high. I don’t think Dylan is very empathetic and can easily hurt people without necessarily wanting to hurt them. He often becomes an unintentional jerk and even uses people. I doubt that he acts like a dick on purpose, he probably treats others the same way he often gets treated by insincere people. It might sometimes be an effective way to get people to leave him alone if he just wants to be alone. That’s how he simply protects himself.
He has many strange quirks. There are numerous stories about his bad hygiene etc. Joni Mitchell had a traumatic experience when she happened to smell Dylan’s breath.
Through the years, I’ve read what seems like hundreds of stories about Dylan and I really haven’t seen anyone speak super highly of him. Of course everyone thinks he is a brilliant artist and rightfully so, but as far as his personality goes, there are not too many impressive stories. No one really calls him an amazingly humble or kind person. He just has that serious, cold attitude that can be alarming. At the same time, he has a strange charm - women are absolutely drawn to him even if he hasn’t washed his hair for a week. I believe there is a very caring and warm person deep inside of him, but he likes to act indifferent and annoyed so that everyone around him wouldn’t try to become pals with him.
Having said all that, as a father and husband he is definitely just a normal dude as long as he’s dedicated to enjoying a peaceful life and not touring, which is what he did for years after his motorcycle crash. We all might think of him as this mystical figure, but at the end of the day, he changes his kids’ diapers, reads them books and goes to sleep with his wife like everyone else. In fact when A. J. Weberman, a Dylan obsessive, was going through Dylan’s trash, he mostly found shitty diapers.
I think this is an excellent interview where Dylan doesn’t have his guard up (so to speak) and is quite open and willing to talk honestly without acting like a quiet ass. While he’s answering questions, he’s even sketching the interviewer:
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