Bob Dylan was born Robert Zimmerman in Duluth in May of 1941. He is a Gemini.
Moon in Taurus
Mercury in Gemini
Venus in Gemini
Mars in Pisces
Jupiter in Taurus
Saturn in Taurus
Uranus in Taurus
Neptune in Virgo
This is an example of what is called the final depositer in a chart.
Mercury is at home in Gemini, in the sign that Mercury rules and is Mr. Dylan's final depositer.
Right away you can see that he has no planets in fire signs and only one in a water sign, his Mars in Pisces. He would deal with life through his mental abilities and his heart and emotions would be extremely stable in the earth sign of Taurus.
It is easy to find a final depositer in a chart because it will always be the planet in the sign that the planet rules, if your chart has one.
Mercury is the planet of communication and it is Mercury that is the key planet in understanding Bob Dylan.
Sometimes a planet will "run away" with a chart because it is conjunct a fixed star. Sometimes a planet does this by being the only planet in an element such as Mars being the only planet in an water sign.
Career is often indicated by what planet trines (120 degrees) the midheaven. Dylan's Venus trines his midheaven which leads one to think of an artistic career. His Moon is in the 5th house of creativity. The Moon is said to show where our heart is and Mr. Dylan probably enjoyed his career.
I think it was something that I would expect that his final depositer would be Mercury.