Another victim of the dreaded Pothole of Periocity. He knew the later stuff, didn't like it and never worked backward. The ease and access of music on the internet has eased the syndrome less than you might think.
Coltrane and Miles are probably the two most well-known examples of musicians who shed audience as they move through different periods. Some only go with Trane through his Prestige period, some through Atlantic, some through early Impulse and a few all the way through to the end.
How often do people who hook into Trane at Meditations go back to Blue Trane? Or, who pick up Miles at Tutu and go back to Embraceable You?
Donald Byrd (b.12/9/32) is another who made extreme enough changes that he exchanged much of his old audience for a new one. In this case, a larger one-and here the bugaboo of "selling out" rears its endless head (No comment).
Interestingly, Byrd's music became more "pop" and "soul" oriented while he pursued advanced academic degrees: Masters in Music from Manhattan, Law degree from Columbia, Phd from Columbia University Teachers College in 1982. Here are examples of the change:
Straight ahead, 1958:
Gotta say, it's early Byrd for me.
Who have you shed all along the way? Or picked up?