Well, now that you mention it I may as well say that the problem here is thee notion of the playlist. Dylan should be enjoyed by the album, not some random selection. Blood on the Tracks, Desire, Highway 61, Bringing it all Back Home and most important of all, The Freewheeling Bob Dylan.
Playlists can go whistle. Obviously its fine to skip Lily, Rosemary and the JAck of Hearts.
It is a bit, yes. It was bad enough when CDs arrived and destroyed the notion of a song closing side 1 and opening side 2. Now you have people letting a piece of software choose random songs from an artist. It is obviously worse with someone like Dylan's who has a huge back catalogue but the principle itself is concerning.
Imagine leaping from Highway Patrolman to Glory Days. It is just several kinds of wrong.
Well that is a live show and therefore totally different. One expects an artist to create a set list that makes sense and creates an atmosphere. One also expects them to create versions of the songs that work in the set list.
Either way, it is the artist dictating the selection, not a machine.