I suspect that everyone who writes and fancies themselves to be a lethargic intellectual is at some time driven to applaud or criticize Bob Dylan, mostly because he writes and fancies himself to be a lethargic intellectual, and he manages to make a living with it. The rest of us split our days either mustering ourselves to a respectable job (because we are actually lethargic intellectuals) or slinking awkwardly from it in a way that shows we are mostly math teacher and not very much lethargic intellectual. At the end of the day, it is very difficult to distinguish a brooding genius from a sulking nerd.
Anyway, here is mine. Bob Dylan had a lot of really lousy music, and his writing was almost as bad as his voice at times. However, those 465ish songs listed at http://www.bobdylan.com/songs/index.html (some were not written by him and others were re-released habitually) are peppered with brilliance, and being the sunshiny optimist that I am, I will focus on those. Why? Because it is my blog, and having a blog is all about subjecting people to your literary whims, even if they are only echos of lame observations forty years old. This list only involves a few different albums, and it omits a handful of songs which are more obviously worth a listen.
A few Bob Dylan songs that might be better than what you are listening to right now:
Shelter From the Storm. The first time one listens to it, it seems to contain a beautiful or tragic story of some sort, and that's about as far as it gets. The unfinished thoughts and hazy imagery epitomize the poetic ambiguity that was Bob Dylan. A better Bob Dylan fan than myself would know which woman was being discussed and who the one-eyed undertaker is and all that. A better art appreciator than myself would tell me that the song is about someone or something in my own life and that I am really Bob Dylan. That's deep. But it's a great song. Do I understand your question, man, is it hopeless and forlorn?
Lily, Rosemary, and the Jack of Hearts. This is a ballad like a Sherlock Holmes story. I think that it would make a smashing music video with rustling silks and curling smoke and subtle distrust in eyes. But his bodyguards and silver cane were no match for the Jack of Hearts.
Black Diamond Bay. This song is a snapshot of drama cut short, evoking National Geographic images of fear itself entombed in Pompeii. In a few short verses, Dylan efficiently and ruthlessly developes a handful of tragic characters.
Her passport shows a face
From another time and place
She looks nothin' like that
Romance in Durango. This one is cheesy, but I like it.
No llores, mi querida
Dios nos vigila
Desolation Row. If you are a confused college student, this one makes you feel like you really understand life, but then you may realize that profundity and incoherence are not the same thing. Or you may not.
Now you would not think to look at him
But he was famous long ago
For playing the electric violin
On Desolation Row
Idiot Wind, Sad Eyed Lady of the Lowlands, Standing in the Doorway, Boots of Spanish Leather.
So go to it.