Asking as a huge Bob Dylan freak, but not so much I'm not blind to the fact he's been, with rare but very notable exceptions, pretty useless for, oh, 30 years or so: did he deserve the Nobel Prize, or not? Maybe a dated question, but to me a fascinating one. I'm in the qualified 'No' camp.
I think yes. Unlike a Pulitzer which is for a single work, the Noble celebrates a lifetime. His songs, msny, especially the earliest stuff, are very poetic. All these awards are subjective; although granted with the science awards the winner needs,to have done something important, or new, and broadened knowledge. There have been awards, even in science, that in retrospect were poor choices. I think Dylan's award will stand the test of time. Possibly some one else may have been a "better" or as good as a choice. But Dylan, as you even state qualified. All subjective - not his best the last 30 years but some good stuff. Look up other literary award winners and see how many were excellent their entire lives.
I knew Bob before he became. We had played a couple of gigs in Dinkytown where he was just getting warmed up. About a year later I was one of many working the Village when he came into town. His prime motivation came from Guthrie and he emulated the Guthrie approach to writing beautifully. It didn't take long for him to move beyond that and become the innovator he is now known to have been. He quite literally took over the scene in the Village and Dylan wannabes began popping out of the woodwork everywhere with neck-strap harmonicas and deliberately styled grating voices -- but there was only one Dylan. Those of us who were purists wrote him off rather quickly when he started into the rock style folk and continued hardening. We didn't care for his music treason, but his writing was still superb.
Do I think he deserved the Nobel? Oh, hell yes. He didn't get it for his music, which I think has always been of the more-or-less variety. He got it for literature. In other words, his lyrics. His lyrics were always edgy and poignant. His voicings were constantly fresh and filled to overflowing with intense message. So, damn right he deserved the Nobel Peace Prize in Literature.
I'm a Dylan fan too and think he deserved the Nobel but, like you, I get annoyed at all of his fans that won't admit that he's been pretty lame since the early 90s. Can't sing anymore and really couldn't after the early 90s. Can't play the guitar anymore either. He ought to retire, but will probably perform until he dies, which, since he doesn't need the money and people will still come to see him, is his right.
His poetry is epic. His lyrics are the echoes of the 60s through now. He deserves to be named king of the universe.