Don't really agree with your thesis about songwriters. Many have written their best songs early in their careers. In fact every major songwriter I'm a fan of has disimproved with age. McCartney, Paul Simon, Paul Weller(drastically) even probably my favourite, Elvis Costello. I'm not a Bob Dylan fan by any means (can't stand the voice) but you raised the lyrics of "The Times......." If my memory is right it begins:
"Come gather round people wherever you roam and admit that the waters around you have grown, and accept it that soon you'll be drenched to the bone, If your time to you is worth saving, then you'd better start swimming, or sink like a stone, for the times they are a changing"
Not too shabby lyrics there I think you'll agree. OK they're pretty literal, but also literate.
On to Billy Bragg. Again some of his early songs are some of his best. (I quite like the Milkman of Human Kindness line you quoted btwdon't think it's embarrassing at all.) Take "A New England" or the majestic "Saturday Boy"
"She danced with me and I still hold that memory soft and sweet
And I stare up at her window, as I walk down her street
But I never made the first team, I just made the first team laugh
And she never came to the phone, she was always in the bath
I never understood my failings then, and I hide my humble hopes now
Thinking back, she made us want her
A girl not old enough to shave her legs"
Anyway, I'm kinda sorry I got a bit sidetracked into the whole lyrics thing, which is a mistake a lot of people make when discussing songwriting in my view. The tune is just as important, in fact more so I think. Otherwise it might as well all be poetry. One of my favourite bands is Teenage Fanclub, and their lyrics are no great shakes really. I do think Damien Dempseys lyrics are pretty rubbish, but I could forgive that. It's the absence of decent tunes
and what is (to my ears anyway) an awful voice that puts me off. I'll freely admit I haven't heard much of him, but I have heard a couple of the songs mentioned above - Spraypaint Backalley, Negative Vibes, It's All Good are the ones that come to mind.
In the end of course, it's as you said. You either like him, or you don't. But I've enjoyed the debate.
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