David Hepworth once wrote that if you're under 50, you probably don't get Bob Dylan. I think his point was that the way Dylan approached music making was more influential - on both musicians and listeners - than the music itself. If you are old enough to have been influenced directly, then you are more likely to appreciate it. On the other hand, a younger person will - can - only judge him by his musical legacy.
I think this is very plausible and goes some way to explaining why I've always considered Dylan to be really overrated. For me, the music does not stand up by itself. I've never been interested in lyrics, particularly any that are cryptic or pretentious. It's supposed to be pop music, not pop poetry (and yes, Bob Dylan is pop). Musically, Dylan can be really tiresome: his voice is an acquired taste at best (infernally grating at worst), the harmonica playing is horrible and most of the instrumentation sounds like an afterthought.
The more I learn about Dylan, the less I like. He is such a fake. The whole persona is a construction. The protest singer who made his name in New York isn't any more genuine than the folk rock revolutionary of the mid-sixties or the hillbilly from Nashville Skyline. Not that this should matter at all: I rather like Nashville Skyline, as it happens, because it has good tunes and decent musicians; and Bowie made his career out of alternative identities. What rankles is that at no point does Dylan admit that it is a construct. Sure, the mystique clearly works for him. It just annoys me.
Anyway, this is his second album. The best songs have a proper tune, even if Dylan's voice is only barely
up to carrying it: "Masters Of War", "A Hard Rain's A-Gonna Fall" and
"Don't Think Twice, It's All Right" (I think it's significant that,
uniquely, covers of Bob Dylan songs tend to be better than the
originals.) However, too much is affected, "rootsy" folk: "Bob Dylan's Blues", "Down The Highway" and "Talkin' World War III Blues" are all rambling tedium over rudimentary backing. It's probably good of its type but it's not enjoyable music.
Despite all this, I like Freewheelin'. I only bought it this year but I've known it since I was sixteen or seventeen, when my friend Josh got a copy on second-hand vinyl. He played it to death, and listening to it now takes me straight back to those winter evenings spent smoking dope, talking pretentious bollocks and writing our own songs. Even the rubbish tracks are evocative and heavily influenced Josh's own writing and performances, which, for personal reasons, I love. It does mean that I won't listen to this album very often. Those memories are among my most precious; I don't want to risk losing the ability to summon them.