For some reason I've always been intrigued by questions about perception, objectivity and subjectivity in music; the reasons why different people like or dislike – or think they like or dislike – different kinds of music; and the various snobberies and inverted snobberies that come into play. I've touched on this in previous WILTs, but here I am this month just trying to write a few lines about two very different records I've been enjoying, only to find the theme crashing in, like a rabidly determined and somewhat scary fan who just has to get backstage.

HANK WILLIAMS: 40 Greatest Hits

I never thought I liked Country music much. Given the right time and place, though, I've found I can enjoy pretty much anything – especially Live. I enjoyed seeing Johnny Cash and Ernest Tubb (though they were both on their last legs at the time) and I had a great night a few years ago at Tootsie's Orchid Lounge in Nashville, drinking Dixie beer and Wild Turkey bourbon and watching a no-big-deal local band with a red-hot guitarist, whose name I never found out, but who reminded me that some of these guys can really play, and that Nashville ain't called Music City USA for nothin'. And how any human being can conjure such pretty sounds from a Martian torture device like a pedal steel guitar, will be forever beyond my comprehension.

The first thing that appealed to me about this compilation was the sheer nerve of its title. Forty Greatest Hits? How many people even have one hit? Yet here, apparently, was a guy with hundreds or thousands, which someone has, for my benefit, painstakingly whittled down to a mere forty of the most essential. Phew! Thanks, mate!

The amazing thing, though, is that almost every track is either familiar, or great, or both. The tunes are catchy as hell and the lyrics are sometimes funny, but quite often heartbreaking. Everything there is to say about Hank Williams has probably been said already. All I can do is point out what particularly touches me, which is the depth of feeling he's able to bring to songs which are sometimes about as simple as a song can be, and still hold together as something like a song. Most of them, for instance, have only three or four major (hardly ever minor) chords. It should all sound happy in a dopey, naïve sort of way, but it's often drenched in melancholy, and a world-weariness that's scary coming from someone who died so young. (I just checked to see if he's a member of the infamous '27 Club'; in fact he was 29).

If I had to pick a favourite, it might just be Ramblin' Man, the only song I'm aware of that Williams ever wrote in a minor key. That is, it consists (in musicological terms) of a slowly strummed A minor chord, occasionally changing to E major and then back to A minor again, with a melody that just runs up and down a few notes of an A minor scale. That's about it. But the vocal, and the atmosphere, the vibe, captured in the recording, are spine-chilling.

THE OSCAR PETERSON TRIO: Night Train

I never thought I liked Oscar Peterson much, either. I remember seeing him on TV many, many years ago and thinking he had incredible technique and showed off a lot, and, what's more, did it with a big smile on his face like it was all too easy. Maybe I was just jealous. It didn't seem so easy to me!

Or maybe, like many people, I was flirting with the romantic idea that an artist with obviously extraordinary technique must somehow be less 'authentic' than a more 'primitive' one who, of course, has lots of 'feel' or 'soul' (like Hank Williams, maybe). Though at least I don't think I ever fell into another common trap, that of feeling personally affronted, and becoming defensively scornful, when confronted with music I don't really understand.

Kurt Vonnegut neatly satirized all this sort of thing in a famous short story, Harrison Bergeron, set in an obsessively egalitarian future society whose leaders – for the greater good! – devise ways to handicap anyone with too obvious a talent. Beautiful ballerinas, for instance, have to dance wearing masks and with weights attached to their bodies, so that the clumsy slobs in the audience won't feel 'lesser' than them.

Vonnegut makes the story even more provocative with a twist: when the prodigiously smart, handsome and talented title character breaks free of his restraints, he declares himself Emperor, and promises anyone who follows him that he'll make them barons and earls. He is then shot dead. Whole cans of aesthetic, political and philosophical worms are opened here in just a few pages, but among other things I'm reminded of a comment by another fascinating author, Robertson Davies: that it's silly to talk about Art being democratic when it is inherently aristocratic. We can certainly try to democratise peoples' access to it, or the education needed to appreciate it. But there will always be good and bad artists, as well as a whole lot of so-so ones and a handful of geniuses.

Back to Oscar Peterson: many years after dismissing his artistry, I'm listening to a Brazilian-Jazz compilation, and at the end of one track an obviously brilliant pianist starts improvising beautifully on the intricate chords of one of Jobim's lesser-known bossa novas. He's playing mostly in eighth-notes, but on the next chorus, he doubles the time, and starts to improvise just as fluently and imaginatively in 16th notes. Then the key moves up a half-step, and he just keeps going, relentlessly confident. And on he goes into the next chorus, when, as the key shifts up another half-step, he adds the left hand and improvises in octaves. By this time my eyebrows are practically touching the ceiling. Again the key moves up a half-step and on he goes until the track fades out, and even the fade-out seems to make a statement: yes, I can keep this up this all night. No prizes for guessing it turned out to be Oscar Peterson.

Some years later, in a secondhand record store, I pick up a 1957 Verve album which teams two tenor sax legends, Coleman Hawkins Encounters Ben Webster. The first track has a couple of beautiful, soulful, funky, blues piano choruses before the saxophones enter. I like it so much I reach for the credits to see who the pianist is. Oscar bloody Peterson.

Nowadays he's on the never-quite-finished list of my favourite pianists that I was toying with last month. Night Train is the Peterson album I'd recommend first. (The title track, incidentally, was originally written as Happy-Go-Lucky Local by Duke Ellington, and much later transformed into the better-known Night Train by James Brown. Peterson's version lies right in between). There's not a dud track on this album, which is one of the all-time piano trio classics, with the great, great Ray Brown on bass, and on drums, Ed Thigpen, about whom I have two questions: (a) how does a drummer sound so good, and swing so righteously, while playing soft enough to stay out of the way of two acoustic instruments? And (b) what was his nickname at school?

Anyway. What I think is: there's no inherent moral superiority in being a highly skilled and trained musician, or a raw, self-taught, illiterate one. Cleverness can be sterile, or it can be inspiring and fun. Simplicity can be heartfelt and moving, or as dull as dishwater. The only hard-and-fast rule, though, is probably that there are no rules.