So, thoughts on Kid Rock? As a non-American, I always imagined that would be the definitive trailer trash music. For the record, I can't stand Kid Rock. I think his music is terrible and dumb, so maybe right up your alley? :p:

I actually listened to one of his albums the other day cause I thought the same thing. Meh. I like his singles for the most part, but after that he can't really keep his persona as "charming", and the songs aren't really there either. Unless I'm just not giving him enough of a chance he seems like the kind of artist who shoots his wad on a few songs and then produces steaming piles of filler.

I've only bumped into his music occasionally but there didn't exactly seem to be a lot of variety to it.

While on the topic of somewhat cheesy/"uncool" music that won't generally find an audience on MB, here's a few things I like a LOT.
I don't expect you to check it all out, nor to like any of it, but I imagine you would be the only other person on this site who could even possibly see the appeal:

Hey now, Kylie gets a lot of credit around here.

As for the OP, I used to have an issue with communicating how I feel about music to myself and others but the more I tried to fix that and practice it, it became easier to identify what it is that I don't like about a song, artist, or album. I still have a lot of room for improvement on that though. Just keep trying and if people ask you what the hell you mean by something that you said on an artist, that's an opportunity go deeper into how you really feel about the music that's being discussed. This can be a rabbithole towards argumentative close-mindedness though, so proceed with caution.

And never be afraid to sound like an idiot. If you hold back cause you're self-conscious about sounding like you don't know what you're talking about then you'll probably ignore the best bits.

I, too am largely mystified by what exactly causes me to love certain things and be utterly ambivalent toward other artists, even those which seem to have all the qualities I should like based on my other favorites. I may just be a picky curmudgeon who wants to listen to the same 30 songs over and over, though.

Kylie!
Kylie >>>> Madonna
It always irks me when people-- outside of this forum, anyway-- always credit Madonna as the most important pop (mainstream pop) innovator while ignoring people like Kylie Minogue. Though I hear she's much more appreciated outside of America.

I, too like a great deal of uncool music (I have a deep and undying fondness for failed early 2000s girl bands + bad french snythpop) but I couldn't possibly fit all of it in one post.

Madonna never really did it for me. I don't find her all that good of a singer. Especially not during her breathy, sexed-up 90's time.

Bad French synthpop is a genre I have yet to explore. I'm sure I'm missing out, big time!

Why must we choose between Kylie and Madonna? Both are ace and I would sex up in their primes.

I like different kinds of music for different reasons, but one quality that sticks out for me is what I call "color" in music. This is found most readily in certain kinds of classical music - particularly Debussy, Ravel, Satie, and the other "French impressionists" - as well as psychedelic rock.

To me, the following two pieces of music are really kinda the same. They're both extremely "visual" in a way that's hard to describe, unless you simply "get it."

I guess I get what you mean, they both give off a similar feeling through a different type of music, similar to how you can look at two horror paintings with entirely different art styles and content that still give off the same creepy vibes.