I don't understand Miles Davis' "Kind of Blue"

Well J I think you raise a rather interesting question in general.
That is does a deeper understanding of anything make you like it better,it can but I do wonder,depends also if you like to challenge yourself,explore new things but surely at the end of the day you got to like something for what it is and enjoy it.
I remember on another mailing list I got involved in a big debate about later Stanley Kubrik movies-someone there went on to explain in great length about his genius,it was all worthy stuff and I could see his analysis had great depth but from point of view despite trying again to watch some of his later movies-I really don't like anything he did that much after Spartacus.
At the end of the day we like movies for different reasons and although I understand Kubrik's genius better it's not for me.
To get back to KOB,well as a mainly rock/popular music fan who has got into jazz a bit in the last say 5 years.
I think my namesake Sd will be much more worthy to comment on KOB but I will add some of my own.
I would suggest you listen to it a lot more before deciding.
You have to put it in context what went before and realise that Miles Davis created something new and unique with developing his modal style he'd been working on previously.
It was (I think) a very original record at the time and it's impact is such that over 40 years later people are still falling in love with it.
Of course there are many listeners who have "never got it" over the years.
The success and charm of this music to me is in it's simplicity,it is hypnotic,relaxing and at the same time strangely dynamic but that's just me,the record was some 37 years old before I heard it.
I would consider it mood maybe even ambient music in the wider sense.
Jazz can be a very difficult genre to get into,the smoother stuff can seem lightweight and the far out stuff as weird as music can get but KOB is really at the centre of the sophisticated,thoughtful side of things and maybe it's not for you.

I also am not big on Miles Davis , regardless of the popular opinion I don't find his style holds my interest. Kind of Blue was recorded in one take which is what is supposed to make it so special , but if you don't like the music , the milestone doesn't really matter.There is a whole lotta jazz out there,Miles Davis is just one guy.

Kind Of Blue is the soul and energy of the musicians, melting together to form a record that you can really feel deep inside. If you are not familiar with Miles Davis, I highly recommend listening to some of his previous (before KOB) work to understand the build-up to this masterpiece.

I only play the LP, not the cd, and I am in complete awe of it. I love side one in particular. Describe your stereo system, maybe it's not optimized for realistic reproduction of acoustic instruments?

I tried playing a cd of Kind of Blue in my car and was totally bored by it. At home on my tube stereo I am transfixed.

Art

Brian's response kinda nailed it, intellectually, the playing in modes thing was new to jazz. Kinda Blue was from 58 or 59 though..you might actually find the earlier stuff a bit more to your liking, albums like Workin', Cookin' Steamin', Relaxin' are from 56 as I recall, and are more blues and popular tune oriented, jazzy versions of the days pop songs...try Some Day My Prince Will Come...Credit pianist Bill Evans for opening up Miles to more challenging chords & rhythms. He is a big part of the Kinda Blue sound. In my musical journey, something I don't like the first time I hear it, I've learned a few years later my ears are big enough to appreciate it. Especially in jazz I've developed an ear for things over time. I'd keep that Cd and try it again down the road, or listen to it over & over so the tunes become imprinted, then it is like you are playing along. I've bought this title several times over the years as formats or mastering has improved, definitely a classic. As an aside there is a CD title So What, one of the tunes on Kinda Blue, it is on Acoustic Disc by Jerry Garcia and David Grisman, this style of jazz played on acoustic guitar & mandolin, with rhythm section. Great album.... These compositions have become classics and are cool even without the horns!