I do think that Kind of Blue is overrated (sacrilege in the jazz world), but a lot of its greatness is contextual. Its an amazing album, i just don't like it That much. IMO A Love Supreme by John Coltrane is by far the biggest masterpiece in all of Jazz. an album conceptualized and arranged by Coltrane as an instrumental praise to god for turning his life around after he'd defeated his heroin and alcohol addiction. The album, again IMO, is perfect in every way, shape, and form and is easily one of the most beutiful pieces of music iv'e ever heard.

Kind of Blue is a great record, Miles is smooth and melodic.
To be honest there are many other people on that record who I prefer to listen to like Bill Evans and John Coltrane.
What's the greatest is very subjective.

For my money some of my favourites are:

Sonny Rollins "Saxophone Colossus"
John Coltrane "Giant Steps"
Thelonious Monk "Brilliant Corners"
Art Blakey and the Jazz Messengers "A Night in Tunisa"
Anything with Charlie Parker on it.

All in my opinion much greater Jazz records.
For me "Kind of Blue" is a bit more easy listening.

Probably ,after A Love Supreme, the next 4 of my top 5.

Yeah Love supreme is supreme.

I'd also chose Clifford Brown's trumpet playing over miles's every time.
Check out "Jazz immortal" he could play circles around miles.
Too bad he died at 25 we never found out his true potential.

Miles became a legend partly by a war of attrition. He outlasted so many of his contemporaries. He was the great band leader he was lucky to play with all the greats of Jazz. His alumni includes.

Charlie Parker (1940s)
John Coltrane (1950s)
Bill Evans (1960s)
Charles Mingus
Horace Silver
Sonny Rollins (1950s)
Marcus Miller (1980s)
John McLaughlin (1960s)
Herbie Han**** (1970s)
Billie Cobham (1970s)
Thelonious Monk (1940-50s)

Those are just the first of my favourtes of his bandmates that pop to my mind. There must be hundreds and hundreds.

He was one hell of a bandleader!!

I'm a huge Clifford Brown fan. I can hardly fathom what music would be like today if he hadn't gotten into that car. BTW, Scott Lafarrow, the bassist for The Bill Evans Trio, AKA the upright player on Portraits in Jazz, also had an untimely death via a car accident, and is from my hometown. I used to drive past the scene of his accident daily on my way to school.

My opinion on this hasn't really changed over the last 15 years. I just had another listen and really I think Blue in Green and Flamenco Sketches are the highlights as they have lots of feeling and some interesting turns of phrase at times. The rest though feels like filler, undemanding but sounding beautiful enough to make it ok for those who don't listen to much jazz and just want something that sounds nice.

As for best jazz album, why does there have to be a 'best'? Things can be good in different ways, it's just a marketing thing to say something is the 'best' out of everything. Kind of Blue does seem overrated however, but perhaps mainly by those who don't know much jazz.

An interesting article here:
Kind of Blue, Reloaded | Blue Music Group

Kind of Blue is amazing, but not even my favorite Miles. A tentative MD-top three:

1) In a Silent Way
2) On the Corner
3) Sketches of Spain

Taste and stuff probably. It's mainly just the moods on those three records that I find better than on the other ones I've heard. So much greatness in his ouvre.

Hmmmmm
 

Dave Holland, Conferences
Mike Garson , Now Music Vol Iv
Theo Monk , Live in Tokyo

"Kind Of Blue".. is a must have..

"A Love Supreme".. (John Coltrane)..
"Maiden Voyage", "Empyrean Isles".. (Herbie Hancock)..
"Rainbow Seeker".. (Joe Sample)..

Quickly off the top of my head:

1) The Black Saint and the Sinner Lady
2) A Love Supreme
3) Sunday at the Village Vanguard

Kind of Blue is definitely up there though.

What a terrible tragedy, he was only in his twenties too, I think. His work with Bill Evans at the Village Vanguard is some of the best bass playing I've ever heard!