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The mandatory Thelonious Monk Phase...

I think there's a temptation to assume that this stuff just flowed out of Monk instinctively almost like some kind of idiot savant but it does him a disservice not to recognise his intellect and the determination with which he applied it.

There's a solo version of the old clunker Tea For Two on the 1956 Prestige album The Unique Thelonious Monk which is one of the best illustrations of exploring musical language I know. He dissects the tune in real time and completely rearranges it in multiple ways. It's modernism in motion. Incredible stuff. He was extraordinarily smart.
 
Not much to add to what has been said except avoid the very late Monk. He sounded very tired by then but almost everything else was worth listening to

One of my favorite live Monk is Live at the It Club with Rouse in great form. Mosaic did a nice record box a while back but the used Columbia CD version should not be too difficult to find.

Also, watch Straight No Chaser if you can. I am still looking for a good dvd copy.
 
A quick count reveals I have 26 Monk albums. He’s definitely one of my mainstays along with Evans, Ellington, Mingus, Armstrong & Davis; I probably listen to the latter the least these days though.
 
As a life long Monk enthusiast I have to disagree with Tony about the Black Lion London Sessions.
The old boy is full of enthusiasm and was always at his best with Blakey’s assistance. He was becoming even more withdrawn by this time living mainly in the Baroness’ menagerie. A wonderful reprise.
The piano sound is so fine you can tell which recordings were made after they cut his fingernails.
I did see/hear the quartet once.Sadly most of it lost to memory but I do remember he took one of his dances around the stage.

Try Herbie Nichols or Elmo Hope both of whom showed a stylistic affinity to Sphere.
 


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