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Start here with Monk!,
This review is from: The Best of Thelonious Monk: The Blue Note Years (Audio CD)
This is the place to start if you're looking into the music of the great Thelonious Monk. Collected here are more of Monk's compositions in concentrated form than in any other place. There are many later versions of many of them, including of course by other musicians such as Steve Lacy, but these are the first recordings, the templates. You can hear the structure of the music more clearly than in any of the great Riverside records such as Brilliant Corners.
As the liner notes say, Monk's music is "always off center, but it always swings." "Well You Needn't," "In Walked Bud" and "Straight No Chaser" are up-tempo and catchy as hell -- you won't be able to get them out of your head. "Misterioso" sounds just like the title -- fractured, odd piano, and vibes. Listen closely to "Skippy" and hear why no one attempted to cover it for 30 years!
"Monk's Mood" is gorgeous, slow and romantic. I first heard it on Jack DeJohnette's "Album Album" (1984) with David Murray and John Purcell on sax, an incredible version now available in an ECM box: Jack DeJohnette Special Edition. Of course "Round Midnight" quickly became a standard, an ineffably sad ballad covered by Miles among many others.
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Here's a fun piece of trivia -- the recording engineer for these sessions is Harry Smith. Yes, it turns out, it is THAT Harry Smith, the guy who compiled the famous Anthology of American Folk Music, recently reissued by the Smithsonian Institute. Smith used to project light shows of his own creation as accompaniment to jazz shows in the Bay Area!