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Not saying the reasons are valid or anything but still... First, dude was undeniably a pioneer and revolutionary in the bebop era and in his own way, just as radical as Charlie Parker. However, Parker for some reason-his more "interesting" life perhaps?-has completely overshadowed him.
Also, he didn't really make the transition from Bop to post-bop/whatever that Miles, Mingus,Coltrane etc. made and as a result, his artistry might sound a bit more "old-fashioned" than those guys; overall, it seems to me that people today are primarily into jazz from the hard-bop and post-bop and fusion-eras.
His vocals and "entertainer"-aspects is another thing that works against him when Miles is viewed as the epitome of "cool" and super-serious searchers like Coltrane or troubled/mentally instable weirdos like Monk and Mingus is what people seem to dig image-wise; he was maybe a bit too "Louis Armstrong" so to speak...
That being said, his experiments with Cuban music as well as be-bop in a big band context and other stuff are incredibly cool IMO and important/influential/whatever; he was very early in terms of that kind of shit. It might sound too "populist" though for people who view guys like Sun Ra and Pharoah Sanders or even Yusef Lateef as the textbook examples of how "non-jazz" music should be incorporated in a jazz-context or Mingus as the quintessential "modern" big band guy (or Duke as the quintessential "old school" big bander).
That being said, dude definitely gets props but it is primarily for being a bebop innovator and unlike Monk, he didn't really take that style next level unless you count his and into the 50's-60's and unlike Miles, he didn't transcend numerous different eras and unlike Mingus (and Miles), he didn't make the big "important" album-statements and unlike Coltrane, he was never viewed as the poster dude for a new way of playing jazz (as I said, Parker occupies that space in bebop).
Basically, the older an artform gets, more and more important artists gets tossed to the side with every decade and while some people get some revisionist, cult-level appreciation, Dizzy was a bit too "mainstream" and successful for that too... It's sad but understandable as well, especially for an artform as marginalized as jazz... Note that it is happening in rock and soul and practically every other genre as well though.
Still, I wouldn't really view him as underappreciated like that though, he *is* a legend but you are right that his status is not on the level of other artists and it might be a bit undeserved in his case; I'm definitely a fan. I remember in the early 90's going to the library and borrowing a double-lp that compiled his big band and afro-cuban stuff from the late 40's-early 50's and it is some of the most fun music I've heard not to mention creative and brilliant and blah-blah...
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