Miles Davis was a true jazz lovers — jazz musician. Well, if the criteria is that he was never very popular with mainstream music buyers. Unlike other jazz greats like Louis Armstrong, Stan Getz, Dave Brubeck and Cannonball Adderley, Miles Davis never had a hit record in spite of releasing 57 singles. He had just a few albums that charted in the top 100. So no, Miles Davis never crossed over into popular music circles.
Supposedly, you have to really know something about jazz to understand his music. Which is too bad because he did record a whole heck of a lot of accessible music. And he did create the best selling jazz album of all times. Sure there are all these categories when looking at Miles: Bebop, Cool Jazz, Hard Bop / Post Bop, Modal jazz, Jazz Rock / Fusion and orchestral / third wave music. But in the end they are just names. What matters is the music. And Miles Davis produced some truly great music. And amongst the best of the best is Kind of Blue, that five times platinum album.