Here are 10 albums from Miles Davis that in my opinion make an excellent "primer" of his overall body of work. These are not necessarily the 10 Miles Davis albums I consider to be "the best" but rather the 10 that I feel best capture the various aspects and important phases of his long and very influential and innovative career. I've tried to take into account the albums' accessibility, quality and how representative they are of the particular phase from which they're drawn.
1. Birth of the Cool - Collection of cool jazz sides recorded in '49-'50 with larger ensembles. As the title indicates, it was instrumental in the development of the cool jazz sound, which distinguishes itself from bop/bebop by generally using slower tempi, larger, more orchestral ensembles and an overall lightness of feel. Another noteworthy thing about this collection is that it gives us Miles' first collaboration with conductor/arranger Gil Evans, with whom he would record several times later in a wholly different but also widely acclaimed style. More on that later.
2 & 3. Volume 1 & Volume 2 - Early recordings for the legendary Blue Note label. Miles has left cool jazz behind by this point, this represents a move toward bop/hard bop and finds Miles recording with the likes of Art Blakey, Jackie McLean and Horace Silver. Great stuff recorded between '52-'54.
4 & 5.Milestones & Kind of Blue - Milestones (1958) is Miles flirting with modal jazz, the apotheosis of which is the following year's Kind of Blue. The Milestones quintet is basically the same as Kind of Blue's (John Coltrane, Philly Joe Jones, Cannonball Adderley, Paul Chambers) except Red Garland is on piano instead of Bill Evans, whose contributions to Kind of Blue were immense (so much so that a box set issued under Evans' name was called [albumartist=Bill Evans]Kind of Evans[/album]) and who played on all of its tracks except the blues number "Freddie Freeloader." Kind of Blue is considered to be one of the greatest jazz albums of all time and rightly so. I think it would commonly be said that if you only own one Miles Davis album it should be Kind of Blue.
6 & 7. [albumartist=Miles Davis]Miles Ahead[/album] & [albumartist=Miles Davis]Porgy and Bess[/album] - These are two of the great third stream (a blend of Western Classical music and Jazz) that Miles made with Gil Evans, who handled the arrangements of the orchestra who plays along with Miles on these albums. Both are classics. Many people might include [albumartist=Miles Davis]Sketches of Spain[/album] as a better example of this style than one or both of these records but to my mind it's not quite of the same quality, though it is still good and worth buying/hearing.
8-10. [albumartist=Miles Davis]Miles in the Sky[/album], [albumartist=Miles Davis]In a Silent Way[/album], [albumartist=Miles Davis]A Tribute to Jack Johnson[/album] - Miles in the Sky is the first album where Miles begins to incorporate "electric" instrumentation but it isn't quite a fusion album, instead falling under the heading of post bop, which no one really knows how to define exactly. Anyway, it's a transitional album that doesn't have quite the iron-clad critical reputation that some of the surrounding stuff does, but it's great; the band includes Herbie Hancock, Wayne Shorter and Ron Carter. In a Silent Way and (A Tribute to) Jack Johnson are both full-blown "electric" albums that include, among others, Hancock, John McLaughlin and Chick Corea contributing. Both are masterpieces; In a Silent Way has a spacier sound to it -- and is in fact sometimes described as space music -- while Jack Johnson is the most Rock-influenced thing Miles ever recorded in the studio.
So, there's 10 great albums to get you started on a nice Miles Davis kick. I did not include [albumartist=Miles Davis]Bitches Brew[/album] because it's 90 minutes long and in my opinion is not a good starting point for someone who doesn't yet understand Jazz/Fusion/Miles Davis; I think in jumping into that one you'd find yourself overwhelmed and end up disliking an artist/some music you might otherwise really come to enjoy. I also didn't include [albumartist=Miles Davis]On the Corner[/album], which you may see on various "top albums" lists (Pitchfork, for one, included it on their Top 200 of the 1970s list some years because I personally don't feel that it's a first-rate Miles album and I don't think it's as critical in his development as the others I've listed; it is pretty good but it doesn't have much in the way of vital compositions nor is the band Miles has surrounded himself with as high quality as on the albums I've listed above (only Chick Corea and Herbie Hancock are first rate players of those in the On the Corner band, in my opinion).
I consider the albums Miles and his first great quintet (Paul Chambers - bass, Philly Joe Jones - drums, John Coltrane - tenor saxophone, Red Garland - piano) recorded for the Prestige label -- [albumartist=Miles Davis]Cookin' with the Miles Davis Quintet[/album], .[albumartist=Miles Davis]Relaxin' with the Miles Davis Quintet[/album], [albumartist=Miles Davis]Workin' with the Miles Davis Quintet[/album], [albumartist=Miles Davis]Steamin' with the Miles Davis Quintet[/album] -- to be among the peaks of the Hard Bop subgenre as a whole, but since the albums were all recorded at the same sessions and are virtually indistinguishable from one another both stylistically and in terms of quality, and since there are four of them and I wanted to limit this ilst to exactly ten albums, I didn't include them. If you're already familiar with Bebop/Bop/Hard Bop but not Miles, I'd suggest jumping right in with any or all of these four. Volumes 1 & 2 are great collections that chart Miles' development in a fascinating way but these four quintet albums are uniformly excellent.
As with any great musician who is both a big name and who had a long career, there are a number of tossed-off compilations and live albums out there that aren't worth a damn. Generally the compilations have titles like "Miles for Lovers," "Mellow Miles," etc. These types of things are useless and all but defeat the purpose of listening to Miles Davis. Jazz is different from other genres in that many live albums are actually very good, since much of the point of Jazz lies in group and individual improvisations, soloing, etc. However, there are a lot of labels out there that are unscrupulous as hell, taking audio of poor sonic quality, slapping a title referencing a well known Miles song on there and charging a hefty price tag for it. Much of the time these unscrupulous labels will re-release the same live recordings that have been released under similar circumstances previously, making it easy for the unsuspecting customer to end up with a lot of not just mediocre material but duplicated mediocre material. A good wa to avoid this with Miles is to stick to releases by labels like Blue Note, Prestige and Columbia/CBS. Maybe sometime I'll do another part of this list that includes his best live albums or something.
I think that's it for now. Enjoy!