10 Essential Miles Davis Albums

Miles Davis, 1960.

Miles Davis backstage, 1971.

Collage of the album covers for 9 of the 10 Essential Miles Davis albums I wrote about in this post. Sorry "Live in Europe 1967," your album cover was the one I decided was most boring.

Miles Davis is one of the towering figures in the history of jazz. I’ve written about some aspects of his music before, like a review of Ashley Kahn’s excellent book about Davis’ classic 1959 album “Kind of Blue,” and a general overview of his music in the 1950’s and 1960’s. I also wrote in-depth reviews of the three albums Davis recorded in 1961, when tenor saxophonist Hank Mobley was in his band: “Someday My Prince Will Come,” “In Person Friday and Saturday Nights at the Blackhawk,” and “Miles Davis at Carnegie Hall.” Because Davis’ discography is so vast, it can be difficult to know where to start with his music. Davis played many different styles of jazz throughout his career, and just because you like one of his styles is no guarantee that you’ll like all of his music. Here’s a list of what I consider to be 10 of Miles Davis’ greatest albums. This list is subjective, and there are many excellent albums I’ve left off, but I’ve tried to pick the best of Davis’ various styles. No matter which style of Miles Davis you prefer, you should find something you’ll enjoy here. The albums are listed in the order they were recorded. 

“Bags’ Groove,” recorded 1954. Davis started recording with the great alto saxophonist Charlie Parker in November 1945, when he was just 19 years old. After several years in Parker’s group, Davis left to begin a solo career. In 1949 and 1950, Davis was the leader for the influential “Birth of the Cool” album, which helped to usher in a quieter, more subdued style of jazz called "cool jazz" or "West Coast jazz." Miles was heavily influenced by classical music, and the "Birth of the Cool" sessions were the antithesis of frenzied bebop soloing. One of the featured members of the "Birth of the Cool" band was Gerry Mulligan, who formed a group with the trumpeter Chet Baker that achieved great success in the early 1950's. Unfortunately, like many other jazz musicians of the period, Davis had developed a crippling heroin addiction. Once he finally got clean in early 1954, Davis began making an excellent series of recordings for Prestige Records. These records pointed the way towards hard bop, which was in some ways a reaction to the prevailing West Coast “cool” style that Davis himself had helped to usher in. “Bags’ Groove” is a killer set of hard bop, recorded when Miles was finding his own voice as a leader. The band Miles worked with on this record was insanely talented. On the song “Bags’ Groove” the band was Davis, Milt Jackson on vibes, Thelonious Monk on piano, Percy Heath on bass and Kenny Clarke on drums. On the other tracks it was Davis, Heath, Clarke, Sonny Rollins on tenor sax, and Horace Silver on piano. The album features three songs by Sonny Rollins that would become jazz standards: “Airegin,” “Oleo,” and “Doxy.” 

“Cookin’ with the Miles Davis Quintet,” recorded 1956. After his triumphant comeback performance at the Newport Jazz Festival in 1955, Davis put together a band of his own. He found one of the greatest rhythm sections in jazz history; pianist Red Garland, bassist Paul Chambers, and drummer Philly Joe Jones. And he took a chance on a journeyman tenor sax man from Philadelphia: John Coltrane. Miles and Trane's partnership would change the course of jazz history. This band was known as Miles's first "Classic Quintet," and the recordings they made together set the standard for hard bop playing. Davis was being courted by major record labels, and he worked out a deal with Columbia Records where he could record for Columbia during 1956 while he fulfilled his remaining obligations to Prestige Records. “Cookin’” was one of four albums he and the quintet recorded over two days for Prestige, and it features Miles’ famous recording of “My Funny Valentine,” one of his signature songs. Davis was crafting his trademark sound on the trumpet, and part of that was his use of the Harmon mute on ballads, which gave his sound an intimate, late-night feeling. 

 “Milestones,” 1958. Davis released his first album for Columbia Records, “’Round About Midnight,” in 1957, and it proved to be the beginning of a relationship that would last until 1985. At the end of 1956, Davis had actually fired Coltrane because of his drug problem, and had disbanded his quintet. Coltrane got clean and spent most of 1957 playing with Thelonious Monk. By the end of 1957, Davis had re-formed his quintet, with the addition of alto saxophonist Cannonball Adderley, making it a sextet. It is this group that recorded the classic album “Milestones.” “Milestones” is inevitably overshadowed by the much more famous “Kind of Blue,” but it is a fantastic album in its own right. Miles plays piano on “Sid’s Ahead,” as Red Garland had left the studio in a huff. “Milestones” features some great hard bop playing on the title song and “Straight, No Chaser.” The music on “Milestones” points the way forward to the modal structures of “Kind of Blue.”

“Kind of Blue,” 1959. It’s not really a surprise this album would make the list. “Kind of Blue” is a classic album that is actually worthy of all the acclaim it has received. Regularly hailed as “the greatest jazz album ever,” “Kind of Blue” found Davis and his entire group at a peak of creativity. Davis’ band on “Kind of Blue” was Coltrane on tenor sax, Cannonball Adderley on alto, Bill Evans on piano, (Wynton Kelly plays piano on “Freddie Freeloader”) Paul Chambers on bass, and Jimmy Cobb on drums. Evans had actually already left Davis’ group by the time “Kind of Blue” was recorded, but he returned for the album sessions, and he played a key role in helping Davis shape the music and sound of “Kind of Blue.” Evans claimed that he co-wrote “Blue in Green” and “Flamenco Sketches” with Davis, although he isn’t given co-writing credit. There was no way that Davis could keep a group full of so many jazz superstars together for very long, and within a year both Coltrane and Adderley had left to lead their own groups. Miles never made another album exactly like this one. One of the things I admire the most about Miles Davis is how he kept changing his music. He never stood still; his sound was always shifting and evolving. He could have taken the easy way out and tried to recapture the sound and magic of “Kind of Blue,” but he didn’t. Davis’ sound on the trumpet was so gorgeous that he could have made a ton of money by churning out smooth jazz albums where he just played pretty ballads, but he never did that, and I admire that about him. 

“Sketches of Spain,” 1960. Miles’ third collaboration on Columbia with arranger Gil Evans produced this album that featured some of Davis’ most beautiful playing. Davis’ albums with Evans are some of the most successful albums pairing a jazz performer with a large orchestral ensemble. Their previous collaborations were the highly esteemed “Miles Ahead” and “Porgy and Bess.” I like Davis’ small group albums more than his work with Evans, but “Sketches of Spain” is my favorite of their albums together. 

 “Miles Smiles,” 1967. In the early and mid-1960’s Davis had a number of health problems, including undergoing a hip replacement in 1965. When he entered the studio in October 1966 to record “Miles Smiles,” it was his first recording session since January 1965. The group he was recording “Miles Smiles” with was his “Second Classic Quintet” featuring Wayne Shorter on tenor sax, Herbie Hancock on piano, Ron Carter on bass, and Tony Williams on drums. “Miles Smiles” was their second album together, and it showcased this group at the peak of their powers. Miles was musically rejuvenated by his young sidemen, and “Miles Smiles” highlights Shorter’s gifts as a composer, as he wrote “Orbits,” “Footprints,” and “Dolores.” “Circle” is a beautiful song, and one of Miles’ last great ballads. 

“Live in Europe, 1967: The Bootleg Series Volume 1,” recorded 1967. Not released until 2011, this three disc set features Davis’ “Second Classic Quintet” live in concert and shows all of them stretching the boundaries of jazz. The sets flow seamlessly, and the group has great chemistry together. As usual with Davis’ groups, all of these players are excellent soloists. The young, hyperkinetic drummer Tony Williams pushed the band to new heights on uptempo songs. We’re fortunate these performances were recorded, and in such good quality.

“In a Silent Way,” 1969. Miles Davis’ music changed very quickly in the late 1960’s. His “Second Classic Quintet” made their last recording together in 1968, as bassist Ron Carter left the group. Davis began to record with electric instruments and experiment with more open song structures. He was also starting to play music that was influenced by funk and soul. All of these new developments would eventually lead to the “fusion” style of jazz. Davis also started recording with larger groups, and the band on “In a Silent Way” features three keyboardists. “In a Silent Way” was the first record of Davis’ featuring British guitarist John McLaughlin, who would be an integral part of the sound of Davis’ music over the next few years. The music on “In a Silent Way” is unlike anything else Davis ever attempted. It’s moody, ethereal music that floats in the air. It’s an excellent late night album that slowly works its spell on you. 

“Bitches Brew,” 1970. You’ll either love it or hate it. But whatever you think of “Bitches Brew,” it’s definitely one of Davis’ key albums. “Bitches Brew,” Davis’ most famous jazz fusion album, may have alienated jazz purists, but also appealed to fans of rock and roll. I resisted fusion for a long time, not hearing anything but clutter in it. But a few years ago I finally decided, “I need to buy this album and really listen to it.” I enjoyed “Bitches Brew” more than I thought I would. It’s not my favorite Miles Davis album, but it was a landmark album, and helped change the direction of jazz, for better or worse. 

“Jack Johnson,” also known as “A Tribute to Jack Johnson,” 1971. Recorded as the soundtrack to a documentary film about Jack Johnson, the African-American heavyweight boxer, “Jack Johnson” is a rocking album that is full of heavy funk. It’s a groovier ride than “Bitches Brew,” and I prefer it to “Bitches Brew.” At the time it was not very successful commercially, but its reputation has grown over the years. Filled with two side-long jams that feature great guitar work from John McLaughlin, it’s perhaps Davis’ best fusion album. Herbie Hancock’s appearance on the album was serendipitous, as he just happened to be passing through the Columbia studios building and was recruited by Davis to play organ.

There you have it, 10 essential albums by Miles Davis. Yes, there are many classic albums not represented here. But these 10 albums will give you a good idea of why Miles Davis was so important to music.

Book Review: "Kind of Blue: The Making of the Miles Davis Masterpiece," by Ashley Kahn

"Kind of Blue: The Making of the Miles Davis Masterpiece," by Ashley Kahn, 2000.

John Coltrane, Cannonball Adderley, Miles Davis, and Bill Evans at the session for "Kind of Blue," 1959.

I just finished Ashley Kahn's 2000 book, "Kind of Blue: The Making of the Miles Davis Masterpiece." It's a terrific read, and I would recommend it to any jazz fan, or anyone who is interested in learning more about how this remarkable album was created.

To anyone who doesn't know, Miles Davis's 1959 album "Kind of Blue" is widely regarded as the greatest jazz album ever. It's a landmark of small group jazz improvisation as its finest. The band Miles assembled was one of the greatest ever. On the album, Miles started to explore modal jazz, a very different way of playing jazz. In his book, Kahn explores Miles's career during the 1950's, and what led him to make the album.

Kahn did a great job of researching this book, and he interviewed Columbia Records photographer Don Huntstein and drummer Jimmy Cobb, the only two people still alive who actually witnessed the recording sessions. Sadly, when pianist Bill Evans died in 1980, just twenty-one years after the album was recorded, that left only Miles and Jimmy Cobb still alive from the "Blue" band. Which is really odd, considering that Miles was the oldest member of the band in 1959, at just 32 years old. John Coltrane died at age 40 of liver cancer in 1967, bassist Paul Chambers died at just 33 of tuberculosis in 1969, Wynton Kelly died at 39 in 1971, and Cannonball Adderley died in 1975 at 46.

Kahn should be praised just for the simple fact that we actually get some insight as to how this classic album was made. The answer is, pretty easily, at just two recording sessions. There was only one complete alternate take from the sessions, an earlier version of "Flamenco Sketches." But that doesn't mean that these were all first-take performances, despite what Bill Evans claimed in the liner notes. Miles would end takes if they weren't going well, giving the players terse directions.

Pianist Bill Evans is probably the person other than Miles most responsible for how "Kind of Blue" sounds. Miles even said, "I wrote that album around Bill Evans's piano playing," even though Evans had quit as a member of Miles's working band by the time of the sessions. Both Evans and Davis loved classical music, even though Evans had more classical training. (Miles had quit Juilliard after just one year.) Davis would often spend time checking out classical scores from museums and libraries, and didn't understand why he couldn't get other jazz musicians to accompany him. But in Evans he found someone similar to explore his ideas with. Miles wrote of Evans in his autobiography, "Bill had this quiet fire that I loved on piano. The way he approached it, the sound he got was like crystal notes or sparkling water cascading down from some clear waterfall." Which would also be an accurate way of describing Miles's playing style in the late 50's. Since Miles was not an explosive bop virtuoso like Dizzy Gillespie, he had to get his playing across in a different way. So he started using space more in his solos, (influenced by the pianist Ahmad Jamal) and playing fewer notes to get the emotion of a piece across. He also started playing in the middle register of the trumpet more, as opposed to players like Dizzy who would fire off a rapid series of extremely high notes. Miles also started using a Harmon mute on ballads, which gave his playing a breathy, smoky, late-night sound.

According to Evans, he and Miles wrote "Blue In Green" and "Flamenco Sketches" together, despite the credits on the album listing Davis as the sole writer of all the tracks. When Evans recorded a version of "Blue In Green" for his own album, "Portrait in Jazz," he insisted that his name be listed alongside Davis's as co-writer. Both songs sound like Evans, and it would seem likely that he got screwed out of his writing credit. But Evans also kind of screwed himself out of his credits, as he wrote the liner notes to "Kind of Blue," and in them doesn't make any mention of his co-writing role. Who knows what really happened between Davis and Evans, but a telling factor would be that Miles never performed "Blue In Green" and "Flamenco Sketches" live, at least not on any known recordings. (He also never did "Freddie Freeloader" live, which seems odd because of its bluesy structure.)

The alchemy that made "Kind of Blue" possible never came together again. Evans had left Miles to form his own trio, and within a year Cannonball and Coltrane had each formed their own groups. And Miles didn't seem interested in revisiting former glories by trying to record another album with the same sound. "Kind of Blue" would remain a unique masterpiece in jazz history. And thanks to Ashley Kahn's book, we get to feel like we were there at the creation.

Miles Ahead: An Essay on the Music of Miles Davis

Miles Davis

Miles Davis was an incredible musician. Okay, now we're finished with the understatement of the day. I'm reading Ashley Kahn's book "Kind of Blue: The Making of the Miles Davis Masterpiece," and I'm amazed by the success Miles had in so many different styles of jazz. He certainly wasn't content to rest on his laurels. As soon as he had success in one field of jazz, he was on to a different challenge. He was on the cutting edge of jazz for 20 years, pioneering several important jazz movements.

Miles started out playing with Charlie Parker in the late 1940's. Parker was one of bebop's biggest stars at the time, and Miles was some kid just out of East St. Louis. But Parker took Miles under his wing. But just as Miles was making his ascendancy in the world of bebop, he changed styles. He made the album, "The Birth of the Cool" in 1949-50 that ushered in a quieter, more subdued style of jazz called "cool jazz" or "West Coast jazz." Miles was heavily influenced by classical music, and the "Birth of the Cool" sessions are the antithesis of the frenzied bebop soloing. One of the featured members of the "Birth of the Cool" band was Gerry Mulligan, who formed a group with the trumpeter Chet Baker that achieved great success in the early 1950's. But Miles didn't make any more records like "Birth of the Cool," at least not until his sessions with Gil Evans. (Who arranged some of the "Cool" sides.) Once Miles got his act together again, and kicked his heroin addiction, the records he made in 1954-55 pointed the way towards hard bop, which was in some ways a reaction to the prevailing West Coast "cool" style that Miles himself had helped usher in. He lead all-star sessions for Prestige records that produced classics like "Bag's Groove." The lineup on "Bag's Groove" is a who's who of 50's jazz: Sonny Rollins, Thelonious Monk, Milt Jackson, Horace Silver, Percy Heath and Kenny Clarke. Wow.

In 1955, Miles set about putting together a steady group he could lead. He found one of the greatest rhythm sections in jazz history; pianist Red Garland, bassist Paul Chambers, and drummer Philly Joe Jones. And he took a chance on a journeyman tenor sax man from Philadelphia: John Coltrane. Miles and Trane's partnership would change the course of jazz history. This band was known as Miles's first "Classic Quintet," and the recordings they made together set the standard for hard bop playing. And then Miles fired Coltrane because of his heroin addiction. (Trane got clean in 1957, played with Monk for 6 months, and then Miles re-hired him.) Miles also made the decision to record an album with a large ensemble arranged by Gil Evans, it would be called "Miles Ahead." The albums Miles made with Gil Evans aren't my favorites, but the people who like them really like them, and they are considered the best albums of their kind. Miles was changing things up yet again.

On his 1958 album "Milestones," Miles added alto sax player Cannonball Adderley to the group, and started the path towards modal jazz, which led to "Kind of Blue." I can't claim to totally understand all the differences between modal jazz and non-modal jazz, but I think it boils down to this: in modal jazz, you improvise with or against the scales, not the chords, as in most styles of jazz. In a modal song, you might only have two chords, so you can't improvise with or against the chord changes. This was the opposite of bebop, where the chord changes were everything. It was a totally different way of improvising. (This really sounds like I know what I'm talking about, doesn't it?) Anyway, from what Kahn says in his book, that's how I understand it.

The gold standard for modal jazz was Miles's 1959 album "Kind of Blue." It's regularly cited as the greatest jazz album ever, and even shows up in rock magazine polls of great albums. If you haven't heard it, go out and buy a copy. Right now. When you've finished listening to it, please return to this blog entry and keep reading. I'll wait for you...done? Wow, wasn't it great? Again, Miles put together an amazing band full of musicians who would continue to make great jazz as solo artists. The "Kind of Blue" group was: Miles, Cannonball Adderley, John Coltrane, Bill Evans, Wynton Kelly, Paul Chambers, and Jimmy Cobb. Wow. Within a year, Cannonball and Coltrane had both formed their own groups, as had Bill Evans. (Evans technically left Miles's group in late 1958, but returned for the "Kind of Blue" recording.)

But rather than keep plowing the modal fields until nothing was left, Miles kept changing his sound. He never made another album that sounded like "Kind of Blue." In 1963, Wynton Kelly left, taking Paul Chambers and Jimmy Cobb with him to form their own trio. Miles had to form a new band, from the ground up. Eventually, in 1964, the new lineup became Wayne Shorter on tenor, Herbie Hancock on piano, Ron Carter on bass, and Tony Williams on drums. This group became known as Miles's second "Classic Quintet." Miles's playing became harsher during this period, as some of that ballad softness seemed to slip away. By 1968-69, Miles was experimenting with more open song structures, electric pianos, and grooves influenced by James Brown and Jimi Hendrix. It was the start of fusion, heralded by Miles's albums "In a Silent Way" and "Bitches' Brew." I have to confess, I don't like fusion. I don't really get it. But I can understand that it was an important movement in jazz, and once again, Miles was on the front line, leading the charge.

Miles's music post-1969 doesn't hold a lot of appeal for me, and from what I've read, it doesn't sound like he broke a lot of new ground after fusion. But that really doesn't matter, because in twenty years at the forefront of nearly every major movement in jazz, Miles had broken enough boundaries for many lifetimes. Honestly, most artists, in any genre, don't get to say they started or heavily influenced as many different styles as Miles did.

So those are some of my thoughts on Miles Davis, one of my favorite jazz musicians. I'm just intrigued by the way he kept searching, kept moving. He could have tried to make 10 albums just like "Kind of Blue," but he didn't, which I admire. Miles did not do things the easy way, and he definitely did them his way.