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.