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Our Top Ten: The essential Miles Davis albums

Miles Davis performing at Newport Jazz Festival in 1969.
David Redfern
Miles Davis performing at Newport Jazz Festival in 1969.

On May 26, 2023, Miles Davis would have turned 94 years old. The brilliant trumpeter and bandleader was only 65 years old when he died in 1991. But during a career of under five decades, he managed to change the direction of jazz at least that many times, albeit with the help of gifted collaborators along the way, like Gil Evans, Wayne Shorter, Herbie Hancock, Marcus Miller and many others.

So coming up with a short list of essential albums in his catalog makes for an interesting challenge. In this case, I went with both critical mass as well as gut feel, relying on my own four decades as a fan and listener. We listed the albums in chronological order, rather than pick a number one through ten. After all, as several of our listeners pointed out on social media, choosing your favorite Miles Davis album can depend on the time of day or your emotional mood.

We loved hearing from our listeners and followers about their favorites. We’ve listed their choices, beyond my ten recommendations, below.


It Never Entered My Mind

Workin’ (1956)
The material for this album comes from two recording sessions in 1956, done clearly to fulfill contractual obligations to Prestige Records, so that Miles could move on to a more lucrative deal with Columbia Records. Jazz musicians and scholars of subsequent generations would nonetheless view these recordings as forming a virtual Rosetta Stone for post-bop jazz. One reason was that the band featured one of his great quintets with John Coltrane, Red Garland, Paul Chambers and Philly Joe Jones. Music from those two sessions were pushed out by Prestige as four albums: Workin’, Steamin’, Cookin’ and Relaxin’. For some of us coming of age in the 60s and 70s, we were able to secure them as two-album sets, such that many of us can’t say Workin’ without Steamin’ or Cookin’ without Relaxin’. I chose Workin’ because of the tunes, such as “In Your Own Sweet Way,” “Half Nelson,” and the iconic version of “If I Were a Bell” which opens the record with Miles’ muted trumpet, soon to become his signature sound. Best of all with these four albums? There are a bunch of mistakes and missed notes. That just makes it all so much more enjoyable. Funny how these two knocked off recording sessions can still knock our socks off today.

Miles Ahead

Miles Ahead (1957)
This album, which featured Miles’ first collaboration with arranger Gil Evans since Birth of the Cool, has numerous notable qualities. First, Miles plays the flugelhorn exclusively throughout. Second, though backed by a stellar large ensemble featuring Lee Konitz, Ernie Royal, Wynton Kelly and 15 others, Miles is the only soloist throughout. Third, Evans manages to connect the 10 compositions into a seamless suite. The album would become a model for a new sub-genre of jazz – The Third Stream – which fuses jazz improvisation with classical composition and instrumentation.

Miles Davis - Milestones (Official Audio)

Milestones (1958)
Rightly seen as a precursor to Kind of Blue, Milestones featured the same group, albeit with Bill Evans later replacing Red Garland and Jimmy Cobb replacing Philly Joe Jones. Often pointed to as a model of modal jazz, the album features several compositions that would become standards in the jazz idiom, including the title tune by Miles, as well as Dizzy Gillespie and John Lewis’ “Two Bass Hit,” Jackie McLean’s “Dr. Jekyll,” and Monk’s “Straight No Chaser.” Yea, that last one would probably have been a standard without Miles’ modal take, but the stamp of approval remains. One of the subtle rewards for listeners is hearing the exchange and interplay between two very different and two very distinctive saxophonists with Trane and Cannonball. They both would soon become formidable leaders of their own, a pattern that happened so many time during Miles’ career.

Miles Davis - So What (Official Audio)

Kind of Blue (1959)
Here’s where I explain why this album is so popular and timeless. No. Read Ashley Kahn’s brilliant book about the making of the album. However, I will offer this one insight. Perhaps the most popular jazz album of all time had no follow up. None. That’s because each of the main featured players—Miles, Coltrane, Adderley and Bill Evans—went in entirely different directions immediately after. Miles would go on to his next great quintet that reinvented jazz yet again. Bill Evans would put his head down and explore the piano trio format for the rest of his life. Cannonball would bring gospel and soul into modern jazz. And Coltrane? Well, he ascended to heights that few at that time could have imagined. Who would have ever thought that the style of a hit album like Kind Of Blue would become like Kryptonite for the players? In many ways, that makes the album even more special. It was truly lightning in a bottle. One that continues to enrapture generation after generation of music lovers, well beyond the world of jazz.

Concierto de Aranjuez: Adagio

Sketches of Spain (1960)
It seems that every jazz horn player yearns to play with an orchestra, going all the way back to Charlie Parker and strings. Miles was certainly no exception but this album only feels like he’s playing with a string orchestra. The arrangements for the large ensemble are that exquisite. Gil Evans continued to work his magic with Miles on this recording featuring the adagio movement of the Concerto de Aranjuez, a concerto for guitar by the Spanish composer Joaquin Rodrigo, as well as “Will o’ the Wisp,” from Manuel de Falla’s ballet El amor brujo. Evans also arranged some Spanish folk songs for the second side of the album. The personnel included many of the same bandmember who had been on Miles Ahead and Birth of the Cool. In a theme that would repeat itself several times during Miles’ career, the album was poorly received by critics at the time, but later heralded as a masterpiece. Regardless of the critical response, the album further cemented Miles’ reputation as a soloist capable of remarkable melodic beauty.

E.S.P. (2022 Remaster)

E.S.P. (1965)
Honestly, I could have picked any of the recordings done over a seven-year period by Miles’ great, no greatest, quintet, featuring Wayne Shorter, Herbie Hancock, Ron Carter and Tony Williams. I chose this album because the band had really gelled at this point, playing both free and tight in a way that would influence multiple generations of jazz players. In addition, you can hear some rock and R&B rhythms that he would push forward into his music of the 70s. Yet another reason to pick this one up is the final appearance of Miles’ beautiful and talented wife Frances on the cover. Check out Stanley Nelson’s documentary Miles Davis: Birth of the Cool to see and hear her talk about their inspired yet volatile relationship. Regardless, you can’t go wrong with any of the albums Miles did with this band: Seven Steps to Heaven, Filles de Kilimanjaro, Nefertiti, Miles Smiles, Sorcerer and Water Babies. From E.S.P. you can go backward or forward, though, for his part, Miles always went forward.

In a Silent Way

In a Silent Way (1969)
Truly a bridge between Miles’ great quintet records of the ‘60s and his electric groove explorations of the ‘70s, this album’s title says it all. Or how about song titles like “Shh” and “Peaceful”? The title tune was originally written (and recorded) by Joe Zawinul, but Miles then stripped down in the arrangement for this album. The list of personnel reads like a who’s who of jazz rock, including Zawinul, John McLaughlin, Chick Corea, Herbie Hancock, Wayne Shorter, Dave Holland and Tony Williams but you won’t hear any pyrotechnic jazz fusion chops here. In fact, Davis famously instructed the virtuosic McLaughlin to play as if he had just picked up the guitar. The result on all accounts was beautifully simple. And simply beautiful.

Bitches Brew

Bitches Brew (1970)
Make no mistake. For many generations of jazz fans, this album was the proverbial line in the sand when it came to Miles’ long career. I can’t count the number of times I’ve heard “I loved Miles’ music until Bitches Brew but then he lost me.” As Miles famously said to a fan criticizing his new direction, “Why should I wait for you to catch up?” Once again, the album was both loved and reviled in its time, but it sold very well. In fact, the album still seems to provoke very different responses from critics and musicians alike with perhaps the late Stanley Crouch being its most vociferous and public critic, pontificating in the Ken Burns Jazz series as well as in the Electric Miles live concert video. No one can deny that with its rock and funk rhythms and electric instrumentation, the album well reflected its time. A time when jazz was losing its audience to rock, soul, R&B and even pop. Nearly all the players on the recording would go on to reinvent themselves and the music by forming bands that would define jazz fusion, most notably Joe Zawinul and Wayne Shorter with Weather Report, Chick Corea and Lenny White with Return to Forever and John McLaughlin with the Mahavishnu Orchestra. Aptly, they would bring rock audiences to jazz and revitalize the music. Stories from the recording sessions for this groundbreaking album abound and many are captured in Paul Tingen’s excellent book, Miles Beyond.

Jean Pierre (2022 Remaster) (Live at Shinjuku Nishi-Guchi Hiroba, Tokyo, Japan - Oct. 1981 -...

We Want Miles (1982)
Most of the material on this two-LP set was recorded at a performance at the Kix club in Boston with his working band at that time—Bill Evans (saxophone), Mike Stern (guitar), Marcus Miller (bass), Al Foster (drums) and Minu Cinelu (percussion). It was Miles’ first live performance in five years. This same group later appeared on Saturday Night Live where they performed “Jean-Pierre” with its signature sing-songy riff that would be quoted (and quoted again) by jazz and fusion players for the next 40 years. The double album has a loose jamming quality and contains just six tracks, with multiple versions of “Jean-Pierre,” plus “Back Seat Betty,” “Aida,” “Kix” and “My Man’s Gone Now” which he had originally recorded on the 1958 album Porgy and Bess. Although Miles was not in good health at the time, jazz fans were just happy to see and hear him play after a long hiatus. Ironically, despite not being in the greatest playing shape, Miles won a Grammy for the Best Instrumental Jazz Solo.


Tutu (1986)
At the time this album was recorded, Miles had become obsessed with the ‘80s sound popularized on MTV. He had started to record an album with Vincent Wilburn, Jr., Ray Parker and other players from the Chicago scene. But that recording was shelved for this project produced by Marcus Miller who told me that this distinctive and powerful album was very special to him. “It was my first time sitting shoulder to shoulder with Miles and working on music that I had written for him,” Miller explained. “I had been in his band for a couple years, but this was a completely different kind of relationship and a lot of responsibility. When it was released, it was the first time for a lot of people hearing that sound, which is very familiar now, but it was a different thing at the time. You can’t recreate your first time, so, yes, this one does stand out for me.” Named for Bishop Desmond Tutu, the recording has a large sound that is both of its time and of its own time. Miller said the music reflected the intergenerational relationship between Miles and him. “It was me and Miles and all his history, how was he functioning in the modern world, which was the ’80s at that time,” Miller said. “To me, it was about Miles carrying his history forward to the ’80s and to the streets of New York in that environment.” Miles would play material from this album for the remainder of his life.


In preparation for this piece, we asked WBGO followers on Twitter and Facebook to tell us their favorite Miles album and the results were as diverse as one might expect given the breadth and depth of his catalog. Many complained that it was impossible to pick one. As one listener said, “That’s like selecting a favorite food off a 5-star menu.” All of the above albums except Workin’ and We Want Miles were mentioned, and many, like the seminal Kind of Blue, E.S.P. and Bitches Brew recordings, were chosen more than once.

Here are some of the additional Miles Davis albums that WBGO listeners recommended:

Dig (1956)

Bags Groove (1957)

Birth of the Cool (1957)

Elevator to the Gallows (1958)

Porgy and Bess (1959)

Someday My Prince Will Come (1961)

My Funny Valentine (1965)

Live in Berlin (1965)

Four and More (1966)

Miles Smiles (1967)

Sorcerer (1967)

Nefertiti (1968)

Filles de Kilimanjaro (1968)

Tribute to Jack Johnson (1971)

Live Evil (1971)

On the Corner (1972)

Get Up With It (1974)

Live at the Plugged Nickel (1976)

Decoy (1984)

For over 27 years, Lee Mergner served as an editor and publisher of JazzTimes until his resignation in January 2018. Thereafter, Mergner continued to regularly contribute features, profiles and interviews to the publication as a contributing editor for the next 4+ years. JazzTimes, which has won numerous ASCAP-Deems Taylor awards for music journalism, was founded in 1970 and was described by the All Music Guide, as “arguably the finest jazz magazine in the world.”