A Beginner’s Guide to Miles Davis

Inspired by: A beginner’s guide to modern art jazz

Miles Davis (1926-1991) was a jazz trumpeter, bandleader, and composer. He was one of the most influential figures in the history of jazz, and he had a prolific output (just on Spotify, he has over 1,000 songs). Many of these are different recordings of the same song, but jazz is so improvisational that it’s difficult to draw the line of what counts as a distinct song.

My aim with this guide is to write something that would have been very helpful to me when I started listening to Miles Davis. I will list and discuss the albums that I view as essential listening, and bullets beneath will list my favourite songs from that album. This list is far from comprehensive and there are many albums I chose to leave out. This means that the jazz fusion period is underrepresented, because I personally don’t like it as much as his earlier work. Miles was famously difficult, rude, and beat his wives on multiple occasions. So do not take this piece as an endorsement of him as a person. If you feel that I missed something important, please don’t hesitate to contact me.

This post is grouped chronologically within periods, but the different periods overlap so it’s not strictly chronological. Some of the years in this post may be confusing because of the lag between recording and release. The years I mention are from the date of release. This difference is most apparent for Cookin’, Relaxin’, Workin’ and Steamin’ with the Miles Davis Quintet, all of which were recorded over a two-day session in 1956 (!) to complete Davis’ contract with Prestige records.

There is a perception that jazz is dead, and Davis himself even famously declared that jazz was dead. This is pretty unfair. For one thing, almost all of jazz is on Spotify now at amazingly high quality. For another, the decline of the cultural centrality to jazz has led to a decline in the price of concert tickets, etc., such that there’s high returns to having expertise. Tyler Cowen writes that “current times are the very best for jazz, ever”.

Jazz is so interesting to me because of its fusion of intricate underlying structure with improvisation and spontaneity. As Ken Burns put it, jazz is “familiar, but brand new every night”. Moreover, I enjoy the intellectual demandingness of jazz as a genre. Jazz musicians seem to be the most thoughtful and intelligent of any genre. Many of the more Avant Garde songs mentioned in this post don’t sound good unless you’re really concentrating. Some of it sounds cacophonous to a newcomer. This is why jazz is considerably more difficult to get into than other genres and has a lack of listenership among the youth.

Disclaimer: I’m a philistine with limited musical knowledge or ability. This guide is by no means meant to be authoritative. But I worked very hard on it. So, after hundreds of hours of listening, I present to you: a beginner’s guide to Miles Davis. You may find this guide significantly more helpful if you follow along with this playlist on Spotify, which compiles all of the featured songs in order.

The Early Years (recorded pre-1955)

Miles Davis’ career spanned the most important eras in jazz. He replaced Dizzy Gillespie as trumpeter for the quintet of the legendary saxophonist Charlie Parker, which is how he first came to notoriety. There’s a lot of static on the earlier recordings. This doesn’t bother me so much anymore, but in any case, I recommend remastered versions where you can find them. My overall highlights from this era are Boplicity, Four, and Bags’ Groove.

The Musings of Miles (1955)

  • Will You Still Be Mine
  • Green Haze
  • A Night in Tunisia

Blue Haze (1956)

  • Blue Haze
  • Four
  • That Old Devil Moon

Collectors’ Items (1956)

  • In Your Own Sweet Way
  • Compulsion

In general, there are many remastered, extended and reissued versions of all of Davis’ popular songs and albums, and frequently no canonical version. Luke Muehlhauser talked about this on his blog, which I recommend.

Bags’ Groove (1957)

  • Bags’ Groove
  • But Not for Me
  • Doxy

If you listen to this album, it’ll probably be the Rudy Van Gelder (RVG) remaster. Van Gelder was a legendary audio engineer known for editing in such a way that produced a distinctive sound.

Birth of The Cool (1957)

  • Boplicity
  • Move
  • Israel
  • Moon Dreams

As far as I know, this album played an important part in the etymology of the word cool. Davis, with his suits, beautiful women, and suave look, was the definition of cool. He was part of what it meant to be cool. In his later more experimental years his clothing was much more unusual, colourful, and counter-cultural. Another interesting thing about this album is how Davis exemplified a kind of 50s masculinity, but his music was disarming and romantic. It was very common for couples to go to see him in jazz clubs together.

Miles Davis and the Modern Jazz Giants (1959)

  • ‘Round Midnight
  • The Man I Love
  • Bemsha Swing

The First Great Quintet (1955-59)

Miles Davis’ band repeatedly shifted in its composition, but it can be roughly grouped into two stable periods: the First Great Quintet and the Second Great Quintet. There is a famous debate among Miles Davis fans over which quintet is better. The First Quintet had Red Garland on piano, Paul Chambers on bass, Philly Joe Jones on drums, and John Coltrane on tenor sax. Cannonball Adderley later joined with alto saxophone (making it a sextet). Davis had a reputation for featuring up-and-coming unknown artists on his album, and he launched Coltrane’s career. If you are only vaguely familiar with Davis sound, it’s likely this is the period that you recognise. It includes Kind of Blue, the best-selling jazz album of all it. Bill Evans replaced Red Garland on piano for some of this period, most famously on Kind of Blue. My overall highlights from this era are ‘Round Midnight, Walkin’, Milestones, My Funny Valentine and So What.

‘Round About Midnight (1957)

  • ‘Round Midnight
  • Bye Bye Blackbird
  • Ah-Leu-Cha
  • All of You
  • Dear Old Stockholm

‘Round Midnight by Thelonious Monk is one of the most famous jazz standards. Miles was the origin of many jazz standards, including Milestones and So What.

Walkin’ (1957)

  • Walkin’
  • Solar
  • You Don’t Know What Love Is

In general, title tracks really are better on average.

Cookin’ with the Miles Davis Quintet (1957)

  • My Funny Valentine
  • Airegin
  • Blues by Five

Milestones (1958)

  • Milestones
  • Straight, No Chaser
  • Two Bass Hit
  • Billy Boy

One interesting feature of jazz is that it’s a fundamentally American genre. American songs dominate popular music, and especially so with jazz. Some of this is because of the specific role played by race relations in jazz history. But one could speculate that there’s a deeper reason. America, at its best, has separation of powers and constitutional protections (or, rather, it has a longer history of this than other developed countries). It’s all about error-correction and human fallibility. Jazz, likewise, is all about revising and improvising. Contrast this with continental Europe, which has spent much of its history falling prey to one utopian ideology or another, with classical as the dominant music of high culture.

Relaxin’ with the Miles Davis Quintet (1958)

  • It Could Happen to You
  • If I Were a Bell
  • I Could Write a Book

It’s worth mentioning that the mid-to-late 50s was the apex of Davis’ cool jazz period. This is much lower tempo than bebop, which is characterised by fast continuous saxophone melodies and is where Davis got his start. Cool jazz is what people might think of as ‘coffee table jazz’. I sometimes work while listening to it, but other sub-genres within jazz are too fast-paced and complex for me to listen to while concentrating on something else. Some jazz purists would disdain the idea of listening to jazz while working at all, as opposed to giving it your full attention. Indeed, before maybe a year ago, I had never intensely listened to music while doing nothing else for any significant period, because I got bored too easily. But now I usually listen to jazz while browsing the album covers, and very often with my eyes closed.

Kind of Blue (1959)

  • So What
  • Freddie Freeloader
  • Blue in Green
  • All Blues
  • Flamenco Sketches
  • On Green Dolphin Street
  • Fran-Dance
  • Stella By Starlight
  • Love for Sale
  • So What – Live at Kurhaus

This was a major force in the introduction of modal jazz, characterised by switching among musical modes. It’s essential to listen to all of it. The last few songs listed here are from the extended edition of the album. I recommend the extended versions of most of these albums, where one exists, and listening to alternate takes of the same song. Sometimes the albums also include banter from the band, in which you can hear Miles’ famously raspy voice, which he acquired because of a throat condition.

Workin’ with the Miles Davis Quintet (1960)

  • It Never Entered My Mind
  • In Your Own Sweet Way
  • Trane’s Blues

If you really liked any of the music from before this point, you’ll probably like most or almost all of it. One of the great things about jazz is that there’s a functionally infinite amount of top-tier jazz, supposing you don’t have extremely niche tastes, while with almost everything else I consume I struggle to find content I love that I haven’t already read/watched/listed to.

Steamin’ with the Miles Davis Quintet (1961)

  • When I Fall in Love
  • Salt Peanuts
  • Surrey with the Fringe On Top

Salt Peanuts has been stuck in my head a lot recently. Because jazz usually doesn’t have any vocals, it’s harder at first for songs to get stuck in your head or to tell them apart. With time, I’ve gotten a lot better at this. There are certainly excellent jazz vocalists – Ella Fitzgerald, Billie Holiday, Chet Baker. But there is something to be said for consciously choosing to not have any lyrics in your music. Asking why jazz doesn’t have any words strikes me as a bit like asking why novels don’t have any pictures. The music speaks for itself.

Someday My Prince Will Come (1961)

  • Someday My Prince Will Come (yes, it’s based on the theme from Snow White)
  • I Thought About You
  • Old Folks
  • Teo

This may be my favourite album cover of all time. In general, the album covers from the golden era of jazz are absolutely gorgeous. This seems like a lost art because album covers are so much less prominent in the digital era. The Sketches of Spain, Miles Ahead, and Birth of the Cool covers are all iconic. I think that one of the first things that drew me to jazz, before I had any appreciation for the music, was the way people looked when they were playing it. They just looked so cool!

Collaboration with Gil Evans (1957-63)

Davis’ collaboration with the pianist and arranger Gil Evans was legendary. My overall highlights are Miles Ahead, The Duke, Summertime, and Solea.

Miles Ahead (1957)

  • Miles Ahead
  • The Duke
  • Blues for Pablo
  • New Rhumba

Another point: this is not dancing music. I believe that some of Davis’ concerts even had signs up to stop people from dancing. This is in stark contrast to earlier years of jazz, which developed around a culture of dancing halls and highly rhythmic music. Take this with a grain of salt, but it seems like one of the motivations for this era of jazz was to prove to white people that black people were capable of inventing a rich and complex art form that was musically on a par with classical. Indeed, Lee Morgan, the jazz trumpeter, famously said that jazz should be called “black classical music”.

Porgy and Bess (1959)

  • Summertime
  • It Ain’t Necessarily So
  • Buzzard Song

Porgy and Bess is a famous opera by George Gershwin. The Gershwin songbook has been covered many times, and the rendition by Louis Armstrong and Ella Fitzgerald might be the most famous. There have been more arrangements of summertime than anyone can keep track of, but I think Davis’ may well be the best.

Sketches of Spain (1960)

  • Solea
  • Will O’ The Wisp
  • Concierto de Aranjuez: Adiagio
  • The Pan Piper

This album was inspired by his wife, Frances Taylor Davis, and her love of flamenco dancing. Sketches appears to be his first movement toward an acoustic-electric sound. I was surprised to learn that this album is somewhat controversial among Davis fans, so I think it’s thoroughly underrated.

The Second Great Quintet (1964-68)

Miles Davis’ Second Great Quartet had Herbie Hancock on piano, Ron Carter on bass, Tony Williams on drums, and Wayne Shorter on tenor saxophone. Its sound was more unconventional, and arguably the 60s are passed the ‘golden era’ of jazz. E.S.P. and Seven Steps to Heaven are my favourite albums from this era. My overall highlights are Seven Steps to Heaven, E.S.P. and Agitation.   

Seven Steps to Heaven (1963)

  • Seven Steps to Heaven
  • I Fall in Love Too Easily
  • Basin Street Blues

One of my favourite things about jazz is the extent to which its subject matter is universal. Many (most?) popular songs are about love, which is fine, but it’s narrow. The best jazz is a kind of philosophical meditation about the tension between planning and improvisation. The benefits of bottom-up versus top-down design. The extent to which life is an interrelated mesh of trade-offs and constraints. How beauty – and perfection –balances on a knife-edge between order and chaos.

E.S.P (1965)

  • E.S.P.
  • Agitation
  • Mood

I don’t have the musical talent to predict which way a piece of jazz will go, but there is a very satisfying way in which it feels like the notes makes sense after they’re played. It’s curious: I feel like asking ‘how could it have been otherwise?’, when of course, it could easily have been otherwise.

Miles Smiles (1967)

  • Footprints
  • Circle

Bill Evans, who was a pianist with the Miles Davis Quintet for a time, once said “There are no wrong notes, only wrong resolutions.” The way the very same note can sound totally different when played accidentally by an amateur compared to consciously played by a virtuoso is fascinating to me.

Nefertiti (1968)

  • Nefertiti
  • Pinocchio

Nefertiti is one of Davis’ last albums of ‘conventional’ jazz before he developed a more experimental style.

The Fusion Period (1968-91)

One of the key things to understand about Miles Davis is the extent to which he was continuously switching up his style and changing genres. Jazz fusion and Avant Garde jazz are acquired tastes. I found Directions to make for the easiest listening. My favourite songs from this section are Love for Sale, Duran and Black Satin.

Filles De Kilimanjaro (1968)

  • Filles de Kilimanjaro
  • Frelon Brun

The trumpeter Wynton Marsalis once said that “in jazz, every moment is a crisis.” This was a much more elegant way of putting one of my earlier points about the universality of the themes in jazz.

In a Silent Way (1969)

  • Shhh / Peaceful
  • In a Silent Way

Bitches Brew (1970)

  • Bitches Brew
  • Pharaoh’s Dance
  • Miles Runs the Voodoo Down

Perhaps the most famous jazz fusion album of all time. There are single versions and shorter edits of many of these songs, which you might appreciate if you don’t like listening to long songs. Many of his fusion pieces are 30+ minutes long.

A Tribute to Jack Johnson (1971)

  • Yesternow
  • Right Off

On the Corner (1972)

  • On the Corner
  • Black Satin

Miles took a lot of inspiration from world music, as evidenced in Sketches. This album uses a lot of Indian percussion.

Circle in the Round (1979)

  • Circle in the Round
  • Love for Sale
  • Two Bass Hit

Placing this in the fusion period is somewhat of a mischaracterisation, because this album compiles 15 years’ worth of previously unreleased tracks. Nonetheless, the title track is the first recording where Davis used electric instruments.

Directions (1981)

  • Directions I
  • Directions II
  • Duran
  • Water on the Pond

Tutu (1986)

  • Tutu
  • Time after time – live in Nice (from the Deluxe edition)

Davis continued making music until he died in 1991, but the most recent material is of more mixed quality and never really found an audience. Some of the live recordings from this period are much better, however, as we’ll see in the next section.

Live Recordings and Soundtracks

I actually prefer listening to live recordings. They often last much longer than the originals and they give interesting re-imaginings and re-interpretations of familiar tracks. My favourite songs in this section are So What, Walkin’, Générique, Sur l’autoroute and Autumn Leaves.

Ascenseur pour l’échafaud (1958)

  • Générique
  • Sur l’autoroute
  • Florence sur les Champs-Élysées
  • Dîner au motel

This album was an improvised soundtrack for a French film. After spending some time in France in the 50s, Davis was frustrated when he returned to America’s more backward racial attitudes. It’s possible that this anger influenced his music, but I really don’t know.

The Complete Live at the Plugged Nickel (1965)

  • If I Were a Bell
  • Stella by Starlight
  • Yesterdays
  • My Funny Valentine
  • I Thought About You

One of the themes I find most interesting in jazz is the constant tension between improvisation and planning. The different takes sound really different to one another. You would naively think that, however good your music is when you’re composing on the spot, it must be better when you can plan it out in advance. But something is lost when you write the music down. In the very early days of jazz, even the introduction of recording technology was controversial, because when you can record music there is a sense in which it becomes set in stone, and unchanging. But jazz, it was argued, was all about change and revisions. There’s an obvious parallel here with Socrates’ dislike of writing. I say “on the spot” but this is unfair: jazz improvisation requires tremendous practice and intellectual effort. People sometimes conflate “genius” with “very talented”, but so far as I’m concerned, Miles Davis was legitimately a genius in this regard.

“Four” & More (1966)

  • Four
  • So What (this is my favourite take on the song)
  • Joshua
  • Walkin’
  • There is No Greater Love

Stockholm 1960 Complete (1992)

  • Stardust
  • Lover Man
  • Makin’ Whopee
  • Autumn Leaves

Side note: It’s striking how many errors are made in the transcription of lesser-known albums onto Spotify. A lot of the songs on this album have inconsistent capitalisation, i’s that aren’t capitalised, and others have spelling errors.

Miles and Quincy Live at Montreux (1993)

  • Solea
  • Boplicity
  • The Duke
  • Summertime
  • Springsville

This was recorded the year that Davis died, with Quincy Jones. You can tell that he had lost some of his technical proficiency with the trumpet by this point. While Davis was at a time extremely fit and enjoyed boxing, decades of frequent alcohol, cocaine, and heroin use took its toll. With Davis, though, you’re generally not listening for technical proficiency: he certainly couldn’t play faster or higher than some other trumpeters. It’s more that his style is incredibly distinctive. Even today, I’m not aware of any trumpeter that can make their instrument sound the same way Miles could, which is an impressive feat for any musician.  

Bonus: Books, documentaries and films about Miles Davis I recommend

Miles: The Autobiography

Miles Davis wrote an autobiography with Quincy Troupe, which understandably is essential reading for understanding him.

Jazz (Ken Burns)

This is a documentary series and accompanying book. I haven’t been able to find a place to affordably watch the documentary, but I recommend the book wholeheartedly. I also recommend this YouTube interview with Wynton Marsalis and Ken Burns about the series. A quote I liked: “When historians in 1,000 years look back on America, it’ll be remembered for three things: baseball, the constitution, and jazz.”

Miles Ahead

This film is set during Davis’ dormant period in the late 70s in which he was struggling with drug addiction and not making any music. It’s pretty good, though not amazing. The film was Don Cheadle’s directorial debut and stars Don Cheadle and Obi-Wan Kenobi Ewan McGregor. Cheadle did a great job with the raspy voice. People who know about this sort of thing say that the fingering and playing look believable because Cheadle actually learned how to play trumpet for the film.

The film was scored by the excellent Robert Glasper, who also produced the ending track, which is really good. I’ve included the Go Ahead John edit from the film in the playlist. I have had frustrations trying to find jazzy hip hop where the jazz wasn’t just bad or excessively electronic. Kendrick Lamar and Glasper seem like exceptions to this. Glasper also made a video for Wired where he reviewed jazz scenes in films, which you should watch.  

Miles Davis: Birth of the Cool

One of my favourite documentaries. It contains interviews with Herbie Hancock, Wayne Shorter, Frances Taylor Davis, and others. They even interviewed the French woman whom Davis had a relationship while he was living in Paris in the 50s. The soundtrack is really good, and it includes Donna Lee, which I’ve also included in the companion playlist.

Other podcasts and videos

There were interesting discussions about Miles Davis on the Conversations with Tyler episodes with John McWhorter and Kareem Abdul-Jabbar (you can search the transcripts to skip to the relevant part). I’m not sure whether they mention Davis specifically, but Tyler Cowen’s discussions with the music critics Alex Ross and Ted Giola are also excellent. Giola now has a Substack that you should subscribe to if you enjoyed this post. I also enjoyed this video from the YouTube channel Polyphonic about Kind of Blue. All of his other videos about jazz are also worth watching.

Thanks to Sydney, Gytis and Tom for reviewing drafts of this piece.

9 responses to “A Beginner’s Guide to Miles Davis”

    • Hey Richard, thanks for the comment. Perhaps I didn’t make it clear enough – these are just my favourite Miles Davis albums that I think are good for a beginner to listen to. There are many albums I didn’t include, including those two, which I personally don’t like that much


      • Sam thanks for your response to my comment. I grew up listening to Miles, my father was a jazz drummer when L.A. had the Central Ave Jazz scene. However I do agree with most of your selections except Filles de Kilimanjaro couldn’t get into that one at all. Again thanks for your reply have a great day and keep listening to Miles he makes you think.


  1. > Americans songs dominate every popular genre

    Say, what?

    Electronic dance music is wildly popular everywhere except the US and is dominated by European and UK artists. Reggae and dub are dominated by Jamaican musicians, baghara by Indian musicians, dangdut by Indonesians, drum’n’bass by British and Jamaican musicians, and then we have all these African styles which are also extremely popular – outside the US, that is.

    > America, at its best, has separation of powers and constitutional protections.

    As does the majority of the developed world, yes?



    > Contrast this with continental Europe, which has spent much of its history falling prey to one utopian ideology or another, with classical as the dominant music of high culture.

    Say, what???


    • Thanks for the response. The comment I made was speculative, to be sure. I switched the wording to “America dominates popular music”, which is more what I meant.

      Jazz was very popular before and during the Second World War, when Europe… did not have those things.

      Of course, I know that most of the developed world has those things. I’m European and I have only ever travelled within Europe. I was just musing that maybe the longer history of cultural and institutional understanding of human fallibility in America compared to other places had an influence on its aesthetic and musical tastes.


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