Miles Behind

My brother and I were chatting about Miles Davis yesterday. I told him (my brother, not Miles) that if he ever finds a good copy of Miles Smiles on vinyl, he should buy it for me. I think I also told him I’d pay one million dollars for it.

Part of the conversation revolved around the question of how much we truly know Miles. The dude invented, reinvented, and re-reinvented music so many times that, if you’re like me, you might know only a fraction of his actual body of work.

Lately I can’t get enough of the Hancock/Shorter/Carter/Williams group that Miles fronted for a few years in the mid-60s. Listening to this music is like arriving on the surface of some new planet. The planet resembles earth in the way that dreams resemble waking life: much is the same, but you’re fully aware that actually nothing is the same, that reality is defined on rickety terms, that the tectonic plates beneath you are actually paper plates and your lunch is a symbol for some cosmic mystery that will only make sense while the dream is happening.

I found my way into this rabbit hole through my love of Herbie Hancock and Wayne Shorter. If I were to keep listening statistics, I’d find that the middle part of 2025 was dominated by Maiden Voyage, Empyrean Isles, Night Dreamer, Juju, and, of course, Speak No Evil. That rabbit hole had an exit ramp clearly marked MILES DAVIS / SECOND GREAT QUINTET / EXIT HERE, and while I never fully exited the Herbie/Shorter highway (and probably never will), I added Miles to the route. (Thank you, ladies and gentlemen, for even daring to read the preceding paragraph, which featured the most tortured and bizarre mixed metaphor of the century.)

Which brings me back to the main point: I’ve read books about Miles and spent countless hours listening to his music, but these are records I’d never truly listened to. (Sidenote: In the 1990s I owned a CD of cuts from the famous 1965 Plugged Nickel gigs. These were years when I was trying to listen to jazz more, trying to understand it more, trying to embrace it. I wanted to like it more than I actually did like it, an impulse we should talk about eventually because I think it’s important and valuable and maybe the only reason I am the way I am. Anyway, I bought that CD probably because I liked the cover. The joke was very much on me: if you know those recordings at all, you know that they are no place for a greenhorn. Legend has it Miles didn’t even want to release those recordings in the U.S. because he sensed American audiences weren’t ready. And while I can’t speak for American audiences, I can tell you that my 1990s ears were absolutely not ready for that music. I listened diligently, trying desperately to find my place in the song structures or the meter, looking for any kind of foothold on the sheer flaming cliff of those gigs. I’d dig my fingers into tiny holes and duck while other listeners fell to their fiery deaths all around me. I watched them fall and hung on for dear life. Harrowing stuff. More mixed metaphors. Etcetera, etcetera. In case someone resembling me circa 1990s is reading this, don’t start with the Plugged Nickel recordings. They will kill you.

Start with Miles Smiles.

Miles Smiles is the record from this period that most resonates with me, though I can say I love Nefertiti and Sorcerer almost as much and fully expect to embrace E.S.P., Miles in the Sky, and Filles de Kilimanjaro once I spend time with them. After I offered my brother one million dollars for a vinyl copy of Miles Smiles, he listened to it, and eight hours later he said he hadn’t stopped listening to it. I can relate. The deeper into it you get, the more you might never want to get out. It’s beautifully sequenced, a path where a luminous and mysterious gift awaits you around every corner. Its cover tells you a lot; not so much the picture of Miles smiling (which Miles must have hated), but the color and the typography. Red and orange dominate the field; even the picture of Miles is brushed with fire. And those weird, surreal, drop-shadowed letters spelling out the title. The whole thing is incongruous in the extreme. The smile, the scorched color scheme, the insane cropping of the photo, the weird carnival letters. And yet that’s a perfect preface to what you’re about to hear. Beyond having a tremendous amount of heat, the music has a demented sense of humor, a sardonic, almost violent disregard for all things known, all things expected. Yet, before I get too carried away, let me dial it back and say part of the genius here is that you will largely understand what’s happening. This is not free jazz. This is not Ornette Coleman or even Eric Dolphy; these are tunes, and tuneful ones at that! This is more like people using conventional tools to build something way beyond the scope of said tools. If I were smarter about art, I’d say this is like Dali or maybe Picasso (hell, or maybe Hemingway), a creation that’s all about recognizable objects shaped into new and exciting forms. (You’ll have to forgive me; I asked ChatGPT to talk to me about modernism yesterday, and I think maybe I’m still buzzing from that exchange.)

I have my brother in mind as I write this, and I could see him reading that last paragraph and vomiting. As a response to his fully justified vomit, let me say this: you could also just listen to Miles Smiles and think, wow, got damn, these dudes are seriously badass.

King of the badasses here might be the 20-year-old Tony Williams. Let’s just say I’m not an especially religious guy, but I’d consider going to a church organized around worshipping his ride cymbal. His ride cymbal is the blue flame beneath the simmering stew of this band. He is the catalyst, the heat, the source, the wizard fueling the alchemy. Listen to “Footprints.” Williams isn’t just changing the meter, he’s slipping from one dimension into another, finding permeable surfaces and gelatinous substrates where other drummers see only right angles and brick walls.

My brother complained about the piano sound on this record, and I have to agree, though I need to point out the complexity of the issue. Weirdly, you don’t hear Herbie at all until you’re almost three minutes into the first track, “Orbits.” For that reason alone, the piano sounds kind of foreign and unwelcome right off the bat. Apparently this was no accident. Some annoying jazz genius can correct me on the specifics here, but my understanding is: A) Miles didn’t want Herbie to play a lot outside of his solos because he didn’t want the piano adding all that harmonic content to the music. This in itself is radical and brilliant and part of why this record keeps me coming back; there’s a harmonic ambiguity that makes these songs more powerful and sneaky and beguiling. It’s the power of subtraction in art. B) Herbie says in his autobiography that around the time of this record Miles told him, “Stop playing the butter notes.” Herbie wasn’t sure he even heard Miles correctly, but he took it to mean he shouldn’t play the big fat obvious notes. This resulted in Herbie seriously limiting the use of his left hand while playing, so that, again, he was contributing less harmony and thinking more in lines of single notes. When Herbie comes in for his solo on “Orbits,” all of this contributes to the overall effect. (Also, more to my brother’s point, the piano tone at times leaves something to be desired, coming across as a little artificial and sonically clumsy; my brother said it sounds like the piano setting on a cheap keyboard. Whether this is down to the piano itself or the way it was mic’ed and recorded, who knows. For most of the record it actually sounds great to me, but there are spots where it’s a little jarring, not totally mixed into the sound of the rest of the band. I look forward to finding out whether the piano sounds more organic on vinyl, and you better believe I’ll be hitting up ChatGPT for more info on this topic.

Sidenote: ChatGPT must think I’m a really special case; all we ever talk about is jazz (e.g., “Talk to me about Herbie’s piano tone on Miles Smiles; it sounds kind of plastic-y sometimes, right?”) or how to brew the perfect cup of coffee (e.g., the acidity on this honey processed Colombian from Wonderstate is a little bitter? Or maybe sour? I must have used too fine a grind, don’t you think? Or maybe the water should have been 201 degrees instead of 202?)

I listened to a podcast recently where someone—a physicist, I think—challenged the (apocryphally attributed to Einstein) idea that insanity is defined by doing the same thing over and over and expecting different results. He calmly pointed out that, in fact, we frequently do the same thing over and over and get totally different results. His example was some kind of neutron laboratory where they would recreate the exact same sequence of atomic events and, in fact, get different outcomes every time. This blew my socks off. My wife laughs at me for reading the same books over and over again, but I stand by it, and the anecdote above is why. I return to certain works over and over again exactly because I get different—and better—results. Miles Smiles is the ideal record for this mindset. It is a jewel with countless surfaces, forever refracting diaphanous light. Every time you look, you see something different, something even more enchanting than what you saw last time. And when you think you’ve got it figured out, believe me, you do not.