How Did Wes Montgomery Build a Solo? Single Line, Octaves, Chord Solo — One Arc on Gone with the Wind
Wes Montgomery built a solo the way a composer builds a piece: single-note line first, then octaves, then a full chord solo, then back down to chord melody to close. That three-layer arc — not the thumb, not the octave shape by itself — is the real Wes Montgomery guitar technique, and you only learn it by transcribing an entire performance, chord solo included. At VoiceLid Jazz Guitar, the online jazz guitar lessons I teach treat Wes as a structural thinker, not a collection of licks. I'm Junewon Choi, a Berklee-trained jazz guitarist, and the first tune I ever transcribed front to back under my teacher Richie Hart was Wes's Gone with the Wind from The Incredible Jazz Guitar of Wes Montgomery. Twenty years later I can still sing every chorus. Here's why that one solo teaches more than a hundred phrases.
What does the arc actually look like?
Put the record on and follow the shape:
Melody — stated cleanly, in Wes's register, already voice-led.
Single-line solo — Wes Lines and Django Lines connecting the 3rds, one position at a time.
Octave solo — the same lines, doubled, which changes the rhythm because the thumb can't fit as many notes.
Chord solo — the melody's guide-tone skeleton fully harmonized on top, block chords moving by voice leading.
Chord melody out — a return to the tune, now with everything you just heard folded into it.
From the first note to the last, Wes is the protagonist. Nothing is filler. Each layer is the previous one with more voices added.
Why transcribe the chord solo, not just the lines?
Because the chord solo is where the logic is visible. A single-note line can hide its skeleton; a chord solo can't. When you transcribe Wes's block chords on Gone with the Wind, you find that the top voice is a melodic line targeting the 3rd of each chord, and the voices underneath are guide tones moving by step — the same thing his single-line chorus was doing, now with the harmony shown. That's why Richie Hart made me learn every note of it, one at a time: the chord solo is the answer key to the line solo. Skip it and you've learned Wes's vocabulary while missing his grammar. If you want to go deeper on exactly that grammar, Wes' Insight breaks down the fretboard logic behind the lines and the octaves as one system.
How is this different from copying a Wes lick?
A lick is one bar pulled out of a story. The arc is the story. When you transcribe the whole thing, you learn things a lick can't give you:
Pacing — how long Wes stays in single lines before he lets the octaves in
Register — where the octaves sit so the chord solo has somewhere to go
Voice leading across layers — the same 3rd-to-3rd motion in the line, the octaves, and the chords
Time feel — because you copied the whole chorus, not a phrase, you inherit his placement against the beat
How to end — the return to chord melody is a composed ending, not a fade
Most players who "sound like Wes" have the octave technique and none of the rest. The rest is what makes it music.
Why could Wes say he never practiced?
Because his ear did the practicing. Wes famously answered "practice? No — I play" and he meant it: he could hear an orchestra and pick out the one line he wanted, he grew up in a musical household, and he learned songs completely by ear. So when he touched the guitar he was reproducing something already heard. That's not permission for you to stop practicing. It's a description of the goal: hear the whole arc so clearly that playing it is just recall. Transcribing Gone with the Wind end to end is the closest a mortal gets to that. I'm going back to redo it this year, because I did it too early the first time and now I can hear more.
How do I start this transcription without drowning?
Take it in the same layers Wes built it. Melody first, until you can sing it. Then the single-line chorus, slowly, keeping the position Wes used rather than the one that's easiest — on guitar the same note lives in six places and the position is the content. Then the octaves. Then the chord solo, one voice at a time from the top down. For why most Wes transcriptions you find online sound wrong when you play them, read Why Do Wes Montgomery Transcriptions Sound Wrong When You Play Them?. And for the deeper point — that the chord solo and the line solo are the same system — see Chord Melody and Soloing Are the Same Thing.
The short version: don't learn Wes's phrases. Learn one of his arcs.
If you want the diagonal system Wes's lines and chords both live on, from the ground up, Fundamental 1: Wes Diagonal System at https://www.voicelidjazzguitar.com/fundamental-1-wes-diagonal-system is where the FDA starts.
About the Author
Junewon Choi is a Berklee-trained jazz guitarist and the founder of VoiceLid Jazz Guitar, an online education platform teaching jazz harmony and improvisation through the Functional Diagonal Approach (FDA) — a chord-first method built on voice-leading rather than scale boxes.
Wes' Insight — Wes Montgomery's fretboard logic, in lesson form
Fundamental 1: Wes Diagonal System — the FDA from the ground up