Jazz Icon | Wes’ Insight

Why Wes Montgomery Still Matters

Wes Montgomery didn’t just influence jazz guitar — he redefined how the guitar sings.

His sound was never about scales, patterns, or speed.

It was built on voice-leading, melodic symmetry, and a unique form of

diagonal movement across the fretboard that shaped every line he played.

Many players imitate the octaves.

Few understand the logic underneath.

This page brings you into that logic.

What You’ll Learn in Wes’ Insight

A clear, practical breakdown of the structural ideas that defined Wes’s signature sound:

1. The Octave Position System

How Wes used octaves not as a trick, but as a harmonic “frame” for melodic storytelling.

2. The Wes Line (ii sound)

The diagonal movement that creates the m7 quality — Wes’s foundation for building melodic motion.

3. The Hidden Reverse Line (V7 sound)

The other side of Wes’s diagonal logic, revealing how he naturally created V7 tension during ii–V phrases.

4. Diagonal Voice-Leading

How melody, bass line, and harmony connect into one flowing idea— no scales, no memorized patterns.

5. How Django Reinhardt Influenced Wes

Discover the surprising connection between Django’s two-finger shapes and the diagonal geometry that Wes absorbed and expanded.

Why This Matters For Your Playing

Understanding Wes’s diagonal logic transforms your improvisation:

  • Your lines sound connected, not random

  • Your ii–V–I becomes melodic, not mechanical

  • Your fretboard stops feeling vertical and starts feeling musical

  • You stop chasing patterns and start creating voice-led sentences

This is not a transcription site.

This is interpretation, logic, and application.

Who This Is For

This page is designed for guitarists who:

  • Are tired of scale-based improvisation

  • Want to understand the actual logic behind legendary jazz lines

  • Learn better through structure, voice-leading, and harmonic storytelling

  • Want a clear, modern way to approach jazz phrasing

If you resonate with these,

Wes’ Insight is your next step.

Wes didn’t just play notes.

He played the shape of harmony itself.

Now you can too.

Jazz Icon Series - Wes’ Insight

Wes Montgomery’s sound wasn’t built on scales—it was shaped by melodic flow, voice-leading, and diagonal movement (Wes & Django Line) across the fretboard.

This section breaks down the core principles behind his iconic phrasing and turns them into clear, practical ideas you can apply to your own playing.

Fly Me To The Moon (C)
$19.00
One time

A complete study of Wes Montgomery’s iconic approach to “Fly Me to the Moon.” This pack includes a full chord-melody of Junewon Choi, a 1-chorus solo transcription of Wes Montgomery, and a clear 10–15 minute breakdown explaining the melodic flow, thumb articulation, diagonal phrasing, and harmonic movement that create Wes’s unmistakable sound.


✓ Full PDF (Standard notation + TAB)
✓ Complete chord-melody arrangement
✓ Full solo chorus transcription
✓ 10–15 min breakdown video
✓ Analysis of guide tones, voice-leading, and thumb phrasing
All The Things You Are (Ab)
$19.00
One time

One of the most sophisticated jazz standards, interpreted through Wes Montgomery’s harmonic logic. This pack reveals diagonal movement, triad superimposition, and Wes’s ability to glide through modulations with total smoothness.


✓ Complete PDF (notation + TAB)
✓ Wes-style chord-melody arrangement
✓ Full 1-chorus solo transcription
✓ 10–15 minute breakdown focusing on harmonic flow
✓ Detailed analysis diagonal scale paths
Jazz Icon | Wes' Insight Bundle 1
$59.00
One time

Study three iconic standards through Wes Montgomery’s sound. Fly Me to the Moon reveals his smooth diagonal phrasing and melodic thumb lines. All the Things You Are shows how Wes navigates modulations with effortless voice-leading. Autumn Leaves is a rare, Wes recording from radio live—shared directly with me by Richie Hart and unavailable anywhere online—one chorus of his solo transcribed and reconstructed for this bundle only.


✓ Build Wes-style phrasing across 3 harmonic environments
✓ Understand how the same concepts appear in every tune
✓ Internalize diagonal pathways through repetition
✓ Perfect bridge between Essential → Bridge → Applied tiers