Jamie Holroyd Guitar

Jamie Holroyd Guitar

Play Like Wes Montgomery Today

Play Like Wes Montgomery Today

Wes Montgomery is to jazz is what Jimi Hendrix was to rock and this lesson explains a few key ways that will help you play like Wes Montgomery. Hardly an obscure jazz guitarist, along with Charlie Christian and Django Wes is one of, or perhaps the greatest influence of jazz guitar.

Besides the virtuosic use of the unusual thumb right hand technique and mastery of octaves, Wes was a master of block chord soloing, earthy blues lines, jazz rhythms and he played with an unmistakable swing feel. Today’s lesson aims to improve your jazz guitar improvisation techniques by look at some aspects of Wes’ distinctive guitar style.

There’s probably not one jazz guitarist alive who hasn’t been influenced by Wes; Pat Metheny and Peter Bernstein have stated him as an influence and even his contemporaries such as Jim Hall, Pat Martino and George Benson have acknowledged him. Jim Hall once jokingly said “I once tried spent an entire evening in San Francisco trying to trap Wes’ thumb in a car door.”

While it’s no easy task for anyone to exactly play like Wes Montgomery, there are a few techniques Wes’ used that other jazz guitarists have observed over the years that I would like to share in this lesson.


The Thumb


The first thing anyone will notice when watching a video of Wes is that he plays exclusively with his thumb instead of using a pick. There are various stories about why he adopted the thumb as his main right hand technique. Some say that his wife said the music was too loud while others say it was because he lived in an apartment and had to keep the music down.

Mastering the thumb technique would take many hours of practice so most guitarists use this as a second approach because of the soft warm tone that is produced. Like any right hand technique there is no ‘set method’ and every guitarist is different but I personally like to use the fingers to anchor my hand and improve the picking accuracy as seen in the picture below.

Try improvising with the thumb on slow to medium tempo tunes at first to get used to it to play like Wes Montgomery. The thumb also works great for subtle comping behind a piano player.


play like wes montgomery




Wes certainly wasn’t the first guitarist to use octaves in a jazz setting, but he took them to a new level and frequently used them this in his solos and compositions which means they are a signature part of learning how to play like Wes Montgomery.

The two octave shapes that Wes liked to use are shown in the diagram below. The string in-between the two notes must be chocked  so that is not played. Having the muted string between the two notes produces a percussive and punchy effect.

Wes used two octave shapes but played them slightly differently. He played shape 1 using his 1st and 3rd finger, and shape 2 with his 1st finger and pinkie finger. I personally like to use the 1st finger and pinkie for both shapes, and so did Emily Remler, but experiment for yourself and use whichever feels comfortable.


play like wes octaves


Try playing a few scales and patterns to get used to switching between the two shapes. Here is how an A major scale looks played in octaves


A major octaves


Due to the technical restrictions of octaves, Wes would tend to use them for themes, strong melodic lines, and to create rhythmical interest more than for playing faster lines.

Here’s a passage from Wes’ solo on the great Jerome Kern standard ‘Yesterday’s which demonstrates how he would use octaves rhythmically by playing them in constant eighth note triplets. Here we have a D Dorian scale played in triplets. Click here to listen to the track and notice how much Wes uses triplets towards the end of his solo.


play like wes octave triplets


Here’s another example of how to use octaves rhythmically from his classic jazz guitar solo on ‘West Coast Blues’. The West Coast Blues is a classic solo because it demonstrates one of Wes common improv approach where he would build his solos by starting with single lines, moving to octaves and finishing with block chord soloing. Check out ‘Misile Blues’ and ‘Cariba’ (examined later in the lesson) for examples of this.


octave rhythms



Chord Scales


Wes was a master at using chord solos in his improvisations and a chordal technique that he is often associated with is block chords which are four note chords on the top four strings.

A popular technique that Wes used to harmonize his scales in chords was combining drop 2 chords and dominant 7b9 chords.

The chart below shows how Wes would harmonize a Minor 6th-Diminished scale by using a dominant 7b9 chord on every second note implying a strong sense of tension and resolution. The dominant 7b9 is particularly effective here, because of how well b9’s function in minor ii-V-Is. This chord-scale should be practiced in all 12 keys and applied in jazz guitar chord solos.






Call and Response


Many of Wes compositions such as Missile Blues, Jingles, and D Natural Blues were written using call and response technique which a common feature of hard bop music and players.

Wes often utilized this technique in his improvisation too, so I am going to show you two examples of how to play like Wes Montgomery using call and response in composition and improvisation.

The following example is an extract from one of Wes’ lesser note, but great compositions ‘Up and At It’ which shows how Wes would play a head in octaves and answer the melody with chords (marked out with cross note quarter notes on the sheet).

Examples of this call and response in chords can also be heard on ‘D Natural Blues’ and ‘Yesterdays’. This composition also demonstrates the 16th note that Wes often implied in his single line soloing too.


up and at it lead sheet guitar



As mentioned earlier, Wes also used the call and response technique in his single line soloing so here’s one of my favorite licks from his solo on ‘Four on Six’ from ‘Smokin’ at the Half Note’ that shows call and response. If you have the full track, it’s also worth checking out and taking note of how he carries on the motif throughout the tricky chord changes.

To practice using the call and responce technique, try playing strong melodic phrases that connect together over one chord at first before a full progression.


play like wes montgomery


Wes plays the lick around .50 in


Interchanging Chord Types


Wes’ sense of harmony was based of interchanging different chord types. My friend and the fantastic author to Wes’ bio Adrian Ingram showed me this technique in a lesson once. Interchanging chord types is a great soloing and comping technique and Wes would see one chord as being various different chord types for greater harmonic soloing potential.

This example shows how Wes liked to mix up ii and V chords on his own composition ‘Cariba’. Notice how he uses drop 2 minor 7th inversions on the top four strings over the Bb backing to create a fresh suspended modal type of sound.


play like wes montgomery


Double Picking


While I am quite sure Wes wasn’t the first to use this technique, it is one that I frequently hear him use so I think it should be part of this Play Like Wes Montgomery lesson. Wes would often double pick notes to end or begin a phrase.

He also frequently highlighted the 9th of a chord which produces a sweet and light sound which I highly associate with his sound. I have written out two licks below using different rhythms which shows how you can double pick a note starting on the 9th of a chord to get some more Wes flavour.


wes double pic

Guitars and Amps


Wes had a fanastic warm jazz guitar tone that came from his fingers, but if you are anything like me and enjoy finding out what guitars and amps players use you will find this part interesting.

Wes favoured Gibson archtops through his career and is often associated with the Gibson L-5 guitar which Gibson make a signature model of, but before 1960 played an L4 with a CC pickup, an ES-125D and an ES-175. Amp wise, most of Wes early recordings were on a Fender twin or deluxe reverb, and he switched to Standel custom solid state amps later in his career.


play like wes montgomery



Recommended Albums


  • Echoes of Indiana Avenue
  • Smokin’ at the Half Note
  • The Incredible Jazz Guitar of Wes Montgomery
  • Full House
  • A New Dynamic Sound


I hope this article on how to play like Wes Montgomery has brought some inspiration to your practice routine and helped you get some of that flavour into your lines. There’s quite a lot of things to practice here, so remember to just focus on applying one technique at once rather than trying to cram them all in.

Even though, he’s one of the most well known jazz guitarists, I still find myself coming back to listen to him every couple of months. What are some of your favorite ways to play like Wes Montgomery? Share your thoughts in the comment section below.




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Thanks Jamie for a great lesson. Lots of wonderful information and background. All the best Dave

Jamie Holroyd

Thanks Dave, glad to know you found it useful.

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Good stuff! I am having a tough time with the minor 7 chord (third chord F-7 in first bar of Carriba, for example), getting the left hand fingers on it quickly. Any advice? How do you finger it? Thanks.

Jamie Holroyd

Thanks, that chord is a tough one and there's a few ways you can play it. Joe Pass used to bar the top two strings with his secound finger, and that's how most people get to that chord quick enough, however I find that hard so I play this chord instead xx3344 which works just as well and is much easier to get to. Hope this helps.

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Jerry Boynton

I've been a fan of Wes for as long as I can remember. Thank you for dedicating a lesson to him. Very well done. Jerry

Jamie Holroyd

Thanks Jerry, glad you enjoyed it!

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So Awesome to get free lessons from one of my all time jazz-guitar-gods. Thanks so much for this....:) just phenomenal!!!

Jamie Holroyd

Thank you very much for your kind words!

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Love this lesson (and all of them really). May I ask how you to apply that Chord Scale part over say a Fma7 and a G7?

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Hi Jamie - do you have an intro to jazz book that covers how to play standards with chords and melody so you don't have to play with anyone else? Thank you so much!

Jamie Holroyd

Ho Rona, thanks for the comment. Yes I do, here is the link. Please let me know if you have anymore questions:


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Jamie! My hero!!! Excellent !!!

Jamie Holroyd

Thanks Sy, still loving the T-shirt. I hope all is well!

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