Jazz Guitarist Jack Grassel said once he was working with a Cellist from the Milwaukee Symphony Orchestra when a person walked up and commented “Wow, your Cello sounds fantastic this evening”. Surprised at this comment the Cellist bent down and put his ear to his Cello ….”Funny” he said, “I don’t hear anything”.
We could comment that if Wes Montgomery came into a Guitar store and started playing guitars and amplifiers, everything he played would sound just like Wes. Not surprising. The artists we admire create the sound we love mostly through technique. They adjust their technique depending on the situation and equipment to get that same sound and effect. It is worthy to note that this finely honed technique took years and years of painstaking development and refinement.
Now it is true that some guitars will tend to sound darker and/or brighter which could help an aspiring musician emulate the elusive sound in question. Even Wes would have a tough time getting his sound playing a Telecaster on the bridge pickup through a Hot Rod Deluxe amplifier. But for the most part, Wes could get his sound through a variety of quality archtops or even a semi hollow body connected to a non distorting jazz amplifier.The most important choices for guitar selection should involve getting a guitar that is comfortable for you to play and that will perform well in your scenario. See “Which Archtop Guitar Is Right For Me”.