Besides being a great song, Willie’s guitar solo in this performance is constructed just about perfectly. My parents are big fans of Willie Nelson, so I heard a lot of his music growing up. Until relatively recently, I had overlooked Willie as a guitar player — an unfortunate oversight on my part.
The man has a truly unique sound and style that perfectly complements his vocal approach. Part of that uniqueness comes from his number one instrument, Trigger (a 1969 Martin N-20). Most country, folk, and bluegrass players pick steel string instruments. The N-20’s nylon strings yield a mellower tone, and require a different technique and approach. You can’t strike the strings quite as hard, and pedal steel-like bending is largely out of the question. The other (probably more crucial) part of the equation is Willy’s influences and development as a guitar player. He grew up on the jazz-inflected sounds of western swing, and is a huge fan of Django Reinhardt.
You can really hear the Django influence in this solo — melodic single note lines, two-fingered chord voicings, tremolo picking. Good stuff.