Whether hes the lead
https://www.youtube.com/watch?v=kIdbsL7Oxb0
Or he surprisingly shows up in someone elses song.
https://www.youtube.com/watch?v=JgZ1zfwma80
https://www.youtube.com/watch?v=evtmVZFeooA
Is it because he is a little unpolished so he sounds like your grandad?
Of course if you dont like Willie then this thread doesn’t apply.
Willie has no anxiety in his voice at all. His voice speaks of calmness, control and acceptance no matter the subject matter.
Don’t discount the sound of “Trigger” (his 50-ish nylon-string Martin) following his singing.
His voice is mellifluous.
^ A 10-cent word, however, totally correct.
He doesn’t employ that nasal twang thang the other country singers (ab)use.
He means what he sings.
Agreed. He sings plainly about human themes that are familiar to all of us. He doesn’t use the fake kuntree-fried affectations or posturing other CW singers do. Plus he smokes weed and has girly ponytails.
What’s not to like?
kayaker, I may have used “10-cent word” incorrectly and apologize profusely. 
Willie is believable. Like Johnny Cash, he sounds like he really means what he is singing.
Plain and plaintive is a wonderful combination. He needs no flourishes to get to his point in whatever song he is singing.
I’m not a huge fan but like the man and his music enough to comment. To me his voice sounds approachable, safe.
This thread speaks to me, but like the OP, I don’t have an answer. I listen to Willie’s Roadhouse on Sirius/XM quite often, and whenever a song he’s singing on comes on, it’s like I can breathe deeper and I’m more relaxed. His voice shouldn’t be such a beautiful thing, but somehow it is.
ETA: His voice is sorta like a steel guitar: Sounds good in the background, sounds good up front, it cries, it comforts, it has a natural twang.
I’d probably call “mellifluous” a 25-cent word, a multisyllabic word that is perhaps pretentious. I thought a 10-cent word was the pretty much the same thing, is there some other meaning to it?
I was thinking along the same lines.
Willie Nelson sounds like he should be narrating a Rankin/Bass Christmas Special.
I actually looked up the definition of the word prior to using it! 
OK, here goes:
My 10th grade English teacher was the nicest man you’ll ever meet (doubly so as a teacher). His constructive criticism was more “I want your story to be even better” than “you fucked up again.” In a short-short story of mine, he circled “inexorably” and wrote “a 10-cent word” in the margin and since then it’s meant, to me, a word that classes up the joint, and I’m sure that’s how he meant it. When I tagged kayaker’s post (mellifluous) as such, it occurred to me that maybe the usage was incorrect–indeed, it seems to imply pretentiousness. I would never insult kayaker, who’s not only a decent gent but a Pennsylvanian. Hence my apology.
As for TriPolar, due to inflation, a 10-cent word in 1975 has got to be a 25-cent word today, so I will adjust my usage accordingly; thanks.
Sorry for the hijack.
PS Mr. Meyer, if you are out there, you have left your mark. Kudos!
Thread winner.
That’s a lot of it- Willie’s voice is unique. He doesn’t sound like anyone else, especially mainstream country, and as a result, he sounds very genuine.
I think also his songs always seems to have a bit of wistfulness or melancholy to them, which tends to make them a bit softer and more approachable.
If they would digitally take out Burl Ives and insert Willie narrating and singing, I’d watch that show again; why, it would save Christmas!
I’ve always thought he sounds like his sinuses are so utterly empty and resonant, compared to the way most of our voices sound.