I used to play in a pretty decent local country band in New Mexico back in the '90s - which is strange for a sax player, but we played some western swing, too - and we tried to keep pretty current on "top 40" country for our younger listeners - but that was the problem, they were listeners. We were a DANCE band, and whenever we'd play something new, folks would just sit and listen. Whenever that happened, our lead singer/bass player would say "key of E and follow me", and we'd launch into a 10-minute medley of Ray Price songs. Everyone in the place, ages 8 to 80, was on the floor in less than 20 seconds, guaranteed.
Classic country is still the best. How many songs from the last 10 years can you recall, and how many will people recognize 20 years from now when they hear the first few notes (with the exception of a few Alan jankson and George Strait songs)?
These days I prefer REAL Western music - it's out there but you have to look for it, try Mike Blakely - and bluegrass. And sure, I'm an old fart, but the same goes for rock, I don't follow much after Lynyrd Skynyrd and the Eagles. That's why these days I play in a jazz sax sextet and a community concert band. And singthe good old stuff at karaoke.