songs that he and his friends could sing along to
There are so many periods within C&W, with so many differences, that coming up with what will please him is difficult without knowing what he's into. The good news though is that you can easily find chords for most of the older, well-known ones at Cowpie. Can a secret agent plumb his record collection to see what he has that looks well-worn?

If it's contemporary country he likes, CMT-TV has songs you can hear (as videos) right online.

~Susan