Sorry folks - many of the songs mentioned I (and friends I asked last night) have never heard of. They may be big in America but not in England.
The only time I have heard Roseville Fair on a C&W night is when I have sung it - it is considered a 'folky' song over here.

If he likes 'modern' country then standards they would know would be :-
On the Other Hand - Randy Travis
Forever and Ever Amen - Randy TRavis
Diggin' up Bones - Randy Travis
The Dance - Garth Brooks
If Tomorrow Never Comes - Garth Brooks
Dont Close Your Eyes - Garth Brooks
Blue Wing - Tom Russell
Navajo Rug - Tom Russell

These along with those in my previous post would cover ANY Country night !!