Typecasting country artists as flipping between sounding sad and nostalgic paints a limited picture that leaves out the ever-presence of humor within the genre.
Considering that the 29th of February only happens once every four years it's not too surprising that not much has happened on this date, but I did manage to find something from back in the early 50s.
Click through for the very short list for Today In Country Music History for 29 February, 2012.