What is the deal with the cowboy hats? Gary just flipped past a show called, Music with Altitude, and the person who appears to be the lead singer is wearing a large cowboy hat. My thought is the show could be called, Music with a Large Cowboy Hat. The singer could be Kenny Chesney but it's not. If it were the show would be called, Music with a Large Cowboy Hat and Singer Who Prefers the Sleeveless Look.