9. He first wore a cowboy hat to cover a scar.

While we now know what Alan Jackson looks like without a hat, the singer didn't originally abide by Nashville hat rules. In 1992, he told People that he first starting to wear a cowboy hat so no one saw a scar he got as a kid growing up in Newnan, Ga. As for his long hair? He explains: "Traveling around, I never had time to get a haircut, and everybody said, 'You know, we kind of like it long.'"