19. Before becoming a hat aficionado, Jason used to rock a mullet.
Nowadays, it's rare to ever catch Jason not sporting one of his signature cowboy hats, but there was a time when the "Big Green Tractor" singer rocked a pret-ty impressive mullet. While the long hair might be gone, Jason's "business in the front, party in the back" motto still lives on.
Photo: © Tim Mosenfelder/Corbis