5. One of his first breaks came on a reality TV show.

In 1986, Alan Jackson appeared on TNN's 'You Can Be a Star,' not as a contestant, but as a singer in the audience that got to take the show to commercial. They called him "Al" back then -- "they" being a judging panel that included his longtime producer Keith Stegall. Of course, Stegall didn't know his future was in front of him at that moment. Jackson worked in the mail room at TNN after moving to Nashville. Perhaps that's how he got the gig. It'd still be another three years after this before he released his debut single.