Alan Jackson doesn't make the rules, he just — actually, he kind of has made the rules since the early '90s. This episode of The Secret History of Country Music shows how the Country Music Hall of Famer is a bad, bad man with big, soft heart.

You may know him as the soft-spoken, mustachioed "Chattahoochee" hitmaker, but during his 30-plus year career in country music, Jackson has done things his own way. He bucked the system with two edgy songs at the height of his popularity and more or less told esteemed institutions like the CMA Awards and ACM Awards what he thought about their rules and regulations. The results were not banishment, but acclaim: More awards, even better performance slots on major awards shows and a deeper catalog of hits and satisfying love songs, done his way.

Contrast this to 2019, when artists will be (and have been) banned from awards shows for playing a little too long, or not quite long enough during industry sponsored showcases. The art of speaking up gets lost in the golden era of social media, but Jackson had it perfected. He stayed loyal to his heroes, like George Jones. Do you recall the time he pivoted mid-performance to make sure the Possum got his moment at the 1999 CMA Awards? Many years later he was there, propping up a community as he sang "He Stopped Loving Her Today" at Jones' funeral.

Watch this week's Secret History of Country Music to learn even more moments from Jackson's rebel past, including the story of how he met his would-be wife Denise. His tactics are not advisable today, but you can admit he had moxie — the moxie of a country rebel in the making, perhaps.

The Secret History of Country Music is a new weekly series hosted by Taste of Country News host Ania Hammar. We'll go deeper inside the stories of country music's biggest hits, moments and figures. Be sure to subscribe to Taste of Country's YouTube channel so you never miss a new episode.

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