We talk about Willie Nelson's arrests and his bankruptcy with mischievous smiles, and we romanticize that gunfight he had with family on his property. The Red-Headed Stranger knows what real pain feels like, however. This is the story of Nelson's most tragic moment.

Season 2 of the Secret History of Country Music returns with a dive into what led up to, and what came after, Christmas 1991.

The then-58-year-old Nelson was emerging from an IRS bill and working on his own music, as well as a gospel album with son Billy Nelson. That album would be released several years later, and you can find it today. But to say it's bittersweet is quite an understatement. Watch the video above to fully appreciate why and to understand how these events shaped Nelson's life today.

Secret History of Reba McEntire's Plane Crash: 

Not long after William Hugh Nelson, Jr., died the singer offered a few tortured remarks about how he was coping. The younger Nelson's friends shared more about the problems that plagued Billy, a talented, but struggling musician living just outside of Nashville at the time of his death. It's a story without redemption or a happy ending.

The Secret History of Country Music is a weekly series that goes deeper inside the stories of country music's biggest hits, moments and figures. Season 1 explored Bobby Gentry's disappearance, the death of Blake Shelton's brother and the real reason Eric Church was blacklisted. Be sure to subscribe to Taste of Country's YouTube channel so you never miss a new episode.

WATCH: What Happened to Blake Shelton's Brother? 

These Country Stars Know What Tragedy Feels Like: