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.

In 1991, the then-58-year-old Nelson was emerging from an IRS bill and working on both his own music and a gospel album with his son, Billy Nelson. That album would be released several years later, and you can find it today. But to say it's a bittersweet release is quite an understatement. Watch the video above to fully appreciate why, and to understand how these events shaped Nelson's life today.

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 from The Boot's sister site, Taste of Country, 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, among other moments; this episode begins Season 2.

WATCH: What Happened to Blake Shelton's Brother? 

These Country Stars Know What Tragedy Feels Like