The song "A Hard Lesson To Learn" by Shooter Jennings explores themes of love, loss, and the consequences of one's actions. The lyrics reference various country music legends like Jimmy Rogers, Hank Williams, and George Jones, who have influenced Shooter Jennings. The song begins with the narrator reminiscing about listening to Jimmy Rogers on his father's old record player. He reflects on the idea that when you have love, all you have is love to lose. This sets the tone for the rest of the song, as the narrator grapples with the ups and downs of relationships. The lyrics mention Hank Williams and his affinity for drinking, hinting at the narrator's own struggles with alcohol. He describes himself as a whiskey drinking, low sinking, love 'em, and leave 'em kind of person. He acknowledges that if something is worth keeping, he often ends up losing it due to his reckless behavior. The narrator also makes references to George Jones, who faced personal and professional challenges. He compares himself to a lost highway, where the devil collects the tolls, implying that he is trapped in a destructive pattern. Throughout the song, the narrator recognizes that he is constantly learning from the lessons of these country music legends. However, he also acknowledges that he keeps making the same mistakes, falling into the same old patterns of love, loss, and heartache. The "same old bottle" and "same old blues" represent his struggles with addiction and the cyclical nature of his relationships. Overall, "A Hard Lesson To Learn" is a contemplative and introspective song that delves into the complexities of love and self-destructive behavior. The lyrics suggest that the narrator is aware of the consequences of his actions but finds it difficult to break free from the patterns he has become accustomed to.