"Two Old Sidewinders" by Waylon Jennings is a country song that tells the story of two individuals who are experienced in life's ups and downs. The lyrics depict a couple of adventurers, perhaps cowboys or outlaws, who have faced many challenges together and have come out stronger. The song starts with the narrator mentioning loading horses and packing the rig for a journey. They decide to leave everything behind, saying goodbye and walking out the door. This could symbolize leaving behind a troubled past or a difficult situation. They acknowledge that a single drink or a single kiss can often lead to trouble, as they have already experienced this before. This suggests that they have learned from their past mistakes and try to avoid the same pitfalls. The lyrics continue to describe a journey to Houston, where they only manage to get two hours of sleep in order to make it or break it. This could represent the difficult choices they have made in pursuit of their dreams or ambitions. The mention of "eight seconds of glory" refers to rodeo events where cowboys try to stay on a bucking horse or bull for the full eight seconds. This could symbolize the fleeting moments of success and fame they have experienced over the years. Despite their hardships, they continue to rely on five-year-old whiskey to wash down the dust, implying that they find solace or escape in this habit. They believe that despite their circumstances, they can overcome any challenge, as they are seasoned climbers. This reinforces the idea that they are resilient and experienced individuals who can handle anything that comes their way. In their search for companionship, they look for women who they can be honest with but can also deceive if needed. They desire someone who is impressed by their outlaw reputation, even though their once-prized possessions have lost their value over time. The mention of being "damned near broke" suggests that they have experienced financial struggles, but they continue to spend money on whiskey. They ponder if offering a bottle of wine to others would have the same effect. The reference to the two individuals near the jukebox implies their interest in finding new companionship. Overall, "Two Old Sidewinders" tells the story of two veterans of life who have faced adversity but continue to navigate their way through challenges. They have learned from their pasts, remain resilient, and seek new opportunities while still enjoying the simple pleasures of life.
