Waylon Jennings' song "A Long Time Ago" talks about his life as a cowboy singer and the struggles he faced with women, fame, and the music industry. The lyrics suggest that Waylon doesn't fit the conventional image of a cowboy singer, but he has made choices and taken risks that have shaped his life and career. He acknowledges that his actions may have been questionable at times, but he believes that people can never truly understand his experiences just by reading about them in books. The line "How it was a long time ago" indicates that his past is unique and cannot be fully comprehended or judged by others. Waylon also reflects on his relationships with women, admitting that they have caused him trouble ever since he realized they weren't the same as men. Despite this, he has been married multiple times but proclaims that no woman could confine him and his adventurous spirit. The line "I was born with a fire down below" suggests his strong passion and desire for freedom. The song also touches upon Waylon's journey in the music industry. He mentions the struggles faced by him and his friend, Willie Nelson, who have been bought and sold by the industry. They have been labeled as outlaws, referring to the outlaw country movement they were a part of. Though they faced opposition and attempts to run them off, they never gave up and continued to pursue their music careers. Waylon concludes the song by urging the listener not to ask about the hardships he endured or the choices he made. He emphasizes that these experiences have shaped him, but the listener will never fully understand the depth of his story. Ultimately, Waylon affirms that he has overcome these challenges and has chosen to stop running a long time ago, settling into his own unique path in life.