"My Heroes Have Always Been Cowboys" (1980)
Shooter Jennings once lamented in song that "your heroes turn out to be assholes," but he could have easily used "cowboys" as a synonym for the coarse slur. While Nelson never overtly equates cowboys with selfish jerks in this bittersweet ballad, it's easy to read between the lines. Written by songwriter Sharon Vaughn, "My Heroes Have Always Been Cowboys" was cut by Waylon Jennings for Wanted! The Outlaws, but it was Nelson who rode it to Number One with his 1980 version recorded for the Robert Redford movie The Electric Horseman – in which Nelson made his acting debut. The lyrics romanticize "the cowboy ways," but in the end, the song is really about squandered chances and coming to terms with a life lived without responsibility. "Just take what you need from the ladies and leave them with the words of a sad country song," Nelson sings. It's more mournful admonition than boast, and by the time he see his creative prime in the rearview – the result of "picking up hookers, instead of my pen" – you can feel the regret consume him.