Another interpretation that just occurred to me is that the bar where the singer sings and Cowboy drinks, IS in fact the Y'all Come Back Saloon. The UNNAMED song that Cowboy requests every night eventually became the "last call" song for the bar, or the "late-night benediction" (which in this interpretation is definitely a description of the song as opposed to the name of the song). Cowboy is still broken-hearted, and to a lesser extent, so is the singer. But perhaps that pain is not stretched out over as many years or across as many states as my other interpretation.
Thoughts Posted by Trevor
Oh, one more thing that just came to me. There are some sad songs that are sung in the first person (oh boo hoo, she done ME wrong and MY heart is broken). And there are songs that are too sad to be sung in the first person, so they are sung in the third person (She done HIM wrong, and HIS heart is broken, must suck to be HIM). This song is so sad, it has to be sung in the third person ONCE REMOVED. The ORB are singing about the singer's thoughts about Cowboy's pain. You never learn what happened between Cowboy and his lost love, and that's probably for the best, because it was so horrible, you would be scarred for life if you heard it directly from him.
And all the regulars in this night club know what's going on. For most of the night, the singer is just background noise for their activities. But when Cowboy puts in his nightly request, it's time to shut up and listen. Because they are about to hear something that most living people never get to hear; the voice of an angel.
For her part, the singer is a wannabe. She'll never make it in the music business. A night-club singer is all she'll ever be. But she puts everything she has into this one song, every night. Because she doesn't want to disappoint her Cowboy. At one time, she probably hoped to win his love by knocking his favorite song out of the park. But she has long since realized it's a lost cause. But still, she loves him, and always saves her best voice for HIS song.
Cowboy clearly enjoys the singer's rendition of his favorite song, and shows his appreciation every time she sings it, by raising his glass. I suspect he even feels a connection with the singer, and part of him wants to break through his soul-crushing grief and maybe find happiness again, with her. And maybe that's why he keeps coming back, trying to find the courage to try again. But he never does. He's locked in a prison of his own making, and can never escape it. Eventually, he will drink himself to death, still broken hearted.
But the point, I think, is that, long before Cowboy started drinking himself into a stupor every night at this particular night club, he was drinking himself into a stupor every night at the YCBS in Texas. And the "Benediction" sort of became his anthem during that time. So now, he's not only pining over his lost love, he's also missing the song that became the soundtrack of his grief. So he requests that same song every night at this new bar. So it was a sort of cold comfort for him to hear the same miserable song he had grown accustomed to hearing at the YCBS.
"The Late-Night Benediction at the Y'all Come Back Saloon" (the one that the singer sings for Cowboy, not the ORB song) is a McGuffin. The idea is that there's a bar in Texas, called the Y'all Come Back Saloon, and there's a song (Late-Night Benediction) played there every night, probably at or near closing time. And it's a really sad song. That might not even be the title of the song, but a description. The song itself probably never existed; if it did, it has been overshadowed by several orders of magnitude by the ORB song of the same name.
However, "Cowboy", in turn, is still carrying a torch for a lost love, probably from many years ago. His heart is permanently broken, and he's incapable of ever loving another. So every night he drinks himself into a stupor at the same bar (probably the same table, in a dark corner) and at the end of the night, requests his favorite song, then pays his tab and stumbles back home. Meanwhile the singer desperately wishes that "Cowboy" would get over his old flame and give her a chance. But he never does. So her heart is broken too, though not nearly as badly as Cowboy's.
"She" (the night-club singer, who is, by the way, a sort of "Mary Jane" for the song's writer) is carrying a torch for one of the regular patrons of the night club where she sings (which, by the way, is NOT the Y'all Come Back Saloon, and probably is not even in Texas). She doesnt even know his name, but he wears boots and a hat so she thinks of him as "cowboy". But he's there every night.
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