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Townes Van Zandt – To Live Is to Fly Lyrics 16 years ago
I agree that the song is about learning from the past. I also think it's about not holding on to the best parts of your past.

Goodbye to all my friends
Its time to go again
Think of all the poetry
And the pickin down the line
Ill miss the system here
The bottoms low
And the trebles clear
But it dont pay to think to much
On things you leave behind.
I will be gone
But it wont be long
I will be abringin back the melodies
And rhythm that I find.

In this paragraph he is saying that he found a place where he was welcome and the sound system was great and he'd love to stay, but there is more to be found in the future than in the past.

Townes is great because he forces you to think about what you're hearing.
Rain, up and down it comes, like rain on a conga drum" How can rain go up and down? Doesn't it only come down? Unless, it hits a conga drum and ricochets upward. He's brilliant.
Also, mentioning Jimmy Buffet in the same breath as Townes is shameful to me. Buffet pales in comparison to Townes in every literary sense.

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Wilco – The Late Greats Lyrics 16 years ago
Music is susceptible to interpretations and this song is indirect. With those two elements combined you have a song that breaks the boundaries of meaning. If you hate corporate records you'll see this as a slight against "Pro-Tools" and the Pro- Tools that run the industry. If you hate snobby Indie Rockers then you'll see it as a slight against them. The meaning lies in the agenda of the listener.
From what I gathered, Tweedy is not a Dylan type lyricist. Unlike Dylan, he isn't trying to loose you in the words, he wants you along for the ride. So, his lyrics are predominately transparent. The deduction of my constant pontificating is, that Tweedy was saying that there are some great bands that will never be signed. He isn't trying to make a blanket statement about the record industry. He's saying there are some bands that will be great and never signed (The late Captain Nowhere for example).
Best of all this is another timeless, catchy song, by a band that seems to be good for at least three of these a record. I think this song was added on the end of the album as a release from the depression and somber melodies of the rest of the album.

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