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Wilco – Dreamer In My Dreams Lyrics 15 years ago
Maybe I take a very negative view of Wilco songs but I read this one to be Tweedy writing about the effect that fatherhood is going to have on his lifestyle and his songwriting. Just as he's starting to get comfortable in his own skin, here comes this child which threatens to shake it all up and rearrange his life.

As a father of two, I know exactly what that felt like.

Wilco – Company In My Back Lyrics 15 years ago
NorthWriter is correct. I'm pretty sure this one is about Tweedy's struggles with migranes.

Wilco – Ashes of American Flags Lyrics 15 years ago
I think the key to this entire song lies in the line:

"This Machine Begs For Luck".

Given Wilco's previous involvement with Woody Guthrie, it appears that this line is a takeoff on the famous Guthrie slogan that was spelled out on his guitar:

"This Machine Kills Facists".

The lines that bookend the song are classic Guthrie -- Finding the beauty and emotion in everyday items of Americana.

The interesting part of the song is in the middle. In stark contrast to Guthrie's pointed political statement, Tweedy is telling us that he wishes that his music and lyrics were up to the standards of his poetic heroes like Guthrie. The whole song reads to me like an artist who isn't entirely comfortable with the validity of his work.

"All my lies are always wishes", "I shake like a toothache when I hear myself sing", "A hole without a key if I break my tongue". It's about self-doubt as a creative person, in my opinion.

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