Oops, still a few thoughts bubbling up...about the albums and what they reveal about Lindsey.
I don't feel like any one of his albums doesn't represent him in a very tangible way. In fact, I think Law & Order, Go Insane, and Out of the Cradle all communicate a similar sort of almost socio-political view that says a lot about Lindsey the person, even though each album is dressed up quite differently from its predecessor.
Take Law & Order's songs collectively and see how many of them touch upon the idea of personal integrity - committment to family, friends, values, trying to do the right thing. The title is all about that. The covers he selected for that album are all about that. "Mary Lee Jones" is about a woman who has lost that because she's lost herself. "Johnny Stew", an incredibly funny/goofy song, is, at its heart, about the cruelty of a world that has left a man of integrity, John Stewart, out in the cold. Given this context, I think "I'll Tell You Now" is also indirectly about Lindsey's own feelings about wondering how to fit in a world that doesn't much reflect what he thinks is important.
Look at the songs from Go Insane. In microcosm, they're about a painfully failed relationship. In a broader sense, they're also about valuing committment, responsibility to self and others & love, and trying to deal with the feelings of the loss of control when those things don't last - when those core values and desires don't seem to be able to find a foothold in the crazy world. None of these are preachy songs in any respect, but they're very internal conflicts about the successes and failures he seems to see in himself in pursuing these values. Even for all the sexual innuendo in a song like "Loving Cup", it is still a song about wanting committment reciprocated in the same strong way that he feels it.
Out of the Cradle does this too. So many of the songs seem to touch upon the idea of rediscoverying himself, his values, after a period of having felt like he lost touch with them. I'd say this one is more sober than Law & Order, certainly, but not nessecarily more "serious" - as I think Law & Order was just as serious about its underlying values too. Again, Cradle seems to touch upon the pressures of life that intrude upon what he wishes it could be, and he ruminates on the successes and failures against the measuring stick of committment, family, friends, values, responsibility.
I think a similar type of theme can also be seen underlying many of his Mac songs. That's how I see them anyway.
