Lyric discussion by LonelyHikr 

251 takes on the meaning of this song, guess I'll add another... My favorite songs are the ones that embed layers of meaning. Many of the meanings discussed previously make sense and I imagine many of the ideas were in Mercer's mind at the time of writing. But let's take this to a different level and look for another way to roast this chestnut:

James chose an alternate path, alternate life for himself. He chose this course during those formative years when most of us fall in love, settle into a nuclear family, and settle into the 9 to 5 with two weeks vacation. Some would say aging but not living.

James regrets that the love of his life rejected him. Maybe if he'd kept his mouth shut... Although, maybe if she had accepted him, he would have married and settled into the 9 to 5 working stiff lifestyle to support a family. Would that really have been better?

The life he has chosen has been difficult. It would have been easier to live a life of quiet introspection if he came from a rich family or inherited a prosperous business. But maybe the reward is the vision you gain through the struggle; the perspective on life that few people understand, as most don't take the time to experience it for themselves.

But James has, and when he looks out into his lemming town he is both sickened by everyone he sees, and a little jealous.

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