Here's my take. It might be 20 years late, but still.

Well, the smart money's on Harlow* and the moon is in the street
And the shadow boys are breaking all the laws
And you're east of East Saint Louis and the wind is making speeches
And the rain sounds like a round of applause

//Harry Harlow* was an American psychologist best known for his maternal-separation, dependency needs, and social isolation experiments on rhesus monkeys, which manifested the importance of caregiving and companionship to social and cognitive development.
//This first bit is about Needing love and care. The shadow boys havn't got that care. Rain and wind are ways to paint up a gloomy mood.

And Napoleon is weeping in a carnival saloon
His invisible fiancee's in the mirror
And the band is going home, it's raining hammers, it's raining nails
And it's true there's nothing left for him down here

// I don't know the significance of the name Napoleon. It appears severeal times during Waits's career. But I read this bit to be an enhancer of the lonely man. Another lonenly man is missing his love, maybe he never had one or maybe she's been lost.
More rain. More gloom.

And it's time, time, time
And it's time, time, time
And it's time, time, time, that you love
And it's time, time, time

//It's tricky to tell if it's time that he loves, or if it's time TO love. I honestly can't tell what fit the narrative best.

And they all pretend they're orphans and their memory's like a train
You can see it getting smaller as it pulls away
And the things you can't remember tell the things you can't forget
That history puts a saint in every dream
Well, she said she'd stick around until the bandages came off
But these mama's boys just don't know when to quit
And Mathilda asks the sailors "are those dreams or are those prayers?"
So close your eyes, son, and this won't hurt a bit

//This bit is probably about drinking (because of the lack of love). They _pretending_ to be orphans are self pity in their loneliness/lack of mother figure (Read C.G. Jung for some of that deep stuff). Memories diminishing/dissapearing meaning they
drink their brains to mush. Cant remember tell the things you cant forget MIGHT be about idolizing the good parts of a previous love, and forgetting the bad stuff. Ergo History puts a saint in every dream (mind you theese dreams seem to be spirit-fueld
remembrances of lost/lack of love, right?). Also. Mathilda is Tom's name for Booze in Tom Traubert's Blues.

Well, things are pretty lousy for a calendar girl
The boys just dive right off the cars and splash into the street
And when they're on a roll she pulls a razor from her boot
And a thousand pigeons fall around her feet

// This bit is tricky. The Calendar Girl might be Mathilda, or perhaps the calendar girl is a representation of time watching from the walls, IE. The eyes on the girls on the calendars see everything the men do in their delirium. The diving of cars and
splash in to the streets might mean falling over in the rain, or plainly speaking in their misery. And when they're on a roll, when the drinking men indulge in misery, the watchfull eyes of the calendar girls get broken hearted over seeing is so that she
use the razorblade on hersel, and a thousand pidgeons fall at her feet. Pidgeons representing innocence. Something like that, or maybe not.

//Alternative idea: Maybe The calendar girl is the unrelated women on the street that the drunken men help themselves to/catcall to a degree that the calander girl find uncomfortable and she uses a razor to protect herself. The loss of innocense idea
translates.

So put a candle in the window and a kiss upon his lips
As the dish outside the window fills with rain
Just like a stranger with the weeds in your heart
And pay the fiddler off 'til I come back again

//the candle and the kiss surely is a way of caring for someone in a bad state, even though gloomy times are upon you/them (dish filling with rain puts a time dimension on the gloom which might indicate that it's a long suffering and not just a shower).
A stranger with the weeds in your heart might be that you/she/they dont recognize the passed out drunk man, but they know they love him when he's sober. Pay the fiddler of = face the concequences of the actions (the careres or the carees?)


ERGO: Men drink because they lack love. This has causes and effects upon strangers and those close to them. The drinking men need love and care so that they can stop drinking. A disease is not cured with blame.

BUT That's just my quick analysis. And what do I know, really?

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