Bobcaygeon

On one level, this is a song about being caught in a dilemma: should you quit the bright lights for the quiet of a small town? On another level, this song may ask whether you'd like to see evil (in the form of fascism) out in the open or hidden under the surface.

In the small town, things become clear; the constellations slowly reveal themselves. In the city, on the other hand, things are not so clear. We close the blind to obscure the sky, which in any case is dull, cloudy, and "hypothetical." And in the end, he seems to favour the country, since we end up there after he thinks of quitting.

The bridge seems to refer to fascism, as "the men they couldn't hang" sing with an Aryan twang while mounted police try to restore order. The video, which casts Downie as a cop, seems to support that interpretation. On the other hand, The Men They Couldn't Hang was an 80s band which played the Horseshoe Tavern in Toronto around the same time the Hip played there, and the Aryan twang could refer to their accents (although a Celtic burr would be closer the mark).

In the end, it doesn't much matter. It's either a cop wondering whether to quit being a cop, or a singer ruminating on whether to quit being a singer.

(A side note: it's one of several Hip songs that allude or seem to allude to fascism, so it's likely that Downie considered that angle.)