I have a good friend that is in the Canadian Music business.A couple of years ago he mentioend that "Sundown" was Bruce Cockburn's nickname and it is written about an affair he had with Lightfoot's wife. Most of us from Richmond Hill (us lucky ones escaped) have heard that Brian Good was the actual dude sneakin' around Lightfoot's back stairs. largely thanks to Lightfoot and his music industry connections. This is definitely about a woman he cares for and worries about her fidelity. He feels like he's winning but he's losing again because he can't stay away from her, even though he should. If you don't get that, you haven't f--ked the right girl.Gordon Lightfoot could write a tale, and most were true! Anyone who's seen Gordo in concert knows that he wrote the song at a time in his life when his wife was divorcing him.I still feel like a naughty little girl when I hear it... To me this song represents my time in the navy going over seas(asian countries) and meeting women at "buy me drinky" bars.because I was sneeking around behind a very strict family to even be kissing a boy... Where we would fall in love with the women and then have to leave.
I think we can say for sure there is reference to infidelity in a relationship as well as to alcohol.
He feels like he's winning because she is there with him and he feels good, but his is really losing because her love is fleeting. I haven't figured out the "sundown" reference in my mind, but I'm in love with the lyric "Sometimes I think it's a shame when I get feeling better when I'm feeling no pain" It's kinda sad and deep The room where you do that you don't confess... He is in a relationship with another women, but his ex is a great lay.
While alcohol is the most probable meaning, it can also apply to depression, which often accompanies alcoholism."Sometimes I think it's a sin when, I feel like I'm winnin' when I'm losin' again" I think means that he knows the woman he is with is not good for him and cheating on him but he feels comfort being with her anyway.
This song always sounded like a song about rape to me.
"I can see her lyin back in a satin dress/in a room where you do what you don't confess" plus the part about you'd better "take care" if creeping down a back stair.