Sometimes I think it’s a shame when you feel like you’re winning...but your losing again.
I can’t remember the singer...it may have been Gordon Lightfoot.
Gordon Lightfoot, “Sundown”
Sometimes I think it’s a sin
When I feel like I’m winning when I’m losing again
You’re right. The song is Sundown
Yes, “Sundown” by Gordon Lightfoot.
The lady being sung about was his girlfriend who later went on to shack up with John Belushi and inject him with the final fatal dose of heroin.