Never. I'm controlled with my drinking due to the death of a good friend when we were almost teenagers by a DUI.
But I have heard many men cry while drunk now that I think of it. Hmm...
All the time in my past when I use to drink while listening to depressing music because i was depressed... not so much now that is a very long time ago in my past. I use to drink every night and listen to depressing music to further my own self destructive behavior. I barely drink now and when i do its not because im upset.
As I recall it was fun for various reasons but I wouldnt find it so anymore.
I don't cry a lot ever, but I don't think I've cried once while drinking. If I'm to the point where I've given myself permission to drink, I'm past the point of caring enough to cry.