I know of a play called "Shadowlands", it's about C.S. Lewis and his wife, Joy Gresham.  There's a scene where (SPOILER ALERT) after Joy has died, Mr. Lewis is talking to his stepson about the boy's mom, and breaks down and sobs.  In the movie, C.S. Lewis was played by Anthony Hopkins.  Fairly good scene, but I vaguely remember that there were no real tears, just acted crying.

Okay, well one I thought of (ahh I have such a bad memory for these things!) is On the Town. If I recall, there was both male and female crying in it (plus the entire theater, including all the guys, were in tears.... minus my friend and I, which was awkward)

I'm about to read a play for one of my classes, so if there's anything noteworthy I'll make a post. Unfortunately, I think I'll have to mostly record ones from shows I see from now on, because my memory honestly sucks (which means, I think, that I've never seen any truly GREAT crying scene other than in Death of a Salesman, because surely it would have stuck with me.) Question - should I bother recording small-time plays that probably won't be put on elsewhere other than in NYC because they're not well known and off-off-off Broadway?

More info than I usually like to put out there, but I attend college a couple hours away from NYC. I get depressed when there aren't enough trees around, so I usually avoid the city, but I'm in the area