Is there a rule of thumb about how many times a man can cry in a movie?  
The screenplay I'm working on has some very emotional scenes, but I'm holding back because I don't won't my guy to come off as a punk.  

Now, I understand if a group of men sitting around talking about past relationships, and they get emotional and tear up like water falls... yeah, I would see that as punkish.

But a powerful love story which takes this man on an emotional roller-coaster ride.  Can he have at least two crying scenes, and maybe "a single tear rolls down his cheek" scene, and still be looked at as a manly man... or is one the limit?

I think a bunch of men talking about past relations and, suddenly, start crying would be very comical.

Your character probably wouldn't come off as a punk but, rather, a wuss.


Phil

The only time i've ever been moved by a man crying in a film, was by Sylvester Stallone.  He, for some reason, can pull it off and never lose his edge.

No need to overthink.  Men get choked up all the time.  Just use common sense.  

But JMHO... What's important isn't that the character cries, it's that the audience cries.

Ghostie  

Once and he has to lose something deeply meaningful. After that it's time to change or make changes, ala Sly Stallone. Anything more is wallowing, unless that is your character.

You just gotta do it right, man. In Blue Valentine, Ryan Gosling sobs like a baby and it just flat out works. For Ewan McGregor to cry in Moulin Rouge... not so much. The dude's a solid actor but that was just embarrassing. And it was at the most "serious" moment in the film too.

I think if it all leads up to it and fits the scene then it should be fine. A great example is when Matt Damon cries in Good Will Hunting, one of the best breakdown scenes I have seen.

Quoted from nawazm11 I think if it all leads up to it and fits the scene then it should be fine. A great example is when Matt Damon cries in Good Will Hunting, one of the best breakdown scenes I have seen.

I also agree, if it fits the scene.  I guess after it's all said and done, and if my character seems a little too sensitive... I might have to tone him down.

The rule is once. Not a tear more.