For the sake of argument, I'm just going to talk about my TLV cast because holy shit, I have a lot of journals and I honestly don't spend much time wondering if Gwaine cries. Generally speaking, none of my characters are burst into tears at every available opportunity characters, and when they do get choked up or actually cry, it's a pretty rare thing, because everyone but Trip is a really emotionally weird person and even then, guys are encouraged not to cry or otherwise show weakness by our society/the society of the canon material, so it really isn't something that's going to happen often.
But they do, for the most part, all cry. :v
But they do, for the most part, all cry. :v
Dick Grayson - Dick is sort of an odd one in that he frequently goes through really rough stuff, but doesn't really sit down and cry about it, and when he's really, really upset about something is more likely to go into total shutdown versus bursting into tears. Bursting into tears is sort of saved for really truly awful things (i.e. he catastrophically loses his shit when Haly's gets burned down) and generally reserved for when he's with someone he can rely on to comfort him and won't be weird about it later, which generally means like, Alfred, Babs or Bruce, although I can see him going to Donna (or if we're using Barge history, Jim) if he needs it.
That said, I think he's one of my characters that's way more comfortable crying in front of other people? Except maybe Trip. Everyone else likes going off in private to do it, and I sort of feel like Dick either lets himself break down in front of someone he trusts or he doesn't cry. I do think he gets choked up about things (sad movies, heart warming moments, etc., the most notable I'm thinking about right now is after Mirrorverse on the Barge when Tim went home for a while he got really emotional and fighting back tears) and there are probably some very rare nights where he wakes up from certain nightmares crying, but that's way less often than it was when he was like, eight, he can generally calm down quickly and again, very rare occurrence.
The one person he will never ever cry in front of if he can help it? Tim. Dick likes presenting the image of being an indestructible older brother who will always be there if Tim needs him (and really this extends to everyone else, too, which is why he usually just represses stuff and pretends like everything is fine) and if he's crying, that kind of wrecks that image. This isn't to say it will never ever happen? But it's wayyyy less likely than Dick in a moment of utter despair crying in front of Babs.
Trip Tucker - Trip in canon I can remember crying three times: during a movie night, when he talks about losing his sister with T'Pol and when after Elizabeth dies, he tells T'Pol that Phlox found out that humans and Vulcans can have kids if they wanted to try. I think he's maybe my most emotional crier, in that when it happens, he doesn't really try to fight it and he doesn't always wait until he's alone to do it? And he's pretty legitimately weeping during the movie and despite being kind of flustered when Phlox catches him, he's not like, upset about it. So he definitely gets teared up at things and isn't afraid to get emotional with people he trusts.
This isn't to say he like, roams the halls of the ship crying at every little thing, but when he feels like utter shit or when something super heartwarming and awesome happens (like I can see him crying when like, he and T'Pol have kids when they're born and at graduations and stuff like that), it is definitely not unusual for him to cry a little bit.
Leonard McCoy - Bones crying is a pretty rare occurrence. I know that isn't really saying much because I play a posse of emotionally confused/repressive guys who all try avoiding crying if they can help it or just don't think to cry when they're upset, but Bones really doesn't cry unless shit has totally catastrophically hit the fan, and even then, I think he's a frustrated/angry crier versus being sad about something. Like, he's so angry with himself/God/the universe/whatever that after being table flippingly angry for a while and having nothing to bring himself down from it, he finally just breaks down and cries. THESE EVENTS ARE RARE and honestly I think pretty centered on like, either massively fucking up and a bunch of people died because of it, or if something horrible and life threatening has happened to Jim, because Jim is pretty much the most important person in the universe to him and losing him would be pretty soul crushing and he would 100% blame himself regardless of how it happened. This is something to be done in private and basically never in front of someone else unless he's drunk and therefore doesn't care as much, and will always, always be brushed off as not a big deal afterwards and something that should never be mentioned again.
Aside from that, I think he gets a little choked up with Joanna sometimes? In that sort of proud parent way, especially because he doesn't get to see her often and feels crummy about it. So probably when he first sees her again after being gone for a long time and then when they have to leave, there's some tearing up and super tight hugs and stuff, but he would brush off any actual signs of tears because you know. He's weird like that.
Charles Xavier - Charles I really don't think cries very often. When he's sad, he's just sad, he doesn't think to cry, and when he does cry, it isn't legitimate sobbing. In canon, he cries twice: once when he unlocks Erik's memory of his family and again after he's been shot on the beach listening to Erik say they want the same thing. Both instances were relatively unique circumstances in that I think the first had some emotional bleed through from Erik because of the telepathic connection and the second was a combination of oh my god, my best friend is turning into a monster and I really don't want him to be because I love him and was hoping he wasn't going to do this crazy shit, and also oh my god I've just been shot and it hurts really fucking badly.
So basically, I think he can get emotional and teary about really big things? Like I don't think he tears up while watching movies or anything, but for example, Ari and I are working on a thread with him and Erik where they'll eventually talk about how Charles doesn't blame him for what happened to him, and I can totally see him getting a little choked up about that, but like, it'll at most be some tearing up and a couple tears escaping, that's it. I think the only thing that could get him legitimately sobbing is like, if he saw Erik get killed or he died in his arms or something, but otherwise, he's very chill. I think he's also pretty comfortable with people crying around him? Whereas I feel like Zuko or Bones wouldn't really know what to do with them.
Honestly I think Charles in general is more comfortable observing other people's emotions and helping them deal with them than actually confronting his own and just doesn't really think to sob when he's upset. I think he grew up in a pretty emotionally distant (and if we're drawing on stuff from comics canon and I haven't really made a judgement call on this one yet, quasi abusive) household and while I don't think crying was actively discouraged necessarily? I just think Charles isn't great with being emotionally open or expressive with people in that way.
Flynn Rider - I legitimately can't see Flynn crying. At all. Like, the image of it just doesn't make sense in my brain. Even post canon with Rapunzel I can't see him crying, because if it's something really upsetting (like idk her parents passing away or something), he'd want to stay tough for her and therefore isn't going to be sitting around crying about it himself. I do think he can get sad? But crying just isn't how he expresses it or copes with it. He more like, turns to avoidance and acting like everything's alright, and otherwise he's just too confident and suave to get choked up about things. He just handles things in different ways.
Zuko - Zuko cries three times in canon that I remember? When he has a breakdown over the whole redirecting/creating lightning thing when he and Iroh are running around the Earth Kingdom, when Ozai tells him his mother might be alive and when he apologizes to Iroh for betraying him THERE MAY BE MORE, IT'S BEEN A WHILE SINCE I'VE SEEN THE WHOLE SHOW. I think he's generally a frustrated/angry crier, like when he legitimately has hit a wall and is at rock bottom (i.e. like he was in the Earth Kingdom), but it needs to be a legitimate rock bottom moment for it to happen. He's a tough kid and usually turns to getting table flippingly angry before he thinks to cry, so it's not really a common occurrence?
I think hearing Ursa was alive was more tears of relief and his crying with Iroh was thinking he'd never be forgiven and feeling like utter shit for what had happened, and worrying that Iroh would be really upset with him for what had happened. They're pretty setting specific and I can't see him breaking down all the time over every little thing, but he definitely doesn't try to hide it when he does get upset.
BONUS ROUND: Heero Yuy - Honestly? I don't think Heero knows how to cry. He knows what being sad feels like and I think there have been very few moments where he's had tears develop? But actually crying or sobbing is an emotional response I think he just doesn't understand and doesn't think to draw on when he's struggling. He's much more likely to just totally shut down and not do or think anything much for a while and eventually he'll wander out of it, and after being on the Barge, he'd accept a hug from someone, but that's it. He doesn't cry.