3. Cyclops - X-Men 1, 2 & 3
Wolverine is awesome. Annoyingly awesome, even more so because in the franchise, everyone else seems to be lackluster (again, no disrespect to McKellan and Stewart), and the top dog for wimps is Cyclops. A natural-born leader...who never leads. One of the greatest powers of destruction, that he almost never uses. And the (almost) quintessential crybaby. Before anyone was thinking about how emotional a scene might be, Marsden's character was there to remind us that while it's ok for men to cry, one might be overdoing it a little bit. All in all, it's a sad day when such an iconic character dies in the first five minutes of film, and everyone is happy about it. Hopefully younger Cyclops is willing to do more than sit in the corner and have a good sob. Speaking of sobbing...
2. Spider-Man - Spider-Man 3
I honestly couldn't tell who cried more during this film. Was it Tobey Maguire, or the fans that just couldn't believe our neighborhood wall-crawler had sunk so low? And sink he did. The go-to film for what not to do with superheroes, Peter Parker's descent into "villainy" was more showing how much the brainiac did not understand what jockdom really was. Given a suit with amazing powers, that can simulate any manifestation of your arrogance, and what do you think the best thing to do is? Walk down the street in jazz style, with more product in your hair than a production of Grease? As much as one scene was despicable, it did not define the entirety of this character's descent. One of the most unforgivable parts of Spider-Man in the movie was the fact that he did almost nothing to resolve his conflicts. He was completely willing to kill someone under the black suit, but once it was gone, it was like Spider-Man was neutered. No fighting, no real quips, just more begging for the pain to stop and wait for Deus Ex Machina. I hated that it only took five years for a reboot, but it only came too soon.