Ichi the Killer. Granted you could see it coming but still.
The man crying was the one in black, Ichi. What the scene doesn't show was Kakihara shooting him in the leg. The entire movie builds up Ichi, showing all of these fantastic acts of hyper-violence he's been perpetrating. Kakihara is the opposite (the masochist to the sadist that is Ichi) Anyway, he shoots Ichi in the leg which reduces Ichi to a bloody heap, crying. Kakihara punctures his ear drums with his needles, fantasizes about the fight that should have been and, hurls himself off of the building. Meanwhile a child beats the hell out of Ichi (Ichi having killed the kid's dad earlier in the movie)
Overall, I really liked Ichi the Killer but the ending was a let-down. Also, for clarity, When I say, 'you could see it coming' I forgot to mention that Ichi always cries during his massacres. A mysterious contractor gives Ichi instructions and money, claiming the people Ichi is about to kill were the kids who bullied Ichi as a child.