Tear Jerker / In Bruges

• Pretty much all of the movie that isn't comedy qualifies for this. It doesn't help that Ray is suicidal and Ken has to kill him.
  • The scene in the park, where Ray finally breaks down about killing a little boy and cries into Ken's chest.
  • "I went to the park so she wouldn't have to clean it up."
• Ken's actions for the second half of the movie. Not only does he essentially give the finger to his boss whom he owes greatly, but he spares Ray to the point of taking two bullets and dying for him. All of which has "On Raglan Road" playing over it.
  • Even worse in that as Ken is bleeding out from two bullet-wounds, he throws first coins, then himself from the top of the tower so he can warn Ray in time to defend himself - and the coins were thrown to alert the pedestrians below that something odd was happening.
    • It gets even worse. Just before Ken dies, he only has enough time to tell Ray that Harry's looking for him and that Ray is to take his gun to defend himself. A gun which is now broken thanks to Ken landing on it when he fell. And Ray ends up getting shot by Harry anyway. Ken essentially died (in a horrific manner) for nothing.
• The flashback when we finally see what went wrong during Ray's hit. Everything's carrying on with the same Black Comedy as the rest of the movie, then just before the priest dies, he whispers "the little boy". Cue a shot of a boy who looks about six or seven with a bullet hole in his forehead holding the most innocently childish list of things to confess to the priest and Ray completely freaking out. It's one of the very few moments in the first half of the film played absolutely seriously.
• Only in the deleted scenes, but a few scenes show that Harry was sexually assaulted as a child in Bruges by his father or someone he trusted. These short flashbacks are juxtaposed with him travelling to the places from his childhood when he returns to Bruges to kill Ray. This also ties in to the reason that Harry wants Ray dead after his mistake(and Ken even says in the film proper that Harry has a sort of mania about protecting children. It gives a deeper motivation to Harry's enmity.
• Most of Ken and Harry's scenes carry a sense of sadness; not only do they act like old friends despite Harry arriving to kill Ken, the two are visibly reluctant when they struggle with one another, with Harry even apologizing to Ken when he shoots him fatally.
  • They even manage this when they're not in the same room; when they have their phone conversation, it starts off hilariously as Ken tries to fake the fact that Ray is already at the pub... and then Harry starts referring to Ray in the past tense. You can see Ken's world start to shatter at that point.
• Harry killing himself after he mistakenly thought he killed a child (it was actually Jimmy). Foul-mouthed and violent as he might be, the fact that he earlier said he would do this in the right circumstances and then follows through on his word, with a devastated expression as he says "Oh...I see..." Roger Ebert said it best: "[this event] shows that even professional murderers have their feelings." The fact that Ray (the man Harry just shot multiple times for doing the same thing) is urging him not to do it makes it worse.
• In an odd sort of way, Jimmy's death. He doesn't even really know Ray that well, only became sort-of friends with him a few days earlier and has acted like a bit of a jerk for much of the time, but he sees Ray clearly in trouble and goes to try and help...and gets his head exploded by a bullet for his efforts. Ouch...
  • Even worse is that a mortally wounded Ray crawls to his corpse afterward.
  • Also despite Jimmy's earlier unpleasant outbursts, he seems genuinely apologetic when he sees Ray for the last time. After his initial anger he seems ashamed of his behaviour. He even parts on a happy and reconciliatory note, inviting Ray to the film shoot. It makes his death feel a lot more unfair than if we'd not seen him since the party.
• Chloe seeing Ray getting loaded in the ambulance.
• The final monologue is quite possibly the most emotional moment in the entire film. Ray's epiphany about the nature of Hell, guilt, redemption and judgement is capped off with the repeated line "I really, really hoped I wouldn't die." Even with the comedic mentions of Bruges, it's hard to get through it with dry eyes.