These moments are sure to turn ''Devil May Cry'' into ''Devil'' Will ''Cry''.
* DMC 1 has Dante [[EtTuBrute didn't take well to finding out that Trish was working for Mundus]]. Even if he saves her because ''she looks like his dead mother'', he doesn't want to see her ever again, going [[DespairEventHorizon so far]] [[MoralEventHorizon as to cross the line]] by [[ShootTheDog putting her at gunpoint]], shouting that even if she looks like his mother, Trish is just a soulless demon, then drops his gun, and walks away in anger and sadness. [[NiceJobFixingItVillain Way to go, Trish]]. You made everyone cry because of that.
-->'''Trish''': "Uh... Dante! Dante, [[EvilCannotComprehendGood why did you save my life?]]"
-->[There is a pause and Dante looks away.]
-->'''Dante''': "Because you look like my mother... Now [[GetOut get out of my sight]]! The next time we meet it wonít be like this."
-->[He starts to walk off again and [[PleaseDontLeaveMe Trish moves to stop him leaving her behind]].]
-->[Dante spins around brandishing one of his handguns, held pointing at Trish.]
-->'''Dante''': [[RejectedApology "Donít come any closer you Devil!]] [[TheReasonYouSuckSpeech You may look like my mother but you're nowhere close to her. You have no soul! You have the face but you'll never have her fire!"]]
-->[He drops his handgun and walks away]
** Trish even makes [[HeelRealization that]] [[MyGodWhatHaveIDone look]] in the face after the last statement.
** To think this is the scene where he's all serious instead of snarking her about it.
** Before that, there is a revelation of Nelo Angelo: [[spoiler:It's Vergil!]]
** And then she takes an attack from Mundus that was aimed at Dante, and apparently dies because of it. His tears after the first two battles with Mundus can make anyone weep.
** How about when Trish tries to apologize to Dante for selling him out to Mundus, she has TearsOfRemorse?
* Dante realizing who Nelo Angelo ''really'' was... after he's destroyed him.
* Lucia in [=DMC2=] [[spoiler:trying to get Dante to kill her]].
* From the bits of Dante's backstory we see, he was a happy and carefree child. Then he loses his family during a demon attack [[FromBadToWorse and the rest of his life became a lot worse]].
** It seems to be the same for [[spoiler:Vergil]], which makes it even ''worse''. Depending on whether you consider the manga canon, it gets very, ''very'' worse... and never really gets better.
* The ending of Devil May Cry 3. First there's the part where [[spoiler:Vergil tells Dante to return to the human world and takes a very deliberate, implicitly suicidal fall off the edge of the cliffs where they fought.]] Knowing his REAL fate actually makes it worse in a way. But the icing is when [[spoiler:Dante cries for his brother -- and, being Dante, says that it's "[[SandInMyEyes only the rain]]."]] *sniffle*
* [[spoiler:[[RedemptionEqualsDeath Credo's]] death]] in [=DMC4=]. Him begging Dante to [[spoiler:save his sister and Nero as he bleeds to death after being stabbed by Sanctus]] is the icing on that particular cupcake.
* "Might controls everything. Without strength, you can't protect anything." This line just oozes past guilt from Vergil about not being able to protect someone he loved. The person in question is likely either his and Dante's mother or, if you buy into the semi-confirmation that Nero is his son, his lover/Nero's mother.
** Given the way he crushes Dante's half of their mother's amulet against his forehead, and the brief but absolutely stricken look on his face...
* Dante's final words in [=DMC3=] also count as this. After a really long, downright ''horrible'' day where his home has been destroyed, he's been battered around, and just had to watch his brother choose suicide over being redeemed, he doesn't even get a break, being attacked as soon as he's out of the tower. His BadassBoast sounds more like he's trying to convince ''himself'' that he's okay and ready to take on the world.
--> Dante: "Well, bring it on! I love this! This is what I live for! I'm absolutely crazy about it!"
* [[VideoGame/DmCDevilMayCry DmC: Devil May Cry]] has [[TearJerker/DmCDevilMayCry its own page]].
* While the Griffon boss in the first game was a pain in the ass and a demon, there is just something tragic about his death. [[spoiler:After being gravely wounded by Dante, he begs Mundus to help him, to give him just one last chance to prove his worth and destroy Dante. Mundus cruelly denies him this, shortly before [[YouHaveFailedMe zapping him to cinders]] while ''begging'' Mundus not to.]] If you did not think Mundus was an utter bastard before, [[MoralEventHorizon you will now]]. Dante certainly did. Mundus also had the audacity the laugh evilly after coldly killing Griffon.
* [[https://www.youtube.com/watch?v=UseDERBcNY4 Arkham's "redemption"]] [[DeathEqualsRedemption upon his death]]. For a few seconds, Lady got to believe he wasn't the ManipulativeBastard she thought he was, to then watch him fade (thinking he was just another victim). Words can only faintly describe what she must have been feeling [[YankTheDogsChain when it turned out he was still manipulating her even then]].
-->"You're such a sweet child... [[SoProudOfYou just like your mother...]]"
-->"Good girl. Pure and Innocent... [[IronicEcho just like your mother]]."