These moments are sure to turn ''Devil May Cry'' into ''Devil'' Will ''Cry''. ''VideoGame/DMCDevilMayCry'' has [[TearJerker/DMCDevilMayCry its own page]].

!!''Devil May Cry 1''
* [[EtTuBrute Dante didn't take well to finding out that Trish was working for Mundus.]] Even though he saves her because ''she looks like his dead mother'', he doesn't want to see her ever again, going [[DespairEventHorizon so far]] as to put 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. 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]].]\\
'''Trish''': Dante!\\
[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 gets [[HeelRealization that]] [[MyGodWhatHaveIDone look]] on her face after that last statement.
** To think this is the scene where he's all serious instead of snarking her about it.
** 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.
** Followed by Dante mourning over Trish, leaving the Perfect Amulet and the Sword of Sparda (both mementos of his family) with her.
--->'''Dante''': (places the Amulet over Trish's heart) This was my mother' I'm giving it to you. (plants the Sparda into the floor next to Trish's body) My father's also here now. peace.
** 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... [[spoiler:his brother, Vergil...]] after he's destroyed him.
** Making things worse is Dante briefly recalling one of the few ''good'' memories he had left of [[spoiler: Vergil, before their falling out]]: the birthday in which he and [[spoiler: Vergil]] received the halves of the Perfect Amulet, a gift from their mother.
* 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]]. In the non-canon novel, Dante [[ForcedToWatch watched]] his mother be ''torn apart'' by demons right before his eyes. He's only eight-years old at the time.
** 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.
* 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 Griffon is ''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 to laugh evilly after coldly killing Griffon.

!!''Devil May Cry 2''
* Lucia in [=DMC2=] [[spoiler:trying to get Dante to kill her]].

!!''Devil May Cry 3''
* The ending. 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*
* "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...
* The final battle itself is sad. You're not fighting a gargantuan monster or an abomination out for blood. You're fighting your own brother, blood of your blood, and trying to put some sense into his head. It's not so subtle that neither of the two are too pleased with the situation, but you can feel that Dante's words are full of a "Please don't make me do this" sort of feeling.
* 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!"
* [[ 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...]]"
** Later.
--->"Good girl. Pure and Innocent... [[IronicEcho just like your mother]]."

!!''Devil May Cry 4''
* [[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.
* Nero's complete breakdown when Kyrie is kidnapped to the point he creates a crater just from punching the ground with his Devil Bringer and ends up in a huge HeroicSafeMode that Dante has to snap him out of.
* In a sort of heartwarming way, Nero asking Kyrie at the end if she would still want to be with him if he's not human. Despite all his amazing accomplishments and the lives he saved, Nero is afraid only of losing her. But she wants to be, because no one is as human as he is.
* The song "Shall Never Surrender" in general. Argh, my heart.

!!The Animated Series
* In the final episodes, Dante [[spoiler:is trapped in the Demon World, [[CrucifiedHeroShot pinned to a crucifix, unconscious and slowly bleeding out]]. Patty manages to find him and she throws her arms around him, crying and pleading for him to wake up and save the day from the demons, just as he's always done. The sheer sadness and fear of losing him as she tries to get through to him is heartbreaking.]]