After a little time spent thinking about it, it's not too surprising that heroes can often sympathize with certain villains. When you have heroes like the All-Loving Hero around, they're always looking to redeem and relate to anyone, and heroes that have a Dark and Troubled Past can surely understand how sometimes those experiences can put someone down a path to villainy.
What's more surprising is when villains, morally grey characters, or an ordinary Innocent Bystander who are not famous or admired look at the hero, and say "Man, it sucks to be him." Sometimes these people see how Being Good Sucks and No Good Deed Goes Unpunished, and it causes them to feel genuine sympathy and pity for what the hero goes through in being heroic. For the first two, it tends to serve as a Pet the Dog moment.
This can easily serve as a lead in to a villain making a Not So Different speech, seeing the hero as a Worthy Opponent, offering to rule together, or, more darkly, trying to Break Them by Talking, etc.
Compare It Sucks to Be the Chosen One and Antagonist in Mourning. When the villain sees the hero going through so much shit and cannot understand how they can still be heroic after that, it's often because Evil Cannot Comprehend Good. Compare and contrast Baddie Flattery. Sympathy for the Devil is the inverse, when the heroes are sympathizing with the villain. See also Hurting Hero, which is often what leads to this.
- A surprising number of villains feel bad for all the crap the Straw Hats go through in One Piece. It usually helps show the Morality Kitchen Sink going on all over the place. Most notably, Franky, leader of a vicious bounty hunter gang, breaks into tears when he hears how Usopp left the Straw Hats to keep the Going Merry. Keep in mind, he had savagely beaten up Usopp about a dozen chapters ago, and was now holding him prisoner. This eventually leads up to his HeelFace Turn.
- In Naruto, toward the end of Hinata's fight against Neji, Neji's teacher, Might Guy appears slightly sad when noting that Hinata is no longer able to fight against Neji and gives Neji a What the Hell, Hero? when he tries to kill her. Fridge Brilliance kicks in when you remember that he's also Lee's teacher, and he strongly identifies with those who are trying to take down a more talented opponent through hard work and determination.
- Saki Achiga-hen, Toki has a moment like this with Kuro, who is beginning to despair when facing the champion, Teru, and is not able to fight back effectively. Toki notes that Kuro, by attracting all the dora tiles, is hindering Teru's ability to make progressively larger hands, and is quite pleased with Kuro when she finally discards a dora tile, enabling her to win off Teru.
- In Dragon Ball Z, in spite of being enslaved by Babidi's magic, Yamu was genuinely repulsed by his partner Spopovich's Cold-Blooded Torture of Videl and even urged him to stop.
- In Attack on Titan, Reiner Braun, despite what he says to his relatives, apologises directly for being responsible for what's happened to Eren Yeager and his friends and family. In the same scene, Eren shows some of the opposite of this trope, along with admitting that they're Not So Different. He still transforms into a Titan and kills Willy Tybur and a number of innocent bystanders, however.
Black Tarantula: I applaud your dedication, Spider-Man, as well as your sense of honor. Considering the current bounty on your head, only a man of exceptional virtue would risk himself to save the heir of an enemy!(Short pause as he really hits Spidey hard.)Black Tarantula: ...which makes my own task all the more difficult. (hits him again). While the local authorities may mistake you for a criminal, those who lurk in the shadows see your true heroism! (Stops fighting, as Spidey clearly can no longer fight back.) Ironic, isn't it? Your enemies know you better than your allies. note
- In one story Spidey confronted by the Argentinian crimelord (and very powerful superhuman), the Black Tarantula, who seeks to kill the hero in order to seal a bargain with another crimelord. Black Tarantula proceeds to curb-stomp Spidey, wondering aloud why he refuses to quit when everyone is after his head. Then he finds out that the reason is, he's looking for the kidnapped Normie Osborn:
- In another story, Hammerhead hires the Hobgoblin to assassinate Joe Robertson; the villain has Joe cornered, and gives him a chance to beg, saying "I always love hearing a good grovel." Joe refuses, having learned a thing or two about pride in the previous story. The Hobgoblin grins a little and says, "I respect that, Robertson." (Palms a grenade.) "Not that it's gonna save you. I just respect it." note
- During the Kindly Ones volume of The Sandman, Lucifer notes that while he once swore to destroy Dream (over a fairly trivial matter) he now feels almost sorry for him when he sees the mess that Dream has gotten into.
- In Captain Atom: Armageddon, Cap gets a lot of this, especially from Mr. Majestic and the Authority, who both recognize that Cap is a good man and a hero, and that it's not his fault that he's going to blow up and destroy the universe. They do their best to help him, and Angie Spica, the Engineer, a member of the Authority, even gets romantically involved with him. That doesn't stop her, and the rest of the Authority, from trying to kill him, in the mistaken belief that that will stop him from destroying the universe.
- In Knightfall, Bane engineers a massive prison break at Arkham Asylum just when Batman is already sick and rough around the edges, knowing Batman's own worst instincts will compel him to bring them all in personally. Watching him afar, he concludes that if he didn't want Batman's blood so badly, he'd pity him.
- There's a scene in The Prophecy where Satan briefly commiserates and shows sympathy to Detective Daggett (a cop who years earlier lost his faith just before he was set to become a Catholic priest) about how hard it is to believe and keep faith.
- Villain Protagonist Yuri Orlov shows a grudging respect and admiration for Hero Antagonist Agent Valentine several times in Lord of War. Specifically, Yuri goes out of his way to point out Valentine's honesty and integrity, and Yuri seems to be showing some sympathy when Valentine is about to be betrayed by the system he has risked his life defending.
- In the 2003 film version of Peter Pan, Hook uses a Breaking Lecture on Peter to take away Pan's flight and distract him. Throughout it Hook talks about how Wendy will grow up, and move on, leaving Peter to die alone, forgotten, and unloved. At the end he suddenly looks tremendously sad and adds "Just like me".
- Spider-Man Trilogy:
- After Spider-Man saves the train from falling off the tracks in Spider-Man 2, he's exhausted and almost falls off the train. The people in the train pull him back in and lay him on the floor. Peter's lost his mask in the fight, so everyone in the train can see how young he is. One man notes with sympathy, "He's... just a kid. No older than my son." One young bystander gives Peter back his mask, and they promise to keep his secret. Then when Doctor Octopus returns, they all vow to protect him. Unfortunately, Doc Ock doesn't have a problem with that.
- The first movie also has Innocent Bystanders coming to Spidey's aid when he chooses to save both MJ and the children, enabling him to succeed and disproving, at least for the moment, the Green Goblin's claim that eventually the people will come to hate him.
- The Joker often tries to relate to Batman throughout the course of The Dark Knight, especially in expressing how they're both freaks on the margin of society. At the very end he even grudgingly praises the fact that Batman is incorruptible, and cannot be made to break his moral laws. Unfortunately he had a backup plan, and succeeded in breaking Harvey Dent.
- At the very end of The German, The German silently offers a cigarette to Red Leader, after both pilots have been interned by the neutral Irish.
- This is the source of Riddick's redemption in Pitch Black. He's a borderline sociopathic murderer who has been killing people all his life to escape his past and will sacrifice anyone to save himself. Carolyn Fry starts out much the same way; while not being a criminal she's willing to jettison all the passengers in the opening and tries to cope with the guilt for the rest of the movie. Riddick initially admires Fry for her "strong survival instinct" and offers her at the end to leave the planet together by threatening to leave her behind to die if she doesn't. She eventually refuses and professes her willingness to die for the others. This declared intent of self-sacrifice intrigues Riddick enough to go back with her.
- He is eventually distraught when she sacrifices herself to save him and he angrily yells that she said she would die to save the passengers, but "not for me!"
- Avengers: Infinity War: Thanos, of all people, does this multiple times throughout the film. He holds no malice to the heroes for opposing him; he understands why they don't want him to kill half the universe.
- He gives this lecture to Thor after decimating the Asgardian escape ship.
Thanos: I know what it's like to lose. To feel so desperately that you're right, yet to fail nonetheless. Dread it, run from it, destiny still arrives.
- He voices his respect for Tony Stark, just as Thanos is about to kill him.
Thanos: I hope they remember you.
- He comforts Wanda after she is forced to kill Vision to prevent Thanos from getting the Mind Stone, softly telling her that he understands exactly how she feels (because he has just sacrificed Gamora, his adoptive daughter and the one person he truly loved, earlier)...before using the Time Stone to reverse Vision's Heroic Suicide and taking the Mind Stone from him anyway.
- He gives this lecture to Thor after decimating the Asgardian escape ship.
- Avengers: Endgame reveals that Thanos has always felt this way about all the creatures he's killed and the planets he's destroyed, remarking that it's never been personal and that he considers it a Necessary Evil For The Greater Good. However, with all the trouble Earth has been giving him, knowing they were well on their way to undoing his victory, and that they even managed to kill his future self, he admits he's going to sincerely enjoy obliterating the Earth:
Thanos: In all my years of conquest... violence... slaughter... It was never personal. But I'll tell you now... what I'm about to do to your stubborn, annoying little planet... I'm gonna enjoy it. Very, very much.
- In A Song of Ice and Fire
- The Spymaster Varys berates Mr. Honor Before Reason himself, Ned Stark, for the various huge political mistakes that Ned made in attempting to be The Good Chancellor until Ned says that it was all in attempt to be merciful to innocent children. At that point Varys makes a statement that both admires Ned's integrity and weighs the cost of those mistakes, (Ned is injured and feverish while Locked in the Dungeon, his best friend was murdered, one of his daughters taken captive by his enemies, all of his men killed, etc.) where he basically concludes that no wonder other people don't try to be a hero like Ned.
- Jaime Lannister expresses sympathy for how Ned's older brother and father were executed, believing it heinous. He muses over the fact it was the Starks' cruel treatment at the Mad King's hand that was one of the reasons why he killed Aerys and yet such an act brought him the contempt of Ned Stark.
- Near the end of the Harry Turtledove series World War, Nazi commando Otto Skorzeny has a moment where he admires the bravery and skills of a couple of Polish sharpshooters sent after him. (He mentions even complimenting one on his marksmanship while handing the guy his trigger finger.) He also has a moment of pity for the city full of Jews and Poles that he is about to blow up.
- In The Bible, Pontius Pilate only reluctantly allows Jesus' execution, acknowledging that he had done no wrong by Roman laws. This has carried over to numerous portrayals of Pilate.
- In Gor book Outlaw of Gor, when Tarl returns to Gor he finds that his city has been reduced to rubble by the Priest-Kings, and a mind-altered representative of the Priest-Kings shows up to inform him that it's all Tarl's fault. But Tarl sees that the man who is being used as a puppet by the Priest-Kings is crying for him - he feels pity for Tarl, the one emotion that's forbidden in Gorean custom.
- In the novelization of the Mortal Kombat movie, Goro sadly tells Johnny Cage's friend Art that Art fought well just before killing him at Shang Tsung's command. Which makes what Shang Tsung does to Art all the more hateworthy.
- The Dresden Files: Frequently, some the villains will comment on how Harry's life as a hero has given him little to no reward. It's usually a ploy just to get Harry to join them, so Harry learns to tune them out.
- In the Hornblower episode Duty, Wolfe states that he sincerely admires Commander Hornblower. It's just that he hates everything that he stands for.
- In one The X-Files episode that takes place in a carnival, a member of the freak show wonders how Mulder can bear to be so perfectly normal in appearance.
- Despite working for Yggdrasil corporation in their behind the scenes manipulation in Kamen Rider Gaim DJ Sagara seems to genuinely respect the determination and resolve of the Beat Riders in general and Kouta in particular.
- Game of Thrones:
- Varys, like his book counterpart, expresses sympathy for Ned Stark. He notes he almost forgets that there are genuinely noble people like him in the world. However he then notes how the Crapsack World of Westeros treats them and why good people like him are so rare in the first place.
- Jaime Lannister expresses a degree of sympathy and respect for Ned Stark (despite there being absolutely no love lost between them) when he sees Ned setting himself up for a fall. He also shows similar sympathy for Ned's father and brother when he speaks of how they were horrifically executed by The Mad King.
Jaime: Poor Ned Stark. Brave man, terrible judgement.
- Tyrion Lannister as well expresses sympathy towards the Starks, Sansa in particular since she's the captive of his family.
- Varys is supportive of Tyrion in the gloomy aftermath of "Blackwater" and informs him about the attempt on his life and of his demotion.
Varys: There are many who know that without you this city faced certain defeat. The king won't give you any honors, the histories won't mention you, but we will not forget.
- On Arrow, Slade expresses this towards Moira, who sacrifices her life during a Sadistic Choice directed towards Oliver so that both of her children get to live.
- In the Supernatural episode "All Hell Breaks Loose, Part Two" (S02, Ep22), the crossroad demon says she will make a deal with Dean because she has a soft spot for him. He reminds her of a puppy.
- 24: Corrupt Corporate Executive Jonas Hodges expresses sympathy for Jack Bauer.
Hodges: I watched the Senate Hearing yesterday. And I was disgusted with how you were treated. You should be regarded as a hero, not a criminal.Jack: I broke the law.Hodges: You were following your instinct to protect your country. Just like me!
- During James Storm and Eric Young's match during the 2007 TNA "Fight For The Right" tournament, Storm accidentally hit his manager, Jacqueline, while she was trying to interfere on his behalf. It still ended up working out though, because Eric Young decided to make sure she was alright, creating enough of a distraction to give Storm the advantage. To Storm's protests however, Jacqueline gave Young a beer in appreciation afterwards.
- La Parka Jr. and Cibernético both wanted to take down La Sociedad in AAA but Cibernético and Los Bizarros, the tweeners in the angle, only slightly prioritized attacking La Sociedad over attacking Jr, to the point Jr formed his own group, El Inframundo, to defend himself from Los Bizarros. When that proved insufficient, La Parka Jr ended up joining La Sociedad itself. When Los Bizarros continued to defeat them though, La Sociedad turned on La Parka Jr as a scapegoat for their failure, causing Cibernético to finally work with him against their common enemy.
- In Cyrano de Bergerac, De Guiche, initially a villainous character, comes to feel great respect for Cyrano. He recognizes that Cyrano doesn't prosper because he never sacrifices his principles, and he (De Guiche) lives a life of prosperity because he does, and part of him wishes he had Cyrano's moral courage.
- In Antony and Cleopatra, Octavius Caesar spends most of the play bringing Antony down, but still seems to feel sorry for him; though the "Poor Antony" line can come across as either sincere or mocking depending on the direction, his open and indisputable grief when he hears of Antony's death suggests he was sincere.
- In Hamilton, the principal antagonists are Hamilton's political rivals, Thomas Jefferson, James Madison, and Aaron Burr. After an arc of songs about Hamilton's personal life, culminating in the death of Alexander's son Philip. After "It's Quiet Uptown", a heartbreaking song about grief and loss, Jefferson and Madison come back on and Madison is sobbing.
- Mass Effect and Mass Effect 3 with Saren and The Illusive Man, both stating "It's too late for me." The latter more poignant, showing genuine sadness when Shepard won't join him, when he says, "Your idealism is... admirable."
- Several of these show up in endings from the Samurai Shodown series. For example, in the second game Haohmaru's ending has his murderous rival Genjuro acknowledging the grueling fight Haohmaru had been through and being talked into sparing Haohmaru's life by Haohmaru's Love Interest, Oshizu. Later, after Haohmaru parts from Oshizu to continue Walking the Earth, Ineffectual Sympathetic Villain Gen-an, a goblin creature, says that the parting moves him to tears.
- In Undertale, the King Asgore shows reluctance in killing the seventh child, asking them to do whatever they need to before fighting him. To begin the fight, he says "Human... it was nice to get to know you... Goodbye."
- Lich sorcerer Xykon thoroughly outclasses hero Roy Greenhilt during the Battle of Azure City in The Order of the Stick and takes a certain degree of pity on him, offering to let him go off and train for awhile so they can have a decent fight later on. Roy refuses, of course, and things end...poorly.
- In The Venture Bros. The Monarch tries to break Dr. Venture with a device designed to generate mental trauma, but finds that he's already far too broken so it doesn't have any effect.
"What can I do to this guy that life hasn't already?"
- Discord toyed with this in My Little Pony: Friendship Is Magic:
- In "Return To Harmony Part Two", Twilight Sparkle is thoroughly broken, alone, and defeated, and Discord appears to gloat. When she ignores him he appears to show her sympathy and asks her to cheer up. When she doesn't he gleefully yells "YES!!!" and cackles maniacally, happy that he's broken her once and for all.
- When Discord once again causes trouble in "Keep Calm and Flutter On", he asks the duped Fluttershy to come join him in his chaos like he had with Twilight above. When she angrily refuses his friendship, he scoffs at the idea he should feel bad just because she's the one friend he ever had.... His HeelFace Turn is cemented when realising he actually feels bad for how his plan affected Fluttershy.
- Batman: The Animated Series: The episode Harley's Holiday has Harley Quinn released from Arkham after being judged sane and redeemed. Although she genuinely is, at the start, a misunderstanding whilst buying a new dressnote leads to a case of Disaster Dominoes that sees Harley being chased by the cops, the mob, and a mad general driving a tank through town. All the while, Batman keeps trying to talk Harley into surrendering so they can sort things out. This leads to this exchange at the end, after Batman finally takes her back to Arkham:
Harley: There's one thing I gotta know. Why did you stay with me all day, risking your butt for somebody who's never given you anything but trouble?
Batman: I know what it's like to try and rebuild a life. (He takes out a bag and hands Harley her dress.) I had a bad day too, once.
Harley: Nice guys like you shouldn't have bad days.
- She promptly gives him a chaste peck on the cheek as thanks... then stops, thinks about it, and gives him The Big Damn Kiss that has Robin and Poison Ivy looking on stunned, before suggesting that Batman call her later, which makes him gently chide her not to push her luck.
- Batman Beyond: Return of the Joker: Set up and then defied for the sake of Kick the Dog when the Joker finally finds out Batman's secret identity and the reason he became such. The Joker says that it's so disappointing to find out his arch-nemesis is driven by "mommy and daddy dying" that it's making him sad...
The Joker: Oh, what the hell, I'll laugh anyway!!! (maniacal, mocking laughter)