We know that Evil Feels Good. So, it's also natural that evil people can get nostalgic for times that felt particularly good, such as an especially fun victim or a favorite city you destroyed. Sometimes the character does it in such a way that it would be cute if not for the monstrous deeds being talked about.
Most commonly, this is done with a Serial Killer thinking about their kills, a Blood Knight recalling a Worthy Opponent, with the villain intentionally trying to hurt or provoke a hero they might be talking to, or to show the villain having an attachment to a victim such as a Villainous Crush or a touch of Lima Syndrome.
Would You Like to Hear How They Died? and the Post-Rape Taunt are common parts of this. Contrast But for Me, It Was Tuesday, where the villain doesn't remember their victims. Compare and contrast Antagonist in Mourning. Can be an excellent Establishing Character Moment, particularly if a character is meant to be established as Ax-Crazy. See also Writing About Your Crime, when the past atrocities are committed to paper instead.
- In Tiger & Bunny three criminals sharing a jail cell swap stories of their misdeeds, one of them remarking that he loves kidnapping, because you can get a bunch of money and then kill the kid afterwards. They immediately then get incinerated by Lunatic.
- In Fullmetal Alchemist, during his interrogation Barry the Chopper talks about his various kills this way, reminiscing about how beautiful the moonlight on the pools of blood was, treasuring the memories of such halcyon days. He also instantly spots the one bogus incident they mentioned to test him.
- Generally averted with Death Note's Villain Protagonist Light, who often seems completely unconcerned with his victims' identities beyond their being Acceptable Targets and/or being convenient to kill... However, he does seem to do this quite a lot in reference to one particular victim during the series' second half.
Light: In the end, L is indeed the greatest detective on earth...
- Bleach: Mayuri reveals to Uryuu that he had studied the Quincies by launching into a long speech about all the things he did to the Quincies he'd captured in order to study responses to mental and physical stimuli. It's a speech that reveals just how far down the road of Mad Scientist he's willing to go For Science!.
- In K, the Colorless King appears in the cell where Mikoto, the Red King, is being held and taunts him about the murder of his closest follower, Totsuka. He then goes on to say he'll kill all of Mikoto's followers, one by one, and make him watch.
- A typically creepy issue of Swamp Thing has a Serial Killer who calls himself the Bogeyman and remembers his victims by number...and their eyes. Every time he hears a number, the panel shows a disembodied pair of eyes and his description of same.
- In The Sandman, an imposter Bogeyman at a "Collector's Convention" is found out when someone blurts out a number and he doesn't immediately talk about eyes. Things do not go well for him afterwards.
- In an issue of Uncanny X-Men around the 200's, Selene is confronting Rachel (Phoenix) because Selene killed a man who was helping Rachel, and Selene taunts her by pointing out that she knows all about the man she killed while Rachel doesn't even know his name.
- The Judge Dredd story "Young Death: Boyhood of a Superfiend" serves as Judge Death's Origins Issue. It's basically one long use of this trope as Death, being interviewed by a terrified journalist, happily recalls all the people that he gruesomely murdered during his long career of killing every living thing.
- Les Innommables has a pair of panels where the ghosts of Chinese victims are surrounded by fire, then cut to Colonel Lychee, who's dozing happily at the memory.
- Robin Vol 1: Sir Edmund Dorrance starts describing in loving detail the way he killed Clyde Rawlins' wife and children while beating him to death, and the last words Rawlins hears in life are Dorrance saying the only thing he regrets about the whole affair is that his blindness means he won't be able to actually watch Rawlins himself die.
- Harry Potter fanfic Aspirations has Bellatrix LeStrange remembering she used to pleasure herself in Azkaban with the memory of breaking her father's skull with a crowbar.
- Hivefled has a sidechapter where the villain couple have sex while discussing what they did to previous victims and what they plan to do to the rebel gang when they find them.
- In Shadow Of The Valley Light and Ryuk wax nostalgic about past kills.
- In the second chapter of Old West, set one year after the ending of Rango, Rattlesnake Jake remembers with sadistic satisfaction how he killed Tortoise John for his betrayal.
- Common Sense: A non-lethal and non-Ax-Crazy version: one of Team Rocket's favorite ways of Holding the Floor for their schemes and Draw Aggro from Ash Ketchum is to smugly remind him of the many (and that is many) defeats he's had to them throughout the story.
- In Rob Roy when Rob and Cunningham finally meet face to face, Cunningham teases Rob about how good it felt to rape Rob's wife. "Your wife was far sweeter forced than many are willing."
- In Gangs of New York, Bill Cutting considers Priest Vallon a Worthy Opponent and does an Antagonist in Mourning type of celebration of their fight every year.
- Hannibal Lecter seemed to really enjoy that memory of the census worker whose liver he ate with fava beans and Chianti.
- The Joker does the Would You Like to Hear How They Died? version in The Dark Knight.
Do you want to know why I use a knife? Guns are too quick. You can't savor all the ... little emotions. In ... you see, in their last moments, people show you who they really are. So in a way, I know your friends better than you ever did. Would you like to know which of them were cowards?
- In The Princess Bride, while talking with Buttercup, the Man in Black tells her how Westley pleaded for his life before he killed him. Here it's used in a more respectful way since the Man in Black hints at being moved by Westley's sincerity and devotion. Ultimately subverted in that the Man in Black did not, in fact, kill Westley...he is Westley!
- Con Air. About midway through the film, convicted serial killer Garland Greene strikes up a conversation with Cameron Poe during which he happily recounts how he once killed a girl, then drove through three states while wearing her head as a hat.
- In Return to Cabin by the Lake, Stanley Caldwell recalls Kimberly, his last successful victim before his crimes were found out, quite well. He relays to Allison, a curious scriptwriter, that she gave him "a good fight" and clawed at his arm as he daydreams about Kimberly.
- Judge Doom from Who Framed Roger Rabbit gives Eddie Valiant a truly terrifying version of Would You Like to Hear How They Died?:
Remember me, Eddie? When I killed your brother, I talked JUST...LIKE...THIIIIIIIIIIIS!
- Thrax the virus does this in Osmosis Jones, complete with DNA bead souvenirs and the twist that he's gotten faster with each victim. His endgame is to kill a human in 48 hours and set a record, ensuring he goes down in medical history.
- El Indio of For a Few Dollars More sometimes listens to the chime from his pocket watch and reflects on its previous owner, a young woman (bounty hunter Col. Mortimer's sister) whom killed herself with his gun after he murdered her lover and raped her. He wistfully dwells on her as if she were "the one that got away," a touch of humanity that ironically makes him seem even more loathsome than if he were recalling his evil deed with the sadistic glee of a Card-Carrying Villain.
- In the first book of the Sword of Truth series, the Big Bad is remembering a girl he took to his bed, and how she laughed at his scars. Since it happens during a situation when he must smile to another, he shifts to recalling what he has done to her in response.
- In King Solomon's Mines (where Allan Quartermain got his start) the Zulu warrior Umslopagaas says that he wouldn't mind meeting and talking to some of the people he had killed in battle. In this case, it isn't to show that Umslopogaas is evil but that though he is a Blood Knight he is also an honorable Proud Warrior Race Guy who respects a Worthy Opponent.
- Discworld's Carpe Jugulum:
- The vampire Count and Countess Magpyr reminisce about their honeymoon:
- Inverted by the Old Count, who decides to reminisce about some former Worthy Opponents who had killed him over the years as well as one of his intended victims (and her very shapely neck) in front of their children and grandchildren.
- In Hannibal, Mason Verger reminisces about a Christian camp he attended and his fellow campers, some of them disadvantaged youth who "would do anything for a candy bar" which allowed him to molest them. This is meant to mark him out as an Asshole Victim of Hannibal Lecter's and later of his sister Margot's.
- In The Two Princesses of Bamarre, the dragon Vollys treats her prisoners as "guests" before eating them, letting them live longer with a system of giving and taking away pieces of treasure from her hoard for entertaining her. She reminisces about several of her previous victims fondly, talking about them like they were old friends and mourning the fact that she got bored and killed them. In return, the protagonist Addie later regrets having to kill her to escape.
- In the Warrior Cats field guide Battles of the Clans, Tigerstar remembers how fun it was when he killed Redtail.
- Chiswyck's weakness for this trope leads Arya to contrive his assassination in A Song of Ice and Fire; his bragging about his band's rapes and murders proves a little too much for her.
- In Harry Potter and the Deathly Hallows, Harry's last-minute escape from Voldemort in Godric's Hollow triggers a Through the Eyes of Madness vision where Voldemort recounts the night he killed Harry's parents.
- In The Jungle Book story "The Undertakers", a jackal, adjutant stork, and mugger crocodile chat on a riverbank. The crocodile reminisces about the various humans he's eaten over the years.
- In the above quote, Michael Westen from Burn Notice is deliberately using this trope (and playing up the image Russians have of him as the CIA's version of the Boogeyman) to speed along an interrogation by freaking out the guy he, Sam and Fi are interrogating.
- Spike from Buffy the Vampire Slayer is quite fond of discussing and reminiscing about the Slayers that he has killed. During his "weepy drunk" phase post-Drusilla breakup, he remembers killing a homeless man on a bench with her...while Buffy and Angel listen in disgust. Post-chip, he tells Dawn a Ghost Story about him killing an entire family.
- Parodied and subverted in Veronica Mars.
- The Kids in the Hall, naturally, play this for laughs with a group of friends gathered to memorialize their dead buddy. Turns out they killed him, of course.
"It really makes you think about the fragility of life."
"Not really. Remember how he struggled at the end?"
- Subverted in The X-Files episode "Paper Hearts", where the villain of the week tries to convince Mulder that it was he who kidnapped and murdered his little sister by describing her last moments. Mulder eventually calls bullshit and is right: the bad guy wasn't Samantha's kidnapper, just a jerkass.
- On The Mentalist, a man claims to be the Serial Killer Red John and tries to prove this by telling Patrick Jayne how nicely Patrick's wife and daughter smelled right before he killed them. However, it does reveal he's close with the actual Red John since he couldn't have acquired these specific details otherwise.
- George Marks of Cold Case is fond of this.
- The Twilight Zone (1959): In "Deaths-Head Revisited", the former SS officer Gunter Lütze returns to Dachau after 17 years in South America to reminisce about all the suffering that he caused there.
- In the Being Human episode "Though the Heavens Fall", MacNair attempts to preface killing Herrick with describing all the vampires he has killed. Taking Herrick on a trip down memory lane proves to be a very bad idea.
- Law & Order: Special Victims Unit features this in the episode entitled "Quarry." The team believes they've unearthed another victim of a convicted murderer and pedophile. When presented with a slew of baseball caps that belonged to the victims (he had kept the caps as "mementos"), the man is able to recall the full name of the corresponding child, along with the exact date he committed the crime, after giving each hat a momentary sniff. It's just as creepy as it sounds.
- Liar: After his mask slips, Andrew starts talking fondly about how he raped not only Laura but previous women in private conversation with her, to her utter horror. Not only that, but he video-taped each rape, and regularly views the recordings again for his enjoyment.
- Kamelot's song The Zodiac is inspired by the Zodiac Killer, and in the lyrics, he reminisces about breaking the neck of a woman.
- "The Litany of the Slain" by GWAR.
- Spike Jones' parody of "My Old Flame" presents the song sung by Paul Frees (imitating Peter Lorre) as a psychotic killer who is trying to remember which one of his victims the song is about.
"My old flame / I can't even think of her name / (beat) I'll have to look through my collection of human heads."
- In Portal, GLaDOS is quite happy to talk about forcing you to kill Companion Cube
- Invoked by Kefka in Final Fantasy VI:
Kefka: Say, remind me to show you my Magicite collection someday! You might see a few familiar faces!!!
- Explained: Magicite crystals are the dead bodies of magical beings, whom Terra was born amongst.
- At one point in Borderlands 2, Handsome Jack will call you to complain about how you just aren't giving up, which somehow segues into him reminiscing about his assault on New Haven, during which a man stupidly tried to attack him with a spoon. So he scooped out the man's eyes. With the spoon. While the man's children watched.
- An odd example in Hitman (2016) where there's a rumor that Jordan Cross has a recording about the night in which his girlfriend Hannah died. He does have a recording, but he's wracked with guilt over her murder which he is responsible for.
- In El Goonish Shive, Not-Tengu talks about the previous time he created a mind controlled congregation while going on a Motive Rant.
- Jack Slash, a superpowered Serial Killer who leads a band of the same in Worm, does this a lot, recalling the numerous and inventive deaths and/or Fates Worse Than Death that he and his group have inflicted upon their victims in order to unsettle and disturb his enemies.
- In There Will Be Brawl, Kirby particularly enjoys taunting Luigi with his murder of Daisy: "I can only imagine how you must have felt...when I ate your princess, I wore her head like a hat and danced through the streets..." Fitting because he is directly inspired by Hannibal Lecter, he enjoys messing with Luigi, and doing just that was most of his point in instigating the series.
- Jojos Bizarre Adventure Abridged has J. Geil go on about this while bragging about killing Polnareff's sister.
I raped her, then I killed her, then I dressed her up as Liza Minelli, then I raped her again. I know, I'm f***ed up like that