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Anime & Manga
- In Durarara!!, Kadota's gang are devastated when they find out their friend Kaztano has been kidnapped, but none so much as Togusa, who even claimed he couldn't go on without the man. No one can be there for Togusa like Kaztano. Why? Because Kaztano was his source for sold-out, front row tickets to see Idol Singer Ruri Hijiribe.
- Done by America in Axis Powers Hetalia. When England 'dies' in the hospital after an accident involving the panjandrum, America gets teary eyed and tells him he can't go because he owes him a 'crap-ton of money'.
- One Garfield strip had a spider introducing Garfield to his "big" brother. After Garfield casually smashes him, he says "Hey! He owed me money!"
Films — Live-Action
- In Scary Movie, one girl is outraged to find a fellow student has been murdered... because she planned to cheat off said student's test that day.
- In Pyramids, one of the surviving student assassins mourns the one who didn't make it, noting, "He still owed me money".
- In A Hat Full of Sky a shopkeeper is horrified to see his wizard assistant turned into a frog and a big, pink, gloopy blob:
Shopkeeper: Please, please turn him back! I could never get a real wizard for what I pay him!
- In an episode of Happy Endings, Max comes in after just leaving his hairdresser's funeral. He quickly says "the real tragedy is I need a haircut and I have no one to go to!"
- In the first episode of Red Dwarf, Dave Lister's first reaction when he finally gets that Everybody's Dead, Dave and is told that he's three million years in the future is "Three million years?! I've still got that library book!"
- "Weird Al" Yankovic's song "Why Does This Always Happen to Me" is all about this, complete with $5 reference. A news flash comes on to tell about a devastating earthquake, and he mourns the fact that he was recording The Simpsons and will have to do it again. His friend dies in a traffic accident, and he mourns the $5 the friend owed him, and that he'll be late to work now. He stabs his boss, and mourns the knife, which broke and will never be as sharp again.
- "Superman" by Atmosphere. In the song Slug one day discovers he has superpowers. While walking down the street he runs into two friends of his. He goes to give one of them a fist-bump but ends up killing him accidentally with his super strength. The other friend, heard in the background, is heartbroken and laments "Why you gotta squish my friend, dude?...That dude owed me, like, five dollars. Why you gotta kill him?"
- In Borderlands you often get this reaction from NPCs when you break bad news to them. For example when you tell Scooter that T.K. (a Cool Old Guy you meet in the first town) is dead, he angrily laments that he never returned his tools.
- In Dragon Age II, Merrill misses the Qunari after they commited a massacre in Kirkwall and left, just because they "were easy on the eyes".
- Homestar Runner plays this straight in the Strong Bad Email "army", when "Col-o-nel" Homestar laments his fallen soldier Frank Bennedetto (a popcorn popper):
Homestar: Don't you die on me, Bennedetto! Not on my watch! Don't you give up! You never gave me the five bucks...
- In Alternate Reality Dragon Ball Z, Krillin gets in tears whenever Vegeta dies. Because he was carrying his borrowed iPod.
- After Sparadrap's pets were killed in Noob, deeply saddening her Man Child guildmate in the process, Gaea's apparent sympathy reaction turned out to be along the lines of "Darn, one of my potential revenue sources just got destroyed".
- This piece of Transformers Prime fanart - Knock Out is upset when he hears about Breakdown's death, not because he cared about Breakdown, but because he now has to do actual work instead of sneaking off to race.
- The Futurama episode, The Sting, has Fry sacrifice himself to save Leela, causing Bender to be devastated over his friend's death:
Leela: Fry? He's... he's dead!
Bender: Oh, who will make Bender waffles just the way he likes them now?
- In an episode of Archer, Archer's fiance has just performed a Heroic Sacrifice by tackling evil cyborg Barry off a building. She dies, Barry is just fine, and Archer is in tears over this senseless tragedy. So is Doctor Krieger; they landed on and crushed his beloved van.
- In South Park, after Kenny is Killed Off for Real, the boys discover that he has the winning ticket to a candy store shopping spree, so they decide to build a ladder to heaven in order for him to give it to them. But when adults ask what they're doing they don't mention the candy part, they just say they want to see Kenny again.
- In the SpongeBob SquarePants episode "Neptune's Spatula", SpongeBob is about to be taken to Atlantis to be King Neptune's top fry cook after beating him in a contest. This would mean separating SpongeBob from his friends. Mr. Krabs is saddened not because he lost his best fry cook, but because he bet on King Neptune.
- In Gravity Falls, the (incredibly old) mayor dies, and Shandra Jimenez breaks down and cries over the rush of emotion caused by having actual news to report on for the first time in ages.