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Anime and Manga
- In Axis Powers Hetalia, the American Revolution is pretty much portrayed this way. Played for Drama, the scene with the rainy battlefield where a desperate England, with his army lost, attacks, disarms but still can't shoot America, before breaking down in tears, is a famous Tear Jerker. To quote America's thoughts... "You used to be... so big..."
- In Everyone Says I Love You, there is a quick exchange between Alan Alda's character and his son over political beliefs. He playfully exclaims, "How did I end up with a kid on the other end of the political spectrum? How did I fail? Steffi, get me a copy of my will... and an eraser."
- Both versions of Freaky Friday or its many rip-offs utilize this trope but also subvert it in that in the end, it's shown that the teenagers and parents weren't quite as different as initially believed.
- Gus of My Big Fat Greek Wedding agonizes over his daughter Toula wanting to go to college, work with computers, and date and marry a non-Greek man instead of wanting to Stay in the Kitchen and become a Greek Baby Factory like all the other women in the family.
- Trainspotting: Renton's parents have this view toward him and it's justified considering he's a heroin addict. Sadly, he realizes how much they must be disappointed in him.
- SLC Punk!: Stevo's parents also seem to have this reaction when Stevo is finally able to fully rebel without any parental repercussions. It should be noted that, while he does flip off his parents and shouts "Fuck you!," he also takes the time to mention that he loves them.
- Austin Powers: Dr. Evil asks where he went wrong out loud in response to Scott Evil not living up to his father's expectations in the first two movies. They reconcile in the third movie although Dr. Evil does a Heel–Face Turn, leaving Scott as the lone Big Bad.
- Played in the most serious, dramatic, and painful manner possible in "The Force Awakens" with Han and Leia and their son, Ben Solo/Kylo Ren. They debate various potential reasons, from Vader's Force echo to the usefulness of Luke's training to the influence of Big Bad Supreme Leader Snoke. They try to bring him back home and for a moment he seems to respond to Han's plea but then cements himself in his grandfather's legacy by murdering his father in cold blood.
- Much of the focus of We Need to Talk About Kevin (and the Film of the Book) is Eva trying to work out whether she did do anything wrong during her school-shooter son's upbringing. While Eva seems to think that there was something wrong with Kevin from the moment he was born (he seemed to spurn contact and affection from the moment he left the womb), she is also well aware that she was a bad mother, and that this may have contributed to his apparent sociopathy. The question is not answered; Eva comes to no conclusion one way or the other, and the fact that she's an Unreliable Narrator means any thoughts she does have are suspect anyway.
- In Shaman of the Undead, this is the main line of tension between Ida and her parents. They had one girl as a "necessary minimum", expecting her to turn out to be a successful wizard like they are and get married to another well-born wizard, but she turned out to be devoid of magic and completely unwilling to settle down.
Live Action TV
- That '70s Show: Red is usually disappointed at how goofy and nerdy his son is.
- Eric's sister Laurie starts off as the favorite, but as the series progresses Red begins to see the strong character in Eric while becoming more and more disappointed in how the promiscuous Laurie turned out.
- Actually, Laurie was Red's favorite, whereas Kitty was intimately aware of what Laurie was really like and thus favored Eric whilst making sarcastic remarks towards Laurie's selfishness.
- Interestingly, before either was born Kitty wanted a girl but wound up with the selfish and promiscuous Laurie, while Red wanted a son but wound up with the goofy and nerdy Eric, so they both wound up favoring the child of the opposite gender because they had no prior expectations to disappoint.
- Family Ties: Alex P. Keaton was a business suit wearing Republican teenager born to hippy parents.
- 7th Heaven: The Kamdens have to deal with their rebellious, eldest daughter.
- Robin's dad on How I Met Your Mother tried his best to raise his kid up to be just like him... despite being a girl. He was more than upset when he caught her kissing a boy for the first time.
- George and Angie on The George Lopez Show feel this way about Carmen, especially after she runs away and becomes a groupie for some rapper.
- The Pinkmans (Jesse's parents) spend pretty much all of their time embodying this trope in Breaking Bad. As Jesse's mom says to him at one point (while throwing him out of his house): "Why are you like this?".
- This is what drives I Hate My Teenage Daughter.
- Invoked in The Suite Life of Zack and Cody episode "The Fairest of Them All" as a throwaway gag in which a girl named Tyreesha (the real one; as soon after this incident Cody gets Dragged into Drag entered into a child beauty pageant) angrily lets her Stage Mom know she wants to go to science camp instead of another pageant; leading to Tyreesha's mom using the trope name verbatim.
- The Beatles' "She's Leaving Home", on the third refrain:
She (What did we do that was wrong?)Is having (We didn't know it was wrong)Fun (Fun is the one thing that money can't buy)
- In Nerf NOW!!, a father is horrified to discover his son is a casual gamer! He's later relieved when he sees him playing a game with a Touhou character.
- Played with in this comic on DeviantArt.
- In Sabrina Online, the same concept used in the DeviantArt comic is applied to one of the main characters - Sabrina's boyfriend. His parents are ultra-liberal flower-child hippies, and extremely open-minded — and he rebelled by becoming a perfectly straight-laced IT graduate, working tech-support for Microsoft.
- In The Adventures of Dr. McNinja, the good Doctor's parents have this problem with him. Mitzi McNinja doesn't know how to raise ninja children, having become one by training, and Dan McNinja was never taught this, as it's supposed to be the mother who does this. They tried to teach him via Batman, but instead of a ruthless killer, they raised a vigilante doctor.
- Played for Drama in Worm, where Taylor's father Danny-an honest man from a working-class family who did his best to raise her alone after her mother's death-wonders what he did wrong to make his only daughter turn into a ruthless supervillain with an iron grip on the city's underworld.
- This is parodied in a sketch in a later ASDFMovie, where an officer brings a boy home and explains that he was caught "doing homework". The mother screams the singular variant of this phrase in horror.
- Moral Orel: Played straight on the [adult swim] show with a heavy case of Cerebus Syndrome. This is also a case in which it's seen as a very good thing that the kid will not end up like his parents.
- American Dad! devoted an episode on Francine and Stan figuring out what they did wrong with Hayley by cloning Steve and experimenting with parenting styles.
- It's eventually revealed that Francine's parenting alone would turn Steve into a lazy, slovenly, spoiled brat, whereas Stan's parenting alone would turn Steve into a cat-killing sociopath.
- On King of the Hill, most plots involving Hank and his son Bobby will take a turn through this trope. Most of the episodes end with Hank learning An Aesop about accepting that his son's talents and interests are different from his, then Status Quo Is God will kick in and they get to recycle the plot with a different disappointment of Bobby's.
- Finally averted in the Grand Finale when Hank and Bobby bond over Bobby's talent for grilling.
- A cartoon in Rocky and Bullwinkle featured a pair of parents who are jesters/clowns who has a son who wants to be a knight. Even the father flat out ask what did he do wrong.
- Dick Dastardly asks this in the Wacky Races episode "Race To Racine" after Muttley sabotages him instead of the intended victims the Ant Hill Mob.
- Subverted in an episode of Beetlejuice where B.J. and Lydia are involved in a road race with their car Doomie. Scuzzo and Fuzzo set a booby trap along a short cut, but Doomie refuses to take it in spite of B.J.'s wishes. "Where did I go right?" B.J. asks.
"Where did we go wrong...? This trope was supposed to be like me, the Self-Demonstrating Article!"