Where Did We Go Wrong?

New parents are usually as happy as can be. They look forward to raising their kids as idealized versions of themselves, or at least copies of themselves. It is not bad parenting; parents want their kids to share their cherished values and ideas, and avoid the same mistakes they made growing up.

That's not what happens here.

These kids ended up having their own views of how the world works. For better or worse, they don't share their parents interests, they don't want to enter the same careers, or worst of all, they may not share their parents' political or religious views. This leads the parents to wonder, "Where did we go wrong?".

This trope is Played for Laughs as often as it's Played for Drama. Usually, neither party is shown to be to blame but rather, both share it in one way or another.

Classic set-ups include a girl with a domineering Stage Mom, or a son being forced to hunt deer in a Manly Men Can Hunt scene. In more dramatic works, a rebellious child might end up being downright criminal.

Very common in sitcoms.

Compare this to I Have No Son. May result in Why Couldn't You Be Different?. Pretty much the attitude of the "Well Done, Son" Guy's father.

Examples of Where Did We Go Wrong? include:

Film

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.
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.

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.
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.

Webcomics

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.
In Sabrina Online, the same concept used in the Deviant ART 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.
Played with in this comic on Deviant ART.

Western Animation

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.

Real Life

Disturbingly, the parents of the Columbine Killers had no idea what their boys were up to and were at a loss about what they did.
Lionel Dahmer was certainly at a loss for his son Jeffrey's horrifying urges.
It's quite common for children raised in highly conservative families to grow up with the opposite viewpoints of their parents.
This can happen to children raised in highly liberal families too.
- A joke my father used to tell me was that kids in our very liberal town would rebel as teenagers by combing their hair and voting Republican.

"Where did we go wrong...? This trope was supposed to be like me, the Self-Demonstrating Article!"