Even a book series and TV show about a kid as horrid as his nickname indicates can get really sad at times.
- Henry's whole family and home life is actually pretty depressing when you think of it.
- Henry is horrid, as his name implies, but he is implied to be despised by his family. He rarely gets anything nice from his great-aunt because she's very senile, nobody at school likes him, and it becomes worse when he eventually goes from being an obvious culprit to a complete scapegoat. There's also the implication that he only acts horrible because he's sad and lonely.
- Peter is arrogant and spoilt, but try imagine having a brother like Henry, who constantly bullies you day and night. It doesn't help that Henry actually tried to get rid of him as soon as he was born.
- Throughout the series, Henry's parents are implied to be so ashamed of having Henry as a son, that they completely dote on Peter and ignore Henry's needs most of the time. There were some instances where they distance themselves from him in public and even pretend he isn't their son.
- Prissy Polly and Pimply Paul's marriage appears to pretty rocky and complicated. Polly never stops bossing people around or thinks about how others might feel if she only gets her way and Paul is a very hardworking guy, but people are always disrespectful towards him (even his own wife). The only thing keeping them from a divorce is their daughter Vera. It doesn't help that their wedding was totally ruined by Henry.
- The scene in "Christening Crisis" where Polly understandably panics and cries over her baby disappearing.
- It may have been an Imagine Spot, but the one in "Horrid Henry's Hike" where Henry imagines what might happen if mutated chickens ate him involves Henry's family carrying his coffin with (presumably) Ms. Battle Axe, Moody Margaret and Rude Ralph following. Dad suddenly begins crying about how stupid they were for not listening to Henry, and Mum vowing not to eat an omelette ever again as a result.
- The episode "Where's Fluffy?" can be upsetting to anyone who ever lost a pet.
- The episode "Horrid Henry and the New Best Friend" actually is a big heartbreaking one for Henry. He falls for the new girl, Nasty Nicola and actually lets his guard down to impress her. When she appears to return his feelings, it is soon revealed that she was just playing with his heart so she could frame him for many crimes and get expelled. Had Brian and Peter not intervened, her plan would have worked.
- The real heartbreaker here is that Henry seemed to truly love her and when he found out his true love was just a Bitch in Sheep's Clothing, he seemed truly crushed and heartbroken. It doesn't help that Henry did not act horrid at all in the whole episode.
- The ending to "Horrid Henry's Unhappy Day", where Margaret makes Henry her servant and posts a humiliating picture of him online even though he never did anything to her. And then the episode just ends there!
- The scene in "King Henry the Ninth" when Henry feels like he isn't special or meaningful after realizing he isn't a descendant of royalty.
- The YouTube short film "Horrid Henry and the Groovy Grandma" is this, as it tackles the concept of loss through his maternal grandmother who passed away when he was very little according to his mother.
- His mother sheds a few tears during the short.
- She was also one of the few characters to be fond of Henry, even if she didn't get to know him for long.
