Unsurprisingly, the sad songs are quite tearjerkers.
While his behavior in "Just One of the Princes" was unacceptable, in "The Flying Crown", you can't help but feel sorry when it turns out that Hugo couldn't take the pressure of living up to his family's legacy, and he was living in the shadow of his older brother Axel, who bullies him mercilessly to get him to do so, which explains why he was such a bully.
In "Lord of the Rink", Hugo is also pressured to do manly things to avoid being made fun of, which is why he feels like he has to divide his attention to ice dancing and hockey, which stands in the way of his father's attempts to spend more time with him.
Cinderella's appearance in the pilot episode "Once Upon a Princess", telling Sofia that the amulet connects her to the princess of the past...
Though she may have only meant that Sofia's amulet calls the girls before they would become queens.
After Amber ruins Sofia's dance lessons out of jealousy, James telling Amber that he likes Sofia better than her, much to Amber's dismay. When she hears the maids say that Sofia is the prettiest princess in the palace, Amber runs back into her room in tears. While she was a Jerkass to Sofia, it's hard not to feel sorry for her.
When Sofia casts the "dancing" spell Cedric gave her, unaware that it was really a sleeping spell, she finds herself alone in the dark with no one to turn to and breaks down in tears.
Cinderella blames herself, just as much as her step-sisters, for their broken relationship.
The end of Cedric's Villain Song in "Cedric's Apprentice" is pretty depressing, what with the low, sad tone he sings it in, almost made worse by the Troubled Fetal Position he's in.
"I Belong" is more-or-less Sofia's "I Want" Song and how she wishes that everyone would accept her as a princess, even though she wasn't born into royalty.
"Blue-Ribbon Bunny" wrings as much drama as it possibly can for a show like this. Sofia wants to enter Clover in the pet contest, but he doesn't want to do any preparations such as grooming, practicing and especially not wearing a big pink bow. Sofia getting annoyed with this asks if she can take "Ginger" (A bunny in the royal zoo who was bred as a show-animal) instead. This completely crushes him, not just the fact she chose another bunny, but he starts to question their friendship as well as his own skills. To the point where you just want to hug him. Of course Sofia learns her lesson that friendship is more important than winning but still, this was incredibly tearjerking.
In "A Royal Mess", it's sweet how Sofia took the blame for her older brother playing ball inside and breaking the window, so he could go to the circus, but it only makes James sad that she got in trouble for something that wasn't even her fault. He can't even enjoy the Juggling Jesters.
"The Love We Share" (AKA "Joining Together"), sung by Ariel and Sofia in "The Floating Palace", definitely counts, because Sofia wanted to free the mermaids for so long, while Ariel wanted to free the humans for so long. In Ariel's case, this is possibly the saddest example of Disney Princess cameos to date, excluding Cinderella's appearance.
In "Four's a Crowd", it's nice that Ruby and Jade have finally become friends with Amber, but in the process, they ignore Sofia and don't even let her try to join their fun. They don't even notice how hurt she is when they teach Amber their special hand clap. You just wanna hug the poor girl.
In "Mom's the Word", the "Me And My Mom" song Sofia sings when she misses the times when she was alone with her mother.
Also counts as Harsher in Hindsight with Ariel Winter's troubled relationship with her mother, from whom she was emancipated in 2015.
As revealed in a flashback in "The Princess Stays in the Picture", a young(er) Hildegard embarrassed herself on the first day of school. It's what made the princess think she needed to be a snobbish know-it-all to be liked.
In "When You Wish Upon a Well", Amber feeling like a third wheel as Roland helps Sofia with the obstacle course.
Amber's betrayal of Sofia's trust in "The Curse of Princess Ivy". When Sofia trusts Amber with the secret of her amulet and refuses to let her wear it, Amber jealously steals the amulet for herself only for said amulet to curse her by bringing Princess Ivy to Enchancia. This betrayal leads to Sofia angrily telling Amber off for what she did, not to mention complaining about the mess when she's the one who made it in the first place. While Sofia and Amber reconciled in the climax, it's hard not to feel sorry for Sofia because betrayal can really hurt.
In "Clover Time", when Bryce Twigley comes to paint Sofia's portrait, he finds the painting Clover has painted of all the things he loves most in the world, and when Sofia sees it for herself, she says, "I didn't know he painted me, too" like she's going to cry.
"Sidekick Clio" has Clio telling Hildegard that she (Clio) shouldn't have to choose between doing what she loves and being friends with Hildegard, only for Hildy to tell her that she already did and storm out, leaving Clio crestfallen.
"Bad Little Dragon" has Vivian adopting what looks like a lonely baby dragon, and Crackle not only becomes jealous but learns that Cripsy is really a grownup and plotting to steal the castle jewels. In no time, he pulls stunts, such as eating the pies, scorching Vivian's new mandolin, and faking a burn, and Vivian immediately scolds Crackle for all of this. It becomes even more heartwretching when Crackle decides to run away. When Vivian learns of this, she realizes she was too hard on her pet. Luckily, she learns that Crispy isn't what she thought and caused all that trouble.
Thanks to Hildegard telling Sofia that Roland isn't her real father, Sofia doubts her place in Roland's heart during "Dads and Daughters Day," because she feels she is just a stepdaughter. Luckily Roland and Amber set her straight.
In the Dads and Daughters song in "Dads and Daughters Day", the princesses all sing about certain stories they had with their dads at a certain age. When it comes around to Sofia, who has to sing about her dad at the age of five, she doesn't know what to say, heavily implied to be because her biological father was already gone when she was five.
In another episode, Sofia states that she knew how to sail at the age of four. Since her father was a sailor and Miranda takes sailing lessons during the show, it can be assumed that her father was the one who taught her how to sail... which means that he had died/left very recently when Sofia was five.
In "One for the Books", Desmond finds himself unable to make any progress on Mr. P's Mystery Gardening assignment. It is already tough for him in that this task eschews the traditional book learning that he is used to. But what makes it worse is that Desmond's status as top student has made him too proud to ask for help, despite Mr. P encouraging anyone who needs help to ask for it, and Sofia trying to help Desmond understand that there's nothing wrong in doing so. Unfortunately, his frustrations and fear of failure only grow worse as he sees every other student in the class solving the problem while he continues to struggle in vain on his own.
In "Day of the Sorcerers", Sofia tells Cedric that she's angry with him for the things he's done, but mostly for him saying that they weren't friends. Despite his betrayal, she wants to believe that it isn't true, given the amount of times he's put himself in danger for her sake. Cedric himself sounds like he's on the verge of tears when he offers her a sincere apology from his cell. And of course, he later redeems himself, moving into Awesome and Heartwarming territory.
After years of kowtowing to Roland and only being able to voice his grievances in private, Cedric finally (and pretty brutally) lets the king know just why he's been plotting to overthrow him.
Roland: I never thought you were capable of something like this!
Cedric: You never thought I was capable of anything. No one did! I remember those days when your father was the king and mine was the royal sorcerer. Everything you did was the greatest thing ever. But did anyone notice when I did something right? No, they only noticed when I made a mistake.
Roland: And you made a lot of mistakes.
Cedric: So did you. And so did my sister. But neither of you could do any wrong in our parents' eyes. I on the other hand, could only do wrong. All I wanted was for someone to finally see that I am a great man...
The delivery of the last line is what clinches it; Cedric had already been bearing second thoughts about his dream of taking over Enchancia, and after he's failed and disgraced himself for all to see, he finally and soberly realizes what he's wanted for all these years.
Cedric's backstory in "Through the Looking Back Glass". When he was just a little boy, he was Misblamed for bungling a spell that permanently damaged his sister Cordelia's hair. Everyone came to consider him a bungler and even said so to his face (again, he was a child), which gave him anxiety and self-esteem issues that turned him into the bungler they all said he was. What's more, his sister and father grew apart from him as a result of this incident. When Cedric actually discovers the truth behind the incident and how he hadn't actually bungled the spell, he says the line "all these years", and his tone of voice is just heartbreaking, reflecting just how bad a hand in life this guy has been dealt.
"Ivy's True Colors" has Ivy crestfallen that Roma has the Deep Sleeps to the point where she cries, and she sings "This Feeling I'm Feeling in Me".
Chrysta being alone in her house near the end of "The Mystic Isles: A Very Mystic Wassailia," and unwrapping her present from Sofia. It moves into heartwarming territory when everyone comes to spend time with her, but still.
In "The Birthday Wish", Sofia having a horrible birthday experience is bad enough, but having to go through it 37 times so that she can get out of a magic Groundhog Day spell that can only be broken when she's truly happy, is pretty sad to say the least. She even has a breakdown.
James didn't truly appreciate being heir to the throne due to the boring tasks until he lost the position in "A Royal Wedding" when it turned out that Amber was the real heir to the throne due to being older by seven minutes. You really can't blame him for being upset—he spent his whole life thinking he was going to be king, and it all turned out to be a lie, and all because Roland botched up the law, thinking that it's the firstborn son who is heir to the throne.
Florence Henderson, who provided the voice of Grand Mum, died in November 2016 from heart failure. Not only is this the last episode where she voiced Grand Mum, but it's the last episode where Grand Mum speaks at all.
In "The Royal School Fair", the fact that Sofia is having a hard time picking out a school and everyone pushing her so hard to make her choice that she has a breakdown, throwing her tablet down and running away. A situation like this can hit home for anyone who's struggling to find a good school for them. Amber only makes it worse by picking Sofia's school for her without asking.
We finally learn what happened to Miranda's first husband and Roland's first wife; The former was a sailor and lost at sea, as we are shown Sofia looking sadly at a ship-in-a-bottle while Miranda comforts her. For the latter, we see Roland lovingly embracing his newborn twins, followed by him grieving his late wife at her deathbed.
Even worse? It turns out Roland's first wife was unable to bear children. He used his first wish in the Wishing Well to ask for children... but her body ended up not being able to handle the stress of childbirth and passed away.
What's more, prior to Once Upon a Princess, Amber and James had no idea what it was like to have a mother, which makes you understand why they were so excited to celebrate Mother's Day with Miranda in "Mom's the Word".
Remember in "When You Wish Upon a Well" when the titular well revealed that Roland made a wish prior to the series? Well, now that the first wish is revealed, it just makes that moment very depressing, especially when Roland says that the wish didn't turn out very well.
As Sofia and Minimus retreat to the Secret Library, Sofia sees Vor's conquest of the castle, and feels like all hope is lost.
Sofia: The castle! (They see the castle surrounded by Vor's dark green smoke) Vor must've gotten in! Minimus, my mom and dad! My whole family! Everyone I know is in there! Minimus: Well, we could try to save them. Sofia: How, Minimus? When we couldn't stop her the first time? Vor was right! I can't stop her on my own! Minimus: Maybe we could get more help. Sofia: There's no one left to help. There's nothing left at all. (she slumps to the ground and lowers her head)
Just like Elena, Sofia learns firsthand what it's like to be sealed away in the Amulet, being unable to do anything but watch helplessly as the people she loves suffer and her world is in danger. Fortunately, it doesn't take as long for her to get out.
Cedric and Wormwood never reconcile, with Wormwood staying evil to the end. While Jerkass Wormwood doesn't seem to have any remorse for betraying Cedric, there is clear emotion in Cedric's face and voice as he is forced to defeat and cage his long-time companion.
The series finale in general. Numerous fans were heartbroken to learn that the series was ending.