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SYFY WIRE Features

The 10 saddest moments in Pokémon history, ranked

By Rafael Motamayor
Pikachu crying in Pokémon

With over 1,050 episodes of an anime series, 21 movies and over 30 video games under its belt, there's no denying the power of Pokémon. The two highest grossing anime movies in the United States are the first two Pokémon movies. This is a franchise that through more than 20 years of existence has captivated audiences' minds with a wonderful world filled with interesting creatures you want to find and get to know, with so many adventures you could never follow them all.

Despite it being a franchise aimed towards kids starring a cute yellow rat that says "Pika Pika," Pokémon has never shied away from pulling our collective heartstrings and squeezing them to the point of traumatizing generations of fans.

Before Pokémon: Detective Pikachu finishes invading our dreams (and maybe a nightmare here and there) with live-action versions of Mr. Mime and Ludicolo, let's revisit the most heartbreaking moments in the Pokémon franchise.

10. Team Rocket says goodbye to Arbok and Weezing

If there is one constant in the Pokémon anime, it's that Team Rocket is always bad and they always lose... except in the episode "A Poached Ego!" from the Pokémon Advanced season. This is not only the first episode where Jessie and James from Team Rocket are the protagonists and heroes, but also one of the few episodes of the anime to deal with the very real issue of animal poaching.

When Jessie and James find a cage full of Ekans and Koffings, Pokémon from which their own Arbok and Weezing evolved, they try their best to free them. When they inevitably fail (because they always do), they selflessly decide to draw the attention of a poacher and his powerful Tyranitar while urging Arbok and Weezing to lead the other caged Pokémon to safety, saying goodbye to their longtime friends. It's a heartbreaking moment not only because it's the last time we see those Pokémon, but because it is Team Rocket being selfless for once.

09. Ash and his Pokémon nearly freeze to death

Despite it airing as a special episode and in the wrong order, "Snow Way Out!" is one of the most memorable episodes of the Indigo League season of Pokémon.

The set-up for the episode is that Ash gets separated from the group during a snowstorm and finds refuge inside a cave. It's impossible not to feel something after seeing Ash sitting in the freezing cold, surrounded by his Pokémon. Charmander, Squirtle, Bulbasaur, Pidgeotto, and Pikachu, who choose to stay out of their Poké Balls, settle around Ash to keep him warm, while Ash sheds a proud tear. It's a beautiful moment that reminds us that Pokémon isn't just about having cute animals fight, but becoming best of friends with their trainers.

08. Ash says goodbye to Pikachu

From the very first episode of Pokémon we've known one thing: Ash and Pikachu are meant for each other. But in the episode "Pikachu's Goodbye," Ash wonders whether Pikachu is really better off with him.

When they come across a group of wild Pikachu, Ash's Pikachu quickly tries to befriend them, even if they initially reject him for being domesticated. This is an episode that confronts the very essence of Pokémon: Is it right to capture and keep these wild creatures? Ash doesn't seem to think so, and he regrettably and painfully makes up his mind and decides to leave Pikachu behind with its kind.

Even if Pikachu ultimately decides to stay by Ash's side, with the other Pikachu lifting their tiny fists up in the air and cheering for them, it breaks the heart to see Ash think back to all the moments he shared with his faithful companion while saying goodbye.

07. Pokémon mourn their trainers

As you’ll see throughout this list, whenever Pikachu starts crying, you know s**t has hit the fan. The bond between Ash and Pikachu is the heart and soul of the Pokémon franchise, so when the climax of Pokémon: Lucario and the Mystery of Mew involves a series of blobs absorbing the main cast, causing them to disintegrate, your tear ducts will start acting up on cue.

When Ash, Brock, and May release their Pokémon and urge them to escape and leave them behind, but their loyal companions refuse and stay with their trainers. The Pokémom can only stare into blank space as the humans disappear, and as it happens, they begin crying. Despite the humans coming back to life shortly thereafter, it’s the magical Pokémon tears that pull every single heartstring.

06. Luxray freezes to death

The soft reboot movie Pokémon: I Choose You replaces Brock and Misty with new characters. The new Brock is a kid named Sorrel, who explains his tragic backstory. It involves forming a close bond with his family’s pet Pokémon, Luxray. One day, his family wasn't home, and Sorrel went out to play in the snow, but he quickly got lost and couldn't find his way back. Luxray, ever the faithful companion, sensed this and left to find Sorrel.

Because of freezing temperatures, Sorrel was unable to move, and knowing he was in danger, Luxray cuddled up next to Sorrel. The next morning, we hear Sorrel let out a gut-wrenching scream as paramedics rescue the boy but leave the frozen body of Luxray behind. It's a morbid reminder that your loved ones can leave at any time.

05. Pokémon pulls a 'Jurassic Bark'

The newest Pokémon anime, Sun & Moon, aired an episode so tragic it has been compared to Futurama's "Jurassic Bark." What starts as a cute episode about a stray Litten and its buddy, the older and wiser Stoutland, ends up being a depressing and tear-jerking episode about death and grief.

When Ash comes across Stoutland and realizes how much weight it’s lost, they rush to the Pokémon Center, where Litten cries through the glass after seeing its sick friend struggling to stay alive. This, followed by a dream sequence in which Litten chases a ghostly Stoutland who slowly fades away for good is just heartwrenching.

Oh, and this is without mentioning how the anime portrays grief in the form of Litten declining to eat or move following the death of its buddy. Why do you do this to us, Pokémon?

04. Charmander is abandoned

Barely over 10 episodes into the anime and Pokémon had already used its fantastic creatures to portray the very real issue of animal abandonment. In Episode 11, "The Stray Pokémon," we meet a Charmander that's waiting on top of a rock in a forest for its trainer. Turns out, the trainer abandoned Charmander because he thought it was too weak.

Because this franchise thrives on traumatizing children, it starts to pour rain and Ash and the group go to check on Charmander, who is still waiting, on that rock, being attacked by Spearows while holding a little leaf to shield its tail flame from the rain.

While the episode has a happy ending and begins a heart-warming tale of friendship between Ash and the little lizard, you will never be the same after watching the sight of Charmander near-death still in denial of its abandonment.

03. Goodbye, Butterfree

The episode "Bye Bye Butterfree" is probably the episode most fans will mention when asked what episode traumatized them the most. It begins innocuously enough, with Brock mentioning that it's mating season for Butterfrees and that they have little time before Ash's giant butterfly Pokémon misses out on a mate. That's bittersweet news, because after Butterfree finds a mate, it is time for Ash to let it go.

A beautiful, tear-jerking montage reminds us that Butterfree — then Caterpie — was the very first Pokémon Ash ever caught, and we relive all the happy moments they lived together. No matter how painful, Ash decides it is best to let Butterfree go to live its own life, while the original Pokémon theme song plays over Butterfree flying away.

It's been two decades since the episode aired, and most of us still haven't gotten over it. As a bonus, Charmander and Butterfree's moments were recreated in the I Choose You reboot, which condenses most of the first season into a tight 96-minute feature.

02. Clones and stones and tears, oh my!

Because Pokémon: The First Movie is simply filled with sad moments (and that's just the American version) I decided to write it all as just one point in this list. The movie may have introduced some fan-favorite Pokémon like Mew and Mewtwo, but it also gave us two of the saddest moments in kids animation in 1999 (apologies to The Iron Giant).

After threatening to kill all mankind and cloning the Pokémon of our main heroes plus some other trainers, Mewtwo orders its army of clone Pokémon to fight their originals, all without their powers. Having the song "Brother My Brother" play in the background as Pokémon beat each other senseless already pulls the heartstrings, but it is when we see clone Pikachu fight our own Pikachu, and the latter refusing to fight, that the tear ducts begin to act.

To make matters worse, not 10 minutes after this fight, Ash decides to play the suicidal hero and step right into the middle of Mew and Mewtwo's fight. He catches both of their psychic streams, which deal a critical blow to our 10-year-old hero as he collapses and immediately turns to stone.

Ask any fan who saw the movie back then and they'll tell you they still carry the emotional scars of seeing Pikachu and all the Pokémon, clone or not, cry at the sight of Ash's sacrifice. Luckily, their magical tears somehow bringing him back to life.

01. Cubone's mom

This one is one of those “fun facts” that Pokémon fans constantly talk about despite not being super explicit on the anime: the cute bone helmet on top of a Cubone’s head is, in fact, the skull of its dead mother.

It's clear in the game, but you'd think something this traumatizing for kids would never make it to the anime. Yet in the second Pokémon Origins miniseries, which follows the video games more than the anime’s story, we meet a baby Cubone in a Pokémon orphanage. The caregiver tells us the story of how Cubone doesn't trust humans after an encounter with Team Rocket, and in a flashback, we see how they try to poach Pokémon in a field, including Cubone. Before they can capture it, Cubone's mother, Marowak, tells its baby to run away while it fights off the poachers. One of the poachers raises an electrified baton, and then we cut to see Cubone crying. "Because of Team Rocket, Cubone lost its mother, Marowak."

We have seen Pokémon faint and nearly die before, but to see one of them get killed is devastating.

The views and opinions expressed in this article are the author's and do not necessarily reflect those of SYFY WIRE, SYFY, or NBCUniversal.