Top 20 Pokemon Moments That Will Make You Cry

“A Togepi Mirage!”

Goodbyes are never easy, but this one is particularly grueling. Misty spent most of the early seasons quite literally holding Togepi close to her chest. So, when it finally grew its wings, it felt like the culmination of Misty’s efforts as a trainer. Unfortunately, it also meant Togetic had to stay behind to protect the Mirage Kingdom. Despite its name, there’s no mirage thick enough to disguise the bittersweet nature of this sunset-backed farewell. It managed to be satisfying, heartbreaking, and unforgettable all at the same time. With all that, let’s just say it’s no surprise that neither Misty or Togetic leave with a dry eye.

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#19: The End of an Era

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“The Rainbow & the Pokémon Master!”

It’s no hyperbole to say that Ash and Pikachu defined a generation. Multiple, actually. But, once they achieved their goal of becoming Pokémon Masters, Ash’s journey was over. And so was his time as the lead of the series. Given everything the two brought to the franchise, nothing may ever replicate what it feels like to say goodbye to them. The show understandably dedicated a whole arc to their departure, but in the end, it all came down to Ash, Pikachu, and a vow to never stop adventuring. It’s the undisputed end of “Pokémon” as we originally know it, and if that doesn't leave you all mushy, we aren’t sure what will.

“Pokémon 4Ever - Celebi: The Voice of the Forest” (2001)

As part of a kid-friendly franchise, the “Pokémon” anime doesn’t usually tackle the idea of death. But, not only does the fourth film actually kill off Celebi, it doesn’t shy away from any of the gim implications, either. In a surprisingly bleak turn of events, there’s nothing Ash can do but sit and watch as the Mythical Pokémon shrivels in his arms. He tries everything in the book to bring it back to life, but in the end, it only makes this moment even more heart wrenching. Later, a flock of time-traveling Celebi ensured the Mythical Pokémon had a happy ending, but forgetting about its wilting corpse is a different story.

“Charizard's Burning Ambitions”

It’s a trainer’s duty to, well, train. In Ash’s case, that meant leaving his Charizard at the aptly-named Charicific Valley. Surprisingly, Ash’s decision was the easy part. Getting Charizard to agree wasn’t quite as simple, though. The trainer had to bring out all kinds of nasty insults to convince his stubborn fire-type to stay. While neither of them believed his words, that doesn’t make them sting any less. If anything, they just underline how much Ash wants his Charizard to succeed, even if it’s without him. Then, as if this moment doesn’t hurt enough, it ends with the realization that Ash can’t even bear to look back anymore.

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#16: Ash, the Pokémon Master

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"The Finals IV: "Partner”"

It took over 1200 episodes, but Ash Ketchum finally became the very best like no one ever was. And he proved it through one hell of a battle. That final stretch with Leon’s Charizard features some of the best combat the series has ever seen, partially because of how high the emotional stakes are. With his ultimate dream on the line, it’s only fitting that each of his past partners make one final appearance. But, of course, this is Pikachu’s fight to win. So, with “Pokémon’s” legacy in the balance, Ash’s starter delivered a poignant conclusion to a story over 20 years in the making.

“Pokémon Ranger & the Temple of the Sea” (2006)

On paper, this scene has no right being this impactful. It’s not the first time a trainer parted ways with a Pokémon, and it definitely wouldn’t be the last. May never even officially caught Manaphy, either. And yet, against all odds, their adieu hits just the right balance of wistful and melancholic. This closing scene owes a lot of its emotional heft to the fantastic movie that preceded it. As opposed to the usual one-off legendary, Manaphy had enough personality and screentime to make its bond with May feel honest. Although, that’s a dual-edged water-gun, since it made their goodbye hurt in all the right ways.

“Seeking Shelter From the Storm!”

In the middle of a dark and stormy night, Ash and the others think they’ve stumbled into a haunted house. However, the only thing frightening about this episode is Espurr’s harrowing journey. The Pokémon just wants to be reunited with the home’s owner, but unbeknownst to Espurr, they’ve already passed away. In a sense, the psychic-type’s entire journey serves as an evocative portrayal of denial, grief, and acceptance. None of the steps would work without the others. But, as a whole, they build toward a masterfully cathartic cemetery scene. Though, heads up: if you’re gonna watch it, be sure to have a box of tissues at the ready.

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#13: Ash’s Revival

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“Pokémon: The First Movie - Mewtwo Strikes Back” (1998)

When “Pokémon” flew to the big screen for the first time, fans probably didn’t expect to see Ash almost die. The fact it comes as a self-sacrifice doesn’t help matters, either. Suffice it to say, there’s a whole lot of crying going on in this scene, and most of it is coming from the Pokémon themselves. In fact, there’s so many tears, they end up miraculously bringing Ash back to life. To this day, it’s one of the most stunning examples of trainer-partner solidarity, ever. So much so that, by the time Ash opened his eyes again, we’d bet the Pokémon weren’t the only ones wiping away tears.

“Crossing Paths”

As a child, Jessie chose to follow ambition over love and happiness. Years later, the Team Rocket operative made sure her beloved Dustox didn’t make the same mistake. Look, ‘sincere’ isn’t a word that’s used to describe Jessie very often. But, the obvious parallels to her own backstory make her impassioned pleas feel incredibly genuine. Jessie truly believed this was the best path for Dustox. And, just to prove, she smashed the bug-type’s Pokéball so it had nowhere to return to. It’s not exactly a warm and fuzzy goodbye, but coming from Jessie, it’s the best sendoff a mon could ask for.

“Snow Way Out!”

Even in the middle of a harsh snowstorm, Ash isn’t willing to let Pikachu and the others freeze for his benefit. But, in a wholesome twist of fate, his partners feel the same way. No matter how many times Ash orders his Pokémon to stay warm in their Pokéballs, they insist on huddling with him instead. Apparently, partners who fight together, freeze together. By this point in the show, they’d all been through a lot. But, it’s this singular moment that really showed the love between partner and Pokémon. Plus, it even saved them from the blizzard. Guess they don’t call it heart-“warming” for nothing.

“Charmander - The Stray Pokemon”

As one of the most iconic creatures from the games, Charmander was always bound to have a big role in the TV series. When Ash first meets the Pokemon, it is waiting for its master who abandoned it. This immediately fills us with pity, but the truly heartbreaking moment comes later. Ash and friends see Charmander out in the rain, still waiting, even though the water will kill it if his flame goes out. Watching Ash try to convince the Pokemon to come in and seeing it refuse is sad because of how committed Charmander is. Knowing that Charmander eventually joins Ash is the silver lining!

“Just Waiting On a Friend”

In one of the stranger episodes of the series, Ash and company become trapped in a haunted house. There they encounter a Ninetails who refuses to let them leave and wants Brock to be its new trainer. They soon find out that the Pokémon is waiting for it’s master who died long ago. This is a strange but mournful moment in the show that highlights the deep connection between Pokémon and their trainers. Ninetails may he misunderstood in the episode but it’s loyalty to its trainer is clear and makes us weepy.

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#8: The Contest Winner

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“Win, Lose or Drew!”

A great aspect of Ash’s travels in Hoenn was being able to see his companion, May, compete in her own way to become a better trainer. May had worked so hard to get to the contest finals and even though she almost wins, in the end, she loses. This was a great dramatic point in the show that teaches viewers about dealing with loss. Seeing May break down after the fight is hard to watch but also great to see her react so realistically. Seeing how her friends comfort her is reassuring and makes us tear up everytime.

“Time Warp Heals All Wounds”

Pokémon is known for having some other worldly plot devices in it and this episode is a great example. After hearing about the tragic story of a girl’s grandfather passing away in an accident before her grandmother could see him again, May and Meowth are transported back in time and try to change the past. In the process, they save the girls grandfather from dying and find that the entire town is better off afterwards. This moment is hugely emotional and makes us feel both sadness and happiness because being reunited with a previously deceased relative is something we all wish for.

“A Poached Ego”

Although Team Rocket are always trying to steal Ash’s Pikachu, they have become more than just villains in the show. Throughout the series, we have grown closer to them and understood them as characters more. In this saddening moment, Jessie and James force their Arbok and Weezing to flee from a poacher and join wild Pokemon. Clearly upset by this, the Pokemon reluctantly leave as Team Rocket desperately tries to hold the poacher and his powerful Pokemon off. The expressions of Arbok and Weezing as they leave are enough to make anyone cry.

“Go West Young Meowth”

Meowth has always been a rarity in the series because he is one of the few Pokémon that can speak the same language as humans. In this episode we find out that he learned to talk for love. Meowth has always seemed to have a deeper characterization than just being a bad guy and it’s great to see that explored. It’s hard not to relate to him, even just a little bit, after seeing what he has gone through. Sadly, seeing him getting turned down at the end makes things all the sadder. Hang in there Meowth!

“Bye Bye Butterfree”

This scene is known for its tear jerking parting between Ash and his Butterfree. Being the first Pokemon Ash caught in the wild, the two had a special connection. The moment is a great blend of music, visuals and heightened feelings from the characters. Bye Bye Butterfree showed the audience that not all of Ash’s Pokemon were going to stay with him forever. It also set out how Pokemon could deal with mature themes like separation and how friends may leave each other but still care. Ash wishing Butterfree well is the perfect bittersweet moment.

“Gotta Catch Ya Later!”

Even though she hasn’t been a main character on the Pokemon TV show for over a decade, Misty is still remembered as one of its most iconic characters. Her relationship with Ash was funny, difficult and endearing. So, when she and Ash finally part ways, the audience really feels it and its hard not to get emotional. During a montage of all their moments together, we really get to see how far they have come and how they have affected each other’s lives. Although Brock also ends up leaving temporarily as well, beyond anything else, this is just a great, wholesome moment that shows the power of friendship.

“One Journey Ends, Another Begins...”

In a more recent episode, Pokemon dealt with a topic it had often shied away from in recent years, death. Ash follows a Litten that he gave food to and finds that it has been feeding an elderly Stoutland. Over the course of the episode, the Stoutland eventually passes away and Litten’s reaction to losing its friend is very upsetting. As Litten stands in the rain, calling out for its friend, its easy to see why this makes most viewers cry. A beautiful moment about friendship and dealing with loss, this episode will long be remembered.

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#1: Pikachu Leaves Ash?

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“Pikachu’s Goodbye”

The bond between Ash and Pikachu is one of the most beloved aspects of the TV series. In this season one episode, Pikachu finds a group of wild Pikachu and Ash, thinking it would make Pikachu happier, makes Pikachu stay with them. As Ash walks away from his Pokemon, we see a tear jerking montage of all the great moments the two have shared. This scene is a great example of the bond between trainer and Pokemon and also the drama between characters that fans love so much. Knowing that Pikachu and Ash are quickly reunited doesn’t make us any less watery eyed when we watch it!