5 most heartbreaking Pokemon episodes of all time, ranked

The mainline Pokemon anime following the adventures of Ash Ketchum, his trusted Pikachu, and their friends brought plenty of good times and heartwarming moments along with it. However, not everything was sunshine and roses, as the characters and creatures in the anime often had to experience emotionally downtrodden moments that surely broke the hearts of a few fans.

Some of the most well-known Pokemon anime episodes are also those that left an emotional impact on watchers. Saying goodbye to good friends, losing loved ones, and even themes of neglect and abuse have appeared at times in the series, reaching fans to their core.

With Ash and Pikachu's adventures finished for now, it doesn't hurt to rank some of the most heartbreaking episodes of the anime of all time.

Note: This article is subjective and the ranking reflects the author's opinions.

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Ranking the five most heartbreaking mainline Pokemon episodes of all time

5) Sabrina's Isolation (Haunter versus Kadabra)

Sabrina's powers made her a capable gym leader but devastated her family life (Image via The Pokemon Company)

In the original Pokemon Indigo League series, Ash came face to face with Sabrina, the psychic gym leader of Saffron City. While she proved to be incredibly capable thanks to her psychic powers allowing her to bond deeply with her Psychic-type Pocket Monsters, her powers were revealed in "Haunter versus Kadabra" to have derailed her childhood and her relationship with her family.

Due to her untrained psychic abilities in her youth, Sabrina inadvertently turned her mother into a doll, causing her father to flee in fear of her and leading Sabrina to split the joyous and callous sides of her personality. Fortunately, Ash and Haunter were able to make Sabrina laugh and bring her back to her full self.

While Haunter versus Kadabra ended on a positive note, Sabrina's upbringing and isolation made it clear that all she really wanted was a warm and loving life which she lost early on in her youth.

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4) Espurr Waits for a Friend Who Never Arrives (Seeking Shelter from the Storm!)

This XY series episode knew how to tug at the heartstrings (Image via The Pokemon Company)

In the Pokemon XY series, Ash and company came into contact with a haunted house inhabited by an Espurr, who had developed a bond with an elderly woman named Lacy who owned the house and took care of the little Psychic-type creature. Espurr waited for ages for Lacy to come home, but Ash and his friends discovered that Lacy had passed away and that Espurr was waiting in vain.

Any story of an animal, fictional or otherwise, waiting for its owner in vain is heartbreaking. Fortunately, this episode had a bittersweet but slightly happier ending. The house's new owner Elise offered to drive Espurr to Lacy's grave to lay a flower, and also offered to take Espurr in to live with her as she renovated the house and brought it back to life.

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3) Ash Nearly Releases Pikachu (Pikachu's Goodbye)

Ash and Pikachu nearly split early on in the anime (Image via The Pokemon Company)

Any Pokemon fan who has seen the totality of the Indigo League season knows episodes like Pikachu's Goodbye and Bye-Bye Butterfree well, as they were among the most emotional in the entire anime. While Bye-Bye Butterfree is certainly tragic, the hour-long Pikachu's Goodbye special nearly saw Ash release his first companion and leave them behind.

During their travels in Kanto, Ash and his friends discovered a group of wild Pikachu, and Ash realized that Pikachu seemed occupied with its wild counterparts and enjoying time with them so much that it wasn't listening to Ash. This led the latter to believe that despite the bond they'd shared and the obstacles they'd overcome, it would be better to release Pikachu so it could be with new friends.

As the sun rises and a broken Ash aims to leave Pikachu behind, Pikachu says goodbye to its wild friends and returns to Ash, refusing to be anywhere else but at his side. It's a heartwarming ending, to be sure, but involved a lot of emotionally tragic moments in the lead-up. For fans who watched the episode live, the prospect of Ash and Pikachu separating was devastating.

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2) Ash Saves a Neglected Charmander (Charmander - The Stray Pokemon)

Ash's Charmander was once neglected to the point of near-death by its previous trainer (Image via The Pokemon Company)

Unfortunately, many Pokemon trainers are far from kind to their companions. Ash and company learned this the hard way early on in their Kanto adventures, finding a sickly Charmander who refused to accept help, as it waited for its trainer named Damian, who had in fact abandoned it for being "too weak." A rainstorm broke out, but Charmander refused to move, still waiting despite the danger.

As Charmander clung on to life with its tail flame nearly extinguished, Brock, Misty, and Ash managed to finally rush it to a Pokemon Center for treatment. Despite making a full recovery, Charmander returns to its post to wait for Damian, unwilling to accept the fact that it was abandoned. A showdown with Team Rocket ensues, and Charmander saves Ash and his friends from one of their traps.

Damian finally returns, only to reveal that abandoning his Charmander toughened it up and that he would take it back now. However, Charmander refuses, and it teams up with Pikachu to attack Damian and chase him off. In the end, the Fire-type starter Pokemon agrees to be caught by Ash, realizing that it deserves a trainer capable of much more love and compassion.

This episode can still be a tough one to watch, as Charmander is clearly suffering abuse but is too attached to Damian to realize it at first. Fortunately, the episode ends on a high note, and Charmander would go on to grow and evolve, becoming one of Ash's most stalwart companions every step of the way.

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1) Fans Say Goodbye to Ash and Pikachu, For Now (The Rainbow and the Pokemon Master)

Ash and Pikachu's journey may not be over, but fans had to say so long in this episode (Image via The Pokemon Company)

After winning the World Coronation Series, Ash and Pikachu returned to their home in Pallet Town. Ash's rival Gary asked him what was next on their journey seeing as Ash and Pikachu had become World Champions.

Ash decided that the true mark of a master is the ability to befriend any Pokemon, thinking back to the Latios he had encountered on his journey who had helped him but didn't befriend him. Ash and Pikachu decided to leave Pallet Town once more to parts unknown, chasing a rainbow mirroring the one they saw from Ho-Oh at the very beginning of the adventure.

While the episode ended optimistically, fans had to say so long to Ash, Pikachu, and all of the memories they made together over the anime's cumulative 26 years of airing. It marked the end of an era for many people who grew into adulthood with these characters, and while Ash and Pikachu may return in the future (maybe in the Horizons series?), saying farewell after such a long time was a lot to deal with.