The 4 saddest Pokemon episodes from Season 1 of the anime

Caution: Nostalgia avalanche incoming! These four Pokemon episodes were real tear-jerkers, so have some tissues handy.

The first season of Pokemon originally aired on April 1, 1997 in Japan and on September 8, 1998 in the United States. Each of these four episodes is from the first season, so pack your bags for a trip down memory lane. But take heed of Delia Ketchum’s advice to Ash when he first set out on his Pokemon journey, “Don't forget to change your underwear, Ash! Every. Single. Day!”

Note: This list is subjective and reflects the opinions of the writer.

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The 4 saddest episodes from Season 1 of the Pokemon anime

#4 - Episode one Pokemon - I Choose You!

Image via The Pokemon Company

This list would have a warrant out for its arrest by Officer Jenny if it didn’t include the first-ever episode. The series premiere was full of fantastic moments. From Ash getting his lifelong side-kick, Pikachu, to him stealing Misty’s bike while trying to escape a furious flock of Spearows. Of course, the most heartfelt scene is when Pikachu realizes Ash genuinely cares for him and zaps the flock away (burning Misty’s bike to a crisp in the process). Totally worth it to start one of Pokemon's most legendary friendships ever.

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#3 - Episode eleven Charmander - The Stray Pokemon

Image via The Pokemon Company

Who could forget poor Charmander? His jerk of a trainer, that’s who! Try to hold back the tears while remembering this one, otherwise you might extinguish Charmander’s flame. Ash, Brock, and Misty rush out into the pouring rain to rescue the little fella’, after hearing its trainer, Damian, flaunt about how he abandoned it.

Things weren’t so simple though, even after Ash brought Charmander to the Pokemon Center to be healed, the Fire-type was still loyal to its trainer. In the end, however, the Pokemon saves Ash and his companions from Team Rocket by using the powerful Flamethrower move. Charmander then refuses to go back with Damian and officially joins Ash’s party.

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#2 - Episode twenty-one Bye Bye Butterfree

Image via The Pokemon Company

Leave it to Brock to inform Ash about the Butterfrees' season of love that was underway as the group was traveling to Saffron City. After Ash’s Butterfree initially fails to impress the lady who catches his eye, the gang tries to give him some advice.

It seems Butterfree had what it took all along, however, because when he saves his love from the clutches of Team Rocket, she accepts him as her mate. This episode ends with Ash waving a teary-eyed goodbye to his old companion while he remembers all the great moments they shared.

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#1 - Episode thirty-nine Pikachu's Goodbye

Image via The Pokemon Company

In this episode Ash, Misty, Brock, and Pikachu have a chance encounter with a group of wild Pikachu living together in the forest. When Ash sees how happy his Pikachu is being with its own kind, he makes the tough decision that the Pokemon would be better off staying there.

Fear not though, nothing could come between the bond these two share. When Misty and Brock catch up to an emotional Ash, we see his Pikachu saying goodbye to its fellow Pokemon and leaping into the arms of its beloved trainer. Ash tears up at the end, so it’s okay to let it all out now.