The saddest Pokémon episode isn't the Butterfree one

When it comes to cartoons and anime that scarred us for life as children, Season 1, Episode 20 of 1997's Pokémon often comes into the conversation. Titled "Bye-Bye Butterfree," the episode sees Ash learn that once Butterfree reach adulthood, they mate for life and fly off into the sunset together, never to return. Don't get me wrong, the episode is definitely a bit of a tear-jerker, though for me, most of that comes from watching poor Butterfree repeatedly try to woo a mate, only to be met with repeated rejections.

Butterfree spends a lot of time with tears in its gigantic eyes, making sad little noises that sound a lot like the noises made by Piano-chan in Sanrio's various anime series. It eventually manages to impress its bewinged mate by freeing a group of Butterfree that have been captured in a huge net by Team Rocket, and bids goodbye to Ash in a moment that is clearly meant to tug at the viewer's heartstrings.

I enjoyed this episode as a kid, and still enjoy it as an adult. But I've always found Butterfree's goodbye scene to be unintentionally hilarious, and that’s mainly because it features some flashbacks to the adventures Ash and Butterfree shared up to that point in the series… including their first meeting (which took place when Butterfree was still an un-evolved, silly looking Caterpie) and Butterfree's first evolution (into the even sillier-looking Metapod). It's a great episode, I've just never found it especially sad.

The episode that does hit me right in the feels comes later in the season. Episode 36, titled "Pikachu's Goodbye," is way more of an emotional gut-punch. It's actually got a similar setup to the Butterfree episode — Ash and Pikachu stumble across a group of wild Pikachu frolicking in the forest, reminiscent of the flock of wild Butterfree they find in "Bye-Bye Butterfree." Naturally, Pikachu is pretty curious about this little group of Pokémon who look and behave just like him.

Initially, poor Pikachu suffers rejection from the group, but a younger Pikachu eventually approaches him, gives him a sniff, and the two shake tails. After that, the group of wild Pokémon welcome Ash's Pikachu with open arms… until Ash comes running after them, and scares Pikachu's new friends away. (We are 36 episodes in at this point, so I don't know what part of "Wild Pokémon behave differently," Ash doesn't understand.) Naturally, Pikachu is heartbroken, but he quickly reunites with the group after saving one of them from going over the edge of a waterfall.

Later that night, Ash, Brock, and Misty watch all the Pikachu perform an adorable little song-and-dance routine under a full moon (I guess Clefairy aren't the only Pokémon fond of moon-worship). Then Brock opens his mouth and utters the dumbest sentence ever: "I think it's the best thing in the world for Pikachu to be here with its own kind."

Brock's just saying it's a good thing that Pikachu has made some wild buddies. But Ash, in his infinite 10-year-old wisdom, takes it literally. His experience with letting Butterfree go may come into play here; it seems the lesson he learned from that whole ordeal was, "If you love something, let it go." Ash stays up all night pondering this, but his train of thought is broken when he hears Pikachu and his wild new friends calling for help.

Team Rocket has apparently improved their Pokémon-catching technology, trapping all the Pikachu in yet another giant net (though this one is resistant to electricity). Thankfully, the net isn't teeth-proof, and with help from the same wild Pikachu he saved from the waterfall, Ash's Pikachu bites a hole in the net, allowing everyone to escape.

Once safely out of Team Rocket's clutches, Pikachu gives Ash a big hug, then goes over to check on the smaller wild Pikachu who helped chew through the net. They engage in an adorable victory chant, and Ash, for some reason, takes this as a sign that he needs to abandon his beloved Pokémon, White Fang-style.

"All of the Pikachu here in the forest need you," Ash tells him, tween angst turned up to 11. "So just… GOODBYE!"

Pikachu is understandably pretty torn up about this whole thing, and tries to follow Ash, who yells at him and darts off into the forest. We're then treated to another flashback montage, but because Pikachu has always been an adorable little thing, the scene is genuinely heartbreaking rather than accidentally hilarious like the Butterfree flashback. (There are some pretty funny shots of Ash getting accidentally electrocuted, though.)

Another reason this scene works so well is because Ash and Pikachu have been buddies far longer than Ash and Butterfree. Ash is basically abandoning his beloved childhood pet, and it's all self-inflicted. Butterfree wanted to fly off with its mate. While Pikachu's obviously happy to have made some new friends, he never indicates that he wants to ditch Ash for them.

Thankfully, Brock and Misty catch up with Ash and tell him what a dumb-Ash he's being. Pikachu arrives soon after, bids his horde of wild buddies goodbye, and tackles Ash, making it clear that he wants to continue their adventures together. While this episode ends on a happier note than "Bye-Bye Butterfree," I've always found it to be a much sadder episode, in part because of how close Ash and Pikachu are, and in part because the entire ordeal is a result of Ash's failure to communicate. Ultimately, Ash hurts himself — and his favorite Pokémon — in his confusion. Butterfree's episode is about doing what's right for a Pokémon, but Pikachu's episode is basically about abandoning your pet in the woods because you're an insecure idiot.