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Pokémon Season 1 Episode 45

Entering Neon Town, a bustling Metropolis where everyone is tired and rude, Ash and his friends find a Jigglypuff who is too shy to sing its hypnotic song. Realizing they can kill two birds with one stone, Misty tries to teach the Jigglypuff to sing while Team Rocket attempts to record the song so they can use it against Ash. Everyone falls asleep, including Ash and his friends and Team Rocket, and a miffed Jigglypuff uses the marker hidden in her microphone to draw on everyone’s sleeping faces. From this point on, Jigglypuff follows Ash around trying to sing her song to a crowd that will not fall asleep in almost every episode.