Pokémon Gold and Silver: Whitney

Everyone knew this was coming. Whitney remains nightmare fuel for anyone who played the original Gold and Silver on the Game Boy Color. Her Miltank is an icon because she literally rolls over every poor, innocent Pokémon who is unfortunate enough to face her. Whitney acts as a tutorial for a mechanic the player is likely not privy to when they show up at her gym in Goldenrod City. She knows Rollout, a rock-type move that doubles in strength with each successful use. It’s disorienting in a few ways. It’s a normal-type gym, but the most powerful move Whitney has at her disposal is a rock-type move, so you might not be prepared for this since you came ready to fight normal-type Pokémon. It’s also unclear that Rollout gets stronger with each use, so you don’t know why each Pokémon Miltank knocks out seems to be taking more damage than the last. But that’s her whole strategy. Whitney steamrolls your party with a constant barrage of increasingly powerful attacks. The only way to stop the multiplier is to either knock Miltank out or interrupt her streak, whether that be through defensive abilities like Protect or, by some miracle, avoiding the attack entirely.

This is the third gym battle in Gold and Silver, and it became a staple in conversations around the series’ most challenging battles. If you know the strategy, it’s easier to counter, but for most of us, Rollout was this new, unknowable thing we had to trial-and-error our way through until the cow Pokémon was knocked on its ass.