Whitney – Pokémon Gold and Silver
In retrospect, Whitney isn’t that tough of a fight if you’re well-versed in the mechanics of Pokémon. But most of us weren’t that smart when we played Gold and Silver because we were kids 23 years ago. Her Miltank remains a core memory for Pokémon fans because she taught us all a lesson on the importance of status effects and stopping your opponent from just attacking without interruption. If you don’t move to stop it, her Miltank will just spam Rollout on your entire team, its blows doubling in strength with each successive attack. The fight is also made difficult by the dearth of fighting-type Pokémon in Gold and Silver by this early point in the game, so the usual strategy of just exploiting Miltank’s weaknesses is its own challenge. Tears of frustration ensued, and the fight became an early catalyst of gamer rage for many a young child. — Kenneth Shepard
