Charmeleon

This is the second stage in the evolution of Charmander. When Charmeleon swings its burning tail, it raises the temperature around itself to unbearably high levels.
In "Showdown at Dark City," Ash's Charmander evolves into Charmeleon in an adventure in the decimated city known only as "Dark." Here our heroes get caught up randomly battling the local gym trainers throughout the town, destroying things wherever they go.

First appearance: Episode 42—"Showdown at Dark City"