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Chimchar, because I started out with Piplup the first time round, and didn't really like Empoleon's move set, and I don't like Grass type Pokemon (although they are handy in some instances) :D
I chose Piplup. Normally I choose fire starters, with the only exception being Treecko in R/S/E. But I absolutely adore penguins, and Piplup was just too darn cute to pass up. Plus, I love Empoleon's excellent defenses afforded by his Steel type. I would usually switch him in as a wall after weakening a legendary so I can just chuck Ultra Balls over and over without worrying about my Pokemon taking too much damage.
Pearl (first played) - I chose Chimchar cuz I like Fire type and its fast and a good ATK and Sp.Atk stat.
Diamond - Piplup is here cuz i've played the female character just like to match the anime.
Platinum - Turtwig cuz it's the only one left to try and absolutely like it for being to learn EQ and solid ATK stat.