Chimchar for me. It always served its role pretty well, and I do like monkeys!
I've only played through Sinnoh once, but I picked chimchar. :3 My little brother wanted piplup, so it was between turtwig and chimchar (I didn't know any of their final evolutions. I was jealous of empoleon when I learned it was part steel).
The Gen IV starters were all so fun. I mean, it was between a monkey, a penguin, and a turtle, and those were all really "cool" animals at that time. xD
In Diamond, I chose Chimchar as my starter.
In Platinum, I chose Turtwig. o3o
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Chimchar, I always liked the little monkey.
Piplup and then when I replayed it was turtwig, never picked chimchar before though
I have claimed Skarmory
Turtwig loved torterra i Soft resetted for a shiny one and MM'd one in B2
I chose Turtwig first. Not a monkey fan, and not exactly a penguin fan either, so I chose the turtle xD
Turtwig, I had a pet turtle at the time. Besides, I thought Chimchar was butt-ugly (knew nothing of its eventual battling prowess) and Piplup had weird white nipples or something.