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Cyndaquil. I always loved his design, he's so cute! I also picked him as my starter because of Gold from the manga, one of my favorite characters. Also, Typhlosion totally rocks.
I chose Totodile because i really like Crocodiles/Alligators and thought his design was really cool.
And back in the day i still watched the Anime, and i loved how Totodile would bite everyone :D
Not sure why, but my first time playing silver I picked Chikorita...I can safely say that's a mistake I'll never make again. I f I were to play nowadays, I'd go with Cyndaquil.
I picked Chikorita as my first choice. I also did new games with Shiny SCyndaquil, and another save file with Totodile since i ucould use a vulpix with a fire stong.e
I chose Chikorita because I wanted a challenge.
In the beginning of Silver Geodude and Zubat are avalable and they complimented Chikorita nicely.(i think my sign. has my trainer card from johto)