Kanto- When I was a wee lad, I loved the Charizard line like many others... but now, I find all three just really badly designed. None of them fit my style of play and they all just look fat and ugly >.> If I had to pick, then Bulbasaur. Cause Bulbasaur was bloody adorable.
Johto- Cyndaquil. This thing is cute as all hell. the squinty eyes, the little snout..... it made me fall in love with this Pokemon. Oh, and did I mention that ITS SOOO CUTEEEEEE. Quilava had a nice sleek design too, with its smooth body and flames. Pity that Typhlosion looked bad....
Hoenn- This is when I started to pick the Pokemon that fit my style - namely fast offensive ones. Treeko is my choice, cause Torchic too mainstream, ya? Plus I love Grovyle and Sceptile's designs. It looks so badass, and the anime must be crazy to not give Ash Mega Sceptile. But hey, Charizard MVP amirite?
Sinnoh- Fave Generation, with probably all starters in my Top 5 favorite ones ever. Empoleon looks badass as hell, and Torterra is terrifying when you face it (it has a bloody ECOSYSTEM on it's back), but the clear winner is Infernape. This monkey was so cool, with the flames on it's head to it's regal markings on it's body.... paired with some powerful ass moves.... What's not to love?
Unova- Second fave Gen, and Tepig was adorable (while Oshawott was not) and Pignite and Emboar looked terrible (while Samurott looked badass). But Snivy- It goes from Cute to cool to regal in a couple evolutions and it's just so much better looking than the others. Not to mention based Contrary. >.>
Kalos- From looks, I'd pick Fennekin. BUT Delphox is just so..... ugh. Disliked Chispin's entire line, including grass Pignite and the Hunchback of Kalos. Froakie is too mainstream though, but I'll just say that it fits my style to make me seem more original :3