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ex) Kecleon has been a favorite of mine ever since I first saw him. His design is delightfully simple and efficient, but all-around great, and he's just such a unique pokemon that I find it hard to pass him up. I love his concept, character, and design. It works less often than I'd like, but setting up a Skill Swap on something is always hilarious, especially when I start wailing on them with Shadow Claw/Drain Punch/Knock Off for that recursive super-effectiveness, support, and recovery.
ex) Just like Kecleon, Sableye became a mainstay in my favorites since I ran into it in Granite Cave. His stats may not have been the best and he generally had little going for him competitively (this is third generation, mind you) but I stuck with him out of sheer admiration. A gem-faced shadow imp with no weaknesses? How could I not love it? The expanded movepool in Gen 4 and Prankster in Gen 5 were godsends, and while I'm overjoyed at his newfound viability, I take a bit of smugness in knowing I liked him before it was cool.
ex) Armaldo. I picked up the claw fossil out of pure chance and it turned into an Armaldo. I thought it was adorable. Then, all of a sudden, BAM, it evolves into prehistoric Godzilla! Fell in love immediately. After digging another Claw Fossil out of the Sinnoh Underground and breeding it some, Ivan the Armaldo became my first ever pokemon to be raised for competitive play. Recently I've raised another, Alexander, who is based more in defense and support than raw offense, like Ivan.
ex) Slowbro and Octillery I both love, but I couldn't choose. Slowbro, however, had an absolutely hilarious picture, so he got the spotlight for the square.