Keaton was the first one for me. I remember it because I initially thought he was really weird. Telling me I look cooler than a fair number of cucumbers and all that. That was before I knew about the smug personality type. I ended up liking his weirdness after a while though.
Beardo was my first smug, he moved in just a few days after I started my town. He became my favorite smug, but he moved away accidentally.... Now I have his Amiibo card so I can move him back in!
Hans the Gorilla, He still haunts my dreams ;_;
I tried to like him at first, but that creepy face stares into your soul. and this one time when I refused to let him over my house he said "ok, I'll just wait her while you figure out your feelings for me", Like omfg I was so scared!!! not even marshal has ever said that too me!! plus he started wearing Cally's shirt, LIKE HOW DOES THAT FIT HIM ITS SO CREEPY HE LOOKS LIKE HES TRYING TO BE CUTE!? whats more his house was just above mine so I felt like my privacy was.. violated... I then proceeded to shove him into pitfalls and hitting him with a net. you could imagine my happiness when he said he was moving... I was so obsessed when I first saw marshal, of course he had the same personality but somehow he never said the same things Han's did? Marshal is beyond my preference when it comes to smugs.
I'm not the only one who finds him creepy... http://www.gamefaqs.com/boards/997811-animal-crossing-new-leaf/66602099
Eh, I think Graham was my first. I don't ever recall him changing his shirt so I don't think I interacted with him much before he moved out. In fact I don't remember him being around for very long either. Creepy little hamster. I prefer my dear, sweet Lionel. <3