In order:
1. James: Ah, James. How I love him.
For starters, he is by far the most humorous character from the series. In practically every episode I have seen, he has managed to get me to laugh. He is such a funny guy.
Despite being a villain, he is actually a nice person. He may think he is evil, but he is truly a softie. He has a kind nature not seen in most people. He is very gentle and sensitive, not to mention loyal.
Sure, there are times in which he can be whinny and break down emotionally, but he is also capable of being brave and heroic. He is actually a dependable guy who would sacrifice himself for anyone he cared for.
Contrary to popular belief, he is not dumb, far from it. He is naive, but naiveté is not the same as idiocy. In actuality, he is intelligent and holds a lot of knowledge.
Knowing what his childhood was like, it is impossible not to feel empathy for him. Even though he came from a wealthy background, he had a harsh upbringing. I hate his parents for all the suffering they subjected him, from making him take numerous painstaking lessons to betrothing him to a cruel sadist.
Furthermore, he is by far the hottest man I have ever seen, anime or otherwise. He also has a sexy voice in the 4Kids dub from episode fifteen onwards.
If James was real, I would be all over him. He is fine<3
2. Jessie: Jessie may act like a ***** most of the time, but she does in fact have a good heart. Having lived a difficult life and experiencing numerous let-downs are probably what caused her to develop a harsh exterior. However, beneath it all, she is a kind and caring person.
Furthermore, she is strong willed, independent, and determined. I also like her relationship with James. They share excellent chemistry and their personalities balance out with one another perfectly.
3. Meowth: I like Meowth's wise cracks. They are funny. Being the brains behind the TRio, he is of course very intelligent. I also admire him for all the effort he put into learning how to walk and talk. Shame that Meowzie rejected him anyway. Now he is a chaser for Giovanni XD
4. Gary: Gary has undergone excellent character development over the course of the series. He started off as a condescending jerk, but gradually became a kinder and more mature young man as the series progressed. Overall, I would say he is a dynamic and well written character.
5. May: She is an airhead, but a friendly and cheerful person. She also underwent outstanding character development during her run on the show. At first, she was a joke who did not like Pokemon, but gradually became a great co-ordinator who loved Pokemon over time.
6. Brock: Brock is an interesting character. According to PokeAni, the reason he skirt chases is because he longs for a mother figure in his life, which he never had growing up. Sadly, he became stale as the series continued. If I was writing the show, I would have him find a girlfriend and leave.