Characters I Strongly Like (Bold Indicates Characters I Absolutely Love):
OS Ash and AG Ash- OS Ash has a lot of hidden depth to his character and I like him the most out of all Ash incarnations if only for the fact that he actually acts the most like a real 10 year old boy would, and that is at his core who Ash Ketchum really is, but it's not just that: this incarnation of the character was also the most realistic, acting more like a real human being than others would- he would get angry, he would get sad, he would get mad, he would get happy, he would get livid, he would act mature at times, act immature at other time, and he was generally capable of showing a great variety of emotions that is not found in any of his successors excluding AG Ash. What strikes me as the most amazing thing about the character, though, is how selfless and honorable he was: he was willing to let himself DIE to save the people and Pokemon he loved, he would do anything it took to protect what he cared about, and he would always have the courage to stand up even after suffering defeat and get even stronger from it. Additionally, this was only complemented and made even better by Veronica Taylor, whose voice perfectly complemented Ash in being both age appropriate for a 10 year old boy, as well as her acting being full of life, energy, and enthusiasm, with a genuine laugh and genuine crying that made you sympathize and relate to the character's strife and internal struggles.
AG Ash has a very humble and down-to-Earth personality that I found was very easy to identify with, and he had many of the characteristics of his predecessor, while also being a little more calm and rational in his thinking when it came to battling, strike a great medium between being a good character and a good trainer, but wasn't as selfless or honorable as his predecessor (though still quite a bit in the first few episodes of AG and in the Lucario Movie), but was still a very good and like-able character to me (see OS Ash description for Veronica Taylor's voice complementing this incarnation of Ash as well-- it applies here too).
OS Brock and AG Brock- OS Brock was easily the best incarnation of the character and he was the wise, smart, calm, collected, and yet extremely funny mentor to both Ash and Misty, the guide for when they would get lost, as well as the more mature and level headed member of the Original Trio. Brock in this saga demonstrated profound depth to his characterization in terms of, much like OS Ash, being very self-sacrificing and selfless in caring for Pokemon by staying up all night to take care of them, to be willing to let himself get run over and mauled to help others, and also had a flirting gag that was not overplayed or abused too much that was, at this time, actually genuinely hilarious. He also developed a lot as a character as the saga progressed, and Eric Stuart's voice perfectly complemented him to a tee, being age appropriate for a 15 year old teenager, while also managing to strike the serious and comedic chords of the character with ease and making him feel like a wise older brother to the group.
AG Brock is the same as OS Brock, but his flirting gag was run into the ground a little bit more and he didn't get quite as much screen time as his predecessor did, but fortunately Max was there to keep him company and helped keep Brock more like-able in this saga, and what I said about Eric Stuart's voice for him above is, once again, directly applied here. In addition, I found Brock was at his peak in terms of his Pokemon team and as a battler in this Arc, having Pokemon in his arsenal as strong as Marshtomp, Ludicolo, and ones at the Pewter Gym like Crobat and even a Steelix that kept him company.
Misty- She developed a lot over the course of the Series, and I always enjoyed her tomboyish and snarky ways with Ash and at times, Brock, but was also genuinely kind and sweet underneath that tough appearance she made for herself. She was very interesting to watch grow over the course of the Series, and is without a doubt my favorite heroine on this Series- I also like how as time passed, she began to mellow out and her Pokemon team actually got a lot stronger with the addition of a Politoed to her arsenal. Rachael Lillis' voice complemented her perfectly, but that's implied, of course.
Max- I think he's possibly the most underrated character on the show and while he could get a bit annoying with the snarky comments at times, there was a lot more to him than his stereotypical nerdy appearance would have suggested, and the sixth Pokemon film and episodes like "Do I Hear a Ralts" as well as the episode where he befriends Deoxys show this to be true. Additionally, Amy Birnbaum's voice for him fit him perfectly and she made him sound just like a real 8 year old boy would.
OS Team Rocket and BW Team Rocket- What can I say about OS TR? They were genuinely funny, intelligent, like-able, and actually had individual personalities with very intriguing backstories, James coming from a rich family that refused to accept his lower-than-upper class behavior or desire to be free from the clutches of his fiancee Jessibelle, Jessie coming from a downtrodden family struggling to make ends meet, and Meowth learning to talk in an attempt to impress the Meowth he loved, but then being coldly rejected and called a freak just for talking like humans would. Additionally, Eric Stuart was a perfect fit for James making him sound suave, debonair, and yet also hilarious at the same time, Maddie Blaustein was able to handle the harsh exterior of the character very well while also nailing the softer, gentler side of Meowth, and Rachael Lillis was a perfect fit for Jessie making her sound like the diva and tough woman she really is.
BW TR, however, I liked for how far they were progressing towards their goal and how they had finally obtained Giovanni's respect as well as having an air of seriousness and competence to their actions that had barely been seen before, while also being quite interesting in the ways they managed to do things other than stalking Ash continuously for his Pikachu.
Iris- Most dislike this character, but I am definitely not one of them: I love how she criticized Ash for acting like an idiot when he was, I like how much she grew over the BW Series and became confident in her own abilities as a trainer worthy of raising her Excadrill and other Pokemon, as well as her showing a lot of kindness towards her friends under the facade of being tough and hard on the outside.
Cilan- A complete breath of fresh air for the Series after the very stale DP Brock took his leave, and his enthusiasm was downright charming for things, and he was just hilarious but also quite interesting to see interact with his brother Chili and he was like another brother to Ash.
Characters I Somewhat Like:
May- She grew a lot over the course of the Series from a girl who was unsure if she liked Pokemon at all and even wanted to be involved with them at all, to a girl who became fully confident in her abilities as a Coordinator and showed profound growth in both that and her character as time progressed. Veronica Taylor's voice for her was perfect and sounded just like a 10 year old girl would, but she also put a lot of energy and charm into her voice that just fit her so well, too.
Dawn
AG Team Rocket
BW Ash