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Who do you think was Ash's best traveling companion in the anime? I would say Brock as he was with Ash more than any of his other companions, and has helped him out the most too.
If it's just based on how helpful they've been and how they've affected Ash/Satoshi's growth... For me It's got'to be Brock/Takeshi. Great cook and a friend willing to follow you through hell and back.
I went with Brock because he was with him the longest and he was like Ash's older brother, helping him and the other companions and being very knowledgeable about different types of Pokemon. I do feel the hate Tracey gets is undeserved and he was underrated. He was very helpful and knew a lot also, maybe even more than Brock at times, and didn't get distracted by women like Brock. I wish he traveled with Ash and Misty a little more, although I think having him with the two of them plus Brock through Johto would've been too much.
I actually think it's Dawn. Not just because she and he are really really close either, though that helps a ton. It's because Dawn was with Ash the most she could be. Even despite her own goals and dreams, she somehow made journeying with Ash her thing. Other party members came and went with regularity in Sinnoh; but Dawn rarely ever split up and took a different path than Ash did; and only when necessary.
Granted that alone, Dawn probably would have been in lots of trouble; despite her brilliance as a coordinator; she really wasn't all that great at battling much until Ash got to know her and taught her a few things.
While Brock has always "Just been there" for Ash as much as he could; he's kind of like an older brother. Yes he contributes to Ash's growth; but not directly, ever, the way Dawn does by being Ash's 'student' in plenty of ways. Brock is good at making sure Ash isn't lacking in survival skills. But that's all Brock does. He never really spends a whole lot of time teaching Ash how to be a better trainer; instead he seems to expect Ash to figure it out. I suspect that's just the Gym Leader streak in him. Brock always seems like he'd rather just be there to impartially officiate Ash's Battles than to do much else. Of course he also spends a lot of time chasing skirts, the dirty boy. It seems to fall on the "Female Companion" of the generation or moment to give Brock the "Down Boy!" treatment. I can't fault Brock for his Loyalty to Ash but I also know his motives aren't just for Ash nearly as much as they are for himself. Ash endears himself to many, many ladies. Brock enjoys this. A little too much sometimes. ;)
Brock was the most dependable member of Ash's companions. He brought a little wisdom, a little comedy and little comfort in my eyes. Sure he didn't have as much to do as some other members, but as someone who I'd like to see stand by Ash's side most(Not counting Ash's pokemon, though), it'd be Brock.
Misty. I love her fiery personality but she always had a softness to her. I love that she was specifically a water pokemon trainer too and it's a shame we couldn't see more of her working towards her goal and I hate the way they just abruptly ended her storyline and haven't bothered to show her again in, what is it... 10 years now?
I also loved the little running gag they had with her always dragging Brock away from the women he always flirted with so by that extension I do really like Brock as a companion as he was always reliable and I don't think Ash would have survived most adventures without him.
I do have to give a shout out to May as well though, I wasn't really a fan of her at first but when she found her own goal she wanted to work towards I began to really enjoy watching her character and I wish we could have seen her win a Grand Festival :(
I voted Dawn out of my love for the DP series having grown up with it.
But thinking about it more, Bonnie is by far the best character.
She's adorable, can hold episodes by herself and more importantly:
Spoiler:
It's because of her that Punichan stops destroying the city/Z2 seeing the value in humans and stopping Lysandre. She is essential to the plot - without her the whole world dies.
Since when did a character who is supposed to be background/comic relief become so important? Arguably she's more important than Ash in that regard!
Dawn: I think she was one of Ash's most goal oriented companions. There were plenty of episodes dedicated to her catching and training her team. Her contest battles were so creative. She also would cheer hard for Ash in both the Sinnoh aaaaaand M8 tournament- being Ash's only friend to fly out to surprise him
Of the Anime gens I've completed so far (1-3&6-7), Brock is the most consistent. While some people might call it blandness, I don't think there's anything wrong with a character being written consistently, particularly as a supporting character.
To me it's impossible to choose. Too many of them fill entirely different roles and are equally good at those! Brock is a rounded, fun guy who's just around most of the time. Serena is a passionate girl trying to figure herself out. Iris is fighting to become the best at what she does, training dragons... I could go on. Can't pick one :')