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Top 65 Pokémon Boys:
Disclaimer: There can potentially be spoilers in this description. Read at your own peril.
65: Egan
An amusing hot-headed fire type trainer from the episode "Some Like it Hot". Had some amusing back and forth banter with Misty.
64: Pete Pebbleman
Ash's third opponent in the Indigo Pokemon League. Appears in the episode "Fire and Ice". He has an Arcanine which propelled him on here and a had a pretty good strategy. Just wish we could've watched the full match between him and Ash.
63: Mantle
He’s from the XY episode “Rotom’s wish”, it was a pretty good one if you want to check it out. I liked how he battles with a Krookodile and takes over a hotel and battles trainers for their Pokémon. An interesting one shot villain, I thought I’d have him low on the list, but I certainly remember him enough to get on this list.
62: Shingo
A trainer who loved battling with a laptop sounds like my kind of trainer. 
One of my favorite episodes from season 3, "Wired For Battle". Later gets a lesson from Ash after being defeated by his Heracross.
61: Drake
We all know him from being the guy Ash beat at the end of the Orange Islands. A tough trainer that gave Ash a great battle. Can't soon forget him and the battle with Dragonite.
60: Paul
"Talk about pathetic." Yeah, sure he's quite a base-breaker, but some of his jerkass character can be quite amusing, plus he does bring in some refreshing conflict between Ash and the group. If only he could've had a bit more of a pay for his actions, but him losing is probably bad enough for him.
59: Cheren
I feel he’d be a realistic trainer if we were all in the Pokémon world, seeking out the strength in Pokémon. Like I said with Bianca on the girls meme, he has a nice contrast with her and instead picks the advantage Pokémon over you, making him a more difficult rival. Some of his lines were funny.
58: Kabu
The new fire type gym leader in Pokemon Sword and Shield. While I don't think he's as memorably as Blaine, I did like his design and it's fun seeing more fire type gyms, so I added him on to this update.
57: Blaine
His riddle filled episode was pretty funny, with Ash always guessing wrong. Such as Ash thinking to what is hot and cool at the same time was sleeping in front of a fridge while wrapped in an electric blanket. He also had a Magmar, one of my favorite fire type Pokémon, along with one of the best Kanto gym battles in the show.
56 : Colress
Internet Explorer hair! Was totally a surprise to see him again in Sun + Moon. Not as much of a villain as the rest of his Team Plasma colleagues were and thankfully he denounces them at the end of the game. A shame that the anime made him more villainous but still wasn’t as bad as Ghetsis.
55: Lysandre
I was always amused how tall he is. Also I love his lion motif with his face. I wasn’t a huge fan of Team Flare in the game, but Lysandre was fun to have around.
54: Hau
I wasn’t sure at first how I was going to react with Hau, being another friendly rival, but he managed to be fun, keeping a positive attitude throughout. There was one scene I liked where he told a joke and you can choose to not get that it was a joke resulting in a blank stare. Also, he has a Vaporeon if you choose Litten for your team. Thankfully before every battle he also heals your Pokémon.
53: Tierno
He had an interesting personality, acquiring dance moves into his battling. I wish he had a little bit more with him, he didn’t appear all that much in the game or the anime, and when he was around you mostly just quickly battled him and that was it. He wasn’t too challenging either. Still, a big goof like him deserves a spot on the list.
52: Sawyer
He was a Hoenn rival for Ash in the Kalos region, so I felt I had to include him here. He had the Treecko line, so that definitely adds points to him. Again with the anime though, a huge missed opportunity to bring up Ash’s Sceptile. Anyway, it felt really good seeing him improve and even beat Ash in a battle, and he put up a great fight in the semi-finals.
51: AndreasCharacter of the day from the episode "Hook, Line, and Stinker". Like Egan, he had a lot of amusing moments with Misty that was just so amusing how such childish banter got under Misty's skin. Like, Shingo he was humbled out after being defeated.
50: Jirachi
My favorite Pokémon movie was perhaps Jirachi’s Wishmaker. I loved Jirachi and his friendship with Max. One of my favorite moments was when May demanded he get rid of the problem and Jirachi teleported her away and said “problem gone”.
49: Latios
As Latias was on the girls list, add Latios to the boys list. Love this blue dragon Pokémon and acquiring him in Omega Ruby. He definitely came in handy against other dragon types.
48: Maxie
Of course I had to add the leader of Team Magma. He seems as calm and collective as Archie on the outside, but just as insane on the inside. I loved when I played Sapphire as a kid, you had a bit of time playing as an ally to Team Magma.
47: Kiawe
Alola Marowak is my favorite Alola style Pokémon. His trial is also pretty amusing, with the pictures and him getting confused how we could possibly get them right. I wish the trial captains did a little bit more. He’s been pretty awesome so far in the anime too.
46: Wally
Sure was a pleasure seeing how much he grown from the beginning of the game to the end, becoming a more efficient rival. While I still might prefer the relationship between Brendan/May, he was still fun to be around. He had an awesome Gardevoir and insists he won’t give up becoming a powerful trainer. Got to love his determination.
45: Hop
Meet your new friendly rival from the Sword and Shield games! Yeah, Hop was nice and helpful and he does go through quite the bit of development throughout the game. Starts off ambitious, then insecure to confident again and then decides to take a new path. He's a great friend to have in the game and earns a spot on this list.
44: Jessie's Wobbuffet
“Wobbuffet!” Need I say more? Definitely brings funny moments and charm to the anime.
43: Butler
Rather than being a villain looking to take over the world for their own need, Butler was a villain trying to prove Team Magma wrong by bringing back Groudon. He was a character with background and I appreciated that in Jirachi’s Wishmaker what makes it one of my favorite Pokémon movies. I love he reforms at the end because of his love for Diane.
42: Timmy Grimm
I loved his Dusclops costume and how he battled under a persona, I thought it was cool and unique and loved that he kept it on during his contest against May. He even managed to beat Drew and knocked him out from even entering. Was a shame he didn’t show up at the Grand Festival.
41: Trip
His character definitely improved throughout the Black and White series, it’s a shame his first impression wasn’t good, seeming like a Paul ripoff and the infamous Pikachu losing to a new Snivy. It’s as much of a shame is when he did develop into a better character the writers basically dropped him for other recurring characters. Still, I liked what he progressed into and I loved seeing his scenes with Alder, and that he was able to win the Junior Cup. A shame he didn’t go further in the Unova League. One of my favorite moments was when he showed Oshawott’s problem to Ash.
40: Nate
I've enjoyed coming up with some headcanons for Gen V characters and Nate was no exception. Would probably be higher if I personally experienced Gen V games myself, particular B2W2, but he's still been fun to play around with. Also amusing that he shares the name of the main character from Yo-Kai Watch.
39: Gladion
He sure is amusing. I love the facial expressions he makes throughout the game, like when he loses. I also like when, along with Hau go into the Aether Foundation he teams up with you and you battle the Aether people. All to save his sister Lillie, so it shows he’s got heart, as he shows with Type: Null. Definitely like how he gives you one in post-game.
38: Harrison
One of the best battles of the series, he sure gave Ash a run for his money, and ultimately won in the end thanks to Blaziken and a tired Charizard. Was certainly an epic moment in the series. As such, he introduced Hoenn to the anime, and as Hoenn is my favorite region, he’s got to be on the list.
37: Tyson
An epic character like Harrison, what puts Tyson with an edge is he beat Ash…with a Meowth! A Meowth in boots, an obvious parody of Puss-in-boots, another awesome character. That and the fact he won the whole Hoenn League, the first rival of the series to do so.
36: Giovanni
I may like Team Magma more, but Giovanni is the best boss. He’s a simple mafia-like boss, but it’s that simplicity that I think makes him the best. Just bring him strong Pokémon. No desire to destroy the world, just steal trainer’s Pokémon. I also loved his voice in the early seasons of Pokémon, he was much more intimidating than he is now.
35: Ash's Infernape
The poor suffering he took from Paul at the beginning as a Chimchar, which he was very cute by the way. Thankfully Ash trained him properly to his potential and became quite the badass Infernape!
34: Professor Birch
The Hoenn professor, so, of course. It was funny seeing him get attacked by various (weak) Pokémon and needing you to save him.
33: Professor Oak
The original professor, so of course he would crack this list. I remember he was a lot more snarky in the first episode. He actually had Ash open all three empty Pokeballs when he knew they were already gone. Also, the time when Ash called him when he caught a Krabby and he’s eating crab and then showed Gary’s much more enormous Krabby. Still, it was clear he supported Ash throughout and cheered for him after Gary was eliminated.
32: Ash’s Oshawott
His show-off personality was more amusing than annoying to me. Also he had his adorable moments too, saying “Osha”. I remember the small arc where he was afraid of opening his eyes in the water, as said in the Trip selection. Also loved his cute rivalry with Tepig/Pignite. I wish he evolved into Dewott, he could’ve stayed cute and be even more badass at the same time. Oh well, hope for the future.
31: Cilan
“It’s evaluation time!” I think he was a good replacement for Brock and shake things up moving on. His evaluations on Pokémon were certainly something unique, so at least he wasn’t a clone. He had a neat Pansage too.
30: Trevor
Weird haircut, right? Still, he was a nice good guy character. Like with Tierno, it would’ve been nice if his character was explored a little more other than just wishing to fill up the Pokédex. In the anime he took up Pokémon photography and I loved how excited he gets when showing off his pictures. Definitely deserved better in the Kalos League. Another thing that was fun to watch, his Charmander/Charmeleon having quite a nice contrast, as he wanted to fight all the time with Trevor being so nice and all.
29: Clemont
I have Clemont over Cilan in that I thought XY was a better series. He also had an amusing catchphrase (“The future is now thanks to science”). I always loved how he would gleefully explain his inventions and then they would always blow up in his face. Bonus points if everyone points out that they know what’s coming in a matter of moments. Another funny thing is how flustered he’d get whenever Bonnie tried to hook him up with another girl. As of writing, the XY series is now done. So long, Clemont, it’s been fun while it lasted.
28: Victor
I do like the new boy trainer from Pokemon Sword and Shield. His design feels like a bit of a mix of Brendan and Hilbert, and they're two of my favorites as you see, so this definitely is a nice pick. As I said in the girls rankings, I like the contrast with him and Gloria.
27: Allister
My favorite male character from Galar, and ironically I bought Sword. Still, watching Shield gameplay, I know I have him on here thanks to his design, personality and fan art. Hope to see him in the show soon.
26: Ash’s Totodile
I miss Totodile, he was cute dancing around. Would’ve been cool to see Ash with a Feraligatr, my personal favorite of the Johto starters. I always looked forward to seeing him in the Johto episodes and he certainly held his own in battle.
25: Ash’s Squirtle
The unforgettable Squirtle Squad. Got to love his sunglasses and mischievous nature. He’s another Pokémon I’m quite surprised didn’t evolve, but I guess that’s why they’re the Squirtle Squad. XD
24: Ash’s Hawlucha
My favorite Pokémon Ash had during the XY series. I loved how he loved to show off his moves, and who could forget his awesome costume during the Kalos League? I loved he had his chance to shine for real in the Valerie gym battle and how he acted as a big brother to Noibat was adorable.
23: Tate
Same as Liza in the girls list, I can’t believe how long I held off on him on this list. Along with his twin Liza, they’re the only double-battle in a gym through the whole series. That definitely makes them stand out, and everyone loves twins so he has to be on here. As for his anime counterpart, I thought he was great there too. I love how he got easily annoyed with Liza teasing him and how he related to Max on how annoying older sisters can be.
22: Brawly
I loved his laid back personality and calm demeanor, especially for a fighting type gym leader. When Ash came in to challenge him thinking it was going to be easy it was a pleasure watching Brawly hand his ass to him and humble him out of his winning streak and set him on a better path for the rest of the Advanced generation. Way to go Brawly!
21: Norman
Coming from a lifelong monkey lover, he’s got the best evolution line for a gym leader in the whole series. I especially loved his Vigoroth in the anime series, and how he twice knocked out Pikachu, though the second one was a draw, it still counts. Another moment I love of him is when he set up fireworks for his anniversary with his wife I thought was real sweet. Also, as I said with Caroline on the other list, I love that generation three had us with both parents and that when you earn the badge it says you won from your dad instead of gym leader.
20: Calem
It was fun playing as him in Pokemon Y. So, as much time as I've spent playing in Kalos, I've had to add him. Also the fact that a lot of the group shots I've seen with him and the other characters of Gen VI were pretty cool. 
19: Brock
Some people might get annoyed with his constant flirts with girls but I always found them funny just cause of how over the top his lines were. I loved when he explained the differences between the Officer Jennys during the Pokémon League, and him getting dragged away by either Misty or Max was funny too but the cake had to be getting a poison jabbed and then dragged away by Croagunk in the Diamond and Pearl series. Hopefully offscreen he’s becoming a successful Pokémon Doctor.
18: James
You got to appreciate how kind he always was to his Pokémon. For instance, the fact he caught Cacnea with a bag of cookies and Cacnea thought he wanted them returned and then he caught it. Also the running gag of being attacked by his own Pokémon like Victreebel, and of course Cacnea hugging him as he’s a cactus and Chimecho blinding him. Why does he always get adorable Pokémon? How he befriended Cacnea solidified him on the list for me but I always loved Team Rocket so he would’ve been here anyway, that just moved him up in the top 15 for me. Oh yeah and I thought it was cute he called Growlith “Growly”.
17: Drew
He’s got an awesome chuckle that always amuses me. He was a great rival for May, he never crosses any line and even once warned her about getting overconfident, so he wasn’t just a huge smug ass. I may be a Hoennshipper first, but I especially liked Contestshipping in the anime, and I hope he can win a Grand Festival in the future. Sure, it might be offscreen, but it can still happen.
16: Max
I understand some flaws that people point out about this character, but I don’t care what the haters say. Of all the characters Ash traveled with, Max had the best introduction by far. Rubbing in Ash’s failure at the Silver Conference (“but you still lost right?”) makes me laugh every time. A lot of haters point to the scene when he stole Ash’s balance badge as a reason they hate him but I actually found that moment to be one the truest scenes in the anime. They forget to leave out all the time that Max came around and presented Ash the badge afterwards, but it was completely understandable it was hard for him to see his dad (the most powerful trainer he knew) lose. Give him a break. I also mentioned before how Jirachi’s Wishmaker is one of my favorite Pokémon movies, and I liked his relationship with Jirachi. Another awesome episode from the series was “Do I hear a Ralts” which is not just one of the best episodes of Advanced, but one of the best episodes of the whole series that I actually ranked it as my favorite in the controversy meme. He got into fights with May quite a lot but it was always nice when they reassured that they really do care for each other.
14: Hilbert
He certainly shot up on this list. Like with Brendan, I've had a lot of ideas for him I would've added had he been an anime character. Definitely my favorite amongst the Gen V characters among the trainers and rivals.
14: Serena’s Pancham
Got to love this panda! I love how he gets shy whenever anyone praises him and how he upstaged a showcase in his debut. What you also have to love about him is that Serena only succeeded in Showcases whenever she used him. She messed up in the first one with Fennekin and her second fail was because Eevee tripped, but Pancham never messed up when it matted most. Also, another Pokémon with an awesome pair of shades. I also liked in one episode involving antagonizing Pangoro that he ran up to them to try and talk them down. One more thing, in of the contests he was batting Pokepuffs which is just cute. I’m going to miss him a lot now that the series has moved away from Kalos and Serena. Could you imagine if he evolves into a Pangoro. Yikes, might be hard to perform then.
13: Ash’s Charizard
Ash’s most badass Pokémon! Got to love how he rallied against Gary’s Pokémon. Starting off as a cute and affectionate Charmander to a teen rebel like Charmeleon to a lazy Charizard, it certainly was nice to see him develop into trusting Ash again and becoming a reliable Pokémon. Again, my favorite was when he helped beat Gary in the Silver Conference and then beat up Iris’s Dragonite. Long live Ash’s Charizard!
12: Ash’s Sceptile
It’s such a shame that he didn’t evolve into Sceptile until the end of the Advanced saga. He should’ve been ready to be Sceptile before the Hoenn League so it upsets me that yet again the anime screwed it up. However, there’s no denying that he certainly had his moment of shine in the Sinnoh League where managed to be the only Pokémon to knock out Tobias’s Darkrai. You show em the power of the grass Hoenn starter! I also loved when he was a Treecko, his battle strategy in his rematch against Hariyama.
11: Go
Wow, I already have a new favorite male travel companion. I really like his style, his goals, and his character. The creators really did a great job making up a new friend for Ash to travel with and I look forward to spending the next few years of the Pokemon anime series with him and hope he reaches his goal to catch Mew! I also find it fascinating he catches a bunch of Pokemon weekly and look forward to see how long that continues.
10: Red
Until Omega Ruby came along, Red was my most played protagonist in what was Pokémon Fire Red. Oh and he was fun to play in Super Smash Bros Brawl too. A shame they didn’t bring him back and could’ve opened the door to having more trainers as pallet swaps like they did with the Koopalings and Alph. I love looking back on Fire Red on the GBA, seems like fun memories. Pokémon is one of those series I personally don’t think it’s possible to revisit old games when you got newer much more enhanced games, but Red is definitely never going to be forgotten from those fun times on Pokémon Fire Red.
9: Shamus
Sure, Shamus was an asshole, but he was such an amusing one. He didn’t care at all what people thought and he did his own thing. I also liked his gimmick as a fire trainer and called his team the “Fire Warriors”, I thought that was a unique thing to his character. I wish he could’ve been more recurring in the Black and White series instead of being limited to just one episode. I know most fans aren’t willing to forgive him for what he did to Tepig, but in my opinion it was nowhere near as cruel as what Damian and Paul did. Shamus told Tepig directly that he didn’t want to be his trainer anymore. Damian on the other hand said to Charmander that he’d be back for him and allowed Charmander to stay in the rain knowing that it could be lethal to Charmander. While Tepig was found starving, Shamus didn’t leave him starving and it can be assumed that he thought someone would come up and untie him as soon as he was out of the area before it got to the point that Tepig was starving, and he said he wouldn’t have tied up Tepig if he hadn’t kept following him. Couldn’t it be assumed Paul would’ve done the same to Chimchar if Ash wasn’t already around? Or knowing Paul, even worse? I’ll be clear, I’m not trying to excuse what Shamus did, he is an asshole but I just don’t think he’s as irredeemable and a monster as everyone paints him to be. Like I said, I thought he was at the level of smugness and jerkass that was still entertaining. While he never appeared again, I wished he could’ve and maybe hopefully developed into a better trainer after his encounter with Ash.
8: Kenny
I could go on a rant on how much I think the anime wasted his character. He started out as a great rival for Dawn, have a good record of good showing in contests, managing to win one on screen against Dawn and they fuck him over in the Grand Festival. Unforgivable. He could’ve easily gone to the final four and have a final showdown with Dawn there. Instead he comes out of the Grand Festival and beats Ash. AFTER the Grand Festival. His development was so crooked it was impossible to understand. About his character anyway, sure he teased Dawn a lot but he was never malicious in it, and it was amusing how openly he shared the stories about Dawn. I also love how he hugged Prinplup after he won mentioned contest, it was really sweet. Other than the grand festival it would’ve been cool if he was in the Wallace Cup too, so he got screwed on that front too. You can bet there would’ve been a lot of changes to the script of the Diamond + Pearl series if I was writing it.
7: Keegan
Sixth place is pretty high for a character of the day in a filler episode, but Keegan is this high because I love his episode that much. He’s from the season 4 episode “The Stolen Stones” and I mentioned with Ramona on the other list that having an Arcanine instantly makes you cool, and he goes a step beyond that by riding one. He had a nice one episode friendship with Ash, would’ve been cool to see more of him, but of course I can see why not. I named my own Arcanine after him in Omega Ruby and leveled him up to level 100.
6: Lucas
Oh I loved playing Pokémon Diamond back in the day with the day/night cycle, especially the nighttime because of how new it was and seeing the towns bright up. Playing as Lucas certainly gives thanks to that. I enjoyed reading up on his NPC profile and thought he makes a good character to being an assistant. I certainly wish the anime could’ve interpreted that. At least he had a cameo in a movie battling Brendan, my favorite Pokémon protagonist. I definitely would’ve loved to see the two be friends. Forgetshipping is my main BROTP.
5: Ash’s Pikachu
I remember growing up I despised Pikachu because I loved Team Rocket that much, but Pikachu eventually warmed up to me. He’s just too cute to hate for too long. I mean, look at him embracing that ketchup! Everytime I’m playing as Pikachu in Smash Bros, I pretend he’s the same Pikachu. I mean, would he be this popular a Pokémon without the anime? Also, whenever there’s an episode starring him and Meowth, they’re always an instant favorite.
4: Ash’s Buizel
“Bui Bui!” I love Buizel! He’s definitely my favorite Pokémon Ash ever got. Well, technically Dawn caught him first, but you know what I mean. He always loves to fight and you can always see him training. I loved his gym battle against Waker and how he celebrated after knocking down Floatzel. I got a Buizel in Omega Ruby that’s level 100 cause he loved fighting just like Ash’s Buizel. Normally I get disappointed if a Pokémon doesn’t evolve, but Buizel is definitely an exception to those feelings. I want to see him again! I want to see him again! Bring back Buizel! He was also the first Pokémon to score against Paul in their final showdown!
3: Ash
I picked on Ash a couple of times on this list, but now I give him his honor. He’s my third favorite Pokémon boy. Sure, it’s aggravating to not see him succeed after all these years, but those feeling pass and we move on to more enjoyment. Got to love how he bonds with all of his Pokémon and how he gets along with them. Also, one of my favorite moments in the first movie was when he references the Minnesota Vikings. One of my favorite moments is when he took on the entire city of Petalburg by himself because he wanted to challenge Norman. Also, no coincidence I used a picture in his Hoenn attire. Also, Ash is number 3 on this list; Serena is listed number 3 on the Girl’s list…Amourshipping confirmed!
2: Brendan
You know by now that Hoenn is my favorite region, so it should come to no surprise that Brendan is up this high on the list. I love when the fandom portrays him with a cocky and stubborn side. I also love in the promo for ORAS and in Generations he uses the Treecko line and ends up with an awesome Sceptile! Just like how I play the games. It also gives May a Torchic just like in the anime. Speaking of which, if Brendan is my second favorite boy, and May is my 2nd favorite girl then…Hoennshipping confirmed! I probably should’ve also went with a game pic but I love this scene with him and his Treecko.
1: Meowth
Meowth is why I got into Pokémon. It also helps that he’s cute and funny. Whenever he’s set up to battle the results are almost always amusing. Who could forget the time he managed to actually knock out Onix? Also whenever Team Rocket gets sent blasting off, Meowth sometimes has the best look on his face. Meowth had his backstory shown before Jessie and James so he was the first Team Rocket member to show he wasn’t all bad. He might never be successful, but he’ll always be my favorite Pokémon character.
And that’s my Top 60 Pokémon Boys. Who knows if this list will be extended again, but for now, that’s it.
Girls:
Link to Blank: warped-dragonfly.deviantart.co…
