I've played Kingdom Hearts for a long time as my first KH game was KH2 all the way back in 2007 but that game most definitely had the most frustrating bosses I fought throughout my childhood. Keep in mind as you read through this that I was HORRIBLE at video games during this point in time and I could only play video games in certain parts of the day which will explain what I'll be trying to say (remember that as a kid?) so feel free to question anything. I believe the first boss in KH2 that I had a really tough time with was (drum roll please) Demyx, no big surprise there. Except that it's not the Demyx your thinking of, it was the first time you fight Demyx in the Underworld of Olympus Coliseum. I know I know, how could I possibly for such an easy boss get completely stuck on Demyx? Honestly I don't know either. I don't think I realized how important the Triangle button was for that fight so that's a big reason why. Oh and I didn't beat the boss for about 4 months, let that roll in your head for a sec. Next boss that I absolutely hated was the second phase of Demyx which is an obvious fact among longtime fans. Except this was the point of the game where I finally realized I can change my Keyblade. Yeah I think that would've helped me a LOT. It took me about 6 months to beat Demyx here so that was a deep hell (I can imagine myself crying if I died during the section where the FF characters help out, thank GOD that didn't happen). Next was Xaldin in Beasts Castle and that one took almost as long as Demyx being about 6 months. Xigbar was also a pain in the ass since it took me even longer for him to die making it 8 months or so. Siax was AGAIN a even more pain in the ass as I could not figure out on how to beat him but I eventually clocked him making it around 6 months. and lastly Xemnas Final Form where it took me about 10 months to beat his ass and FINALLY watch the credits. I remember crying tears of joy once I finally beat the game and got to hear Sanctuary after the Battle for the first time. and I all did it under the Beginner Mode difficulty, truly a marvelous accomplishment. *cries of intense embarrassment* But what bosses in KH2 or the series in general took the longest for you? I'm pretty sure it was a lot faster than it was for me (and under a harder difficulty lol)

Edited June 26, 20178 yr by Finn and vigor

Clayton was especially annoying when i was a kid.

Probably Dark Riku. It feels so easy now, and maybe I was just underleveled, but there's a reason the prior cutscene is engraved in everybody's heads. Xaldin, similarly, was a royal pain but again one I think is easier to deal with now.

 

Cave of Wonders was always a bitch, though, and I still feel like that's true =P.

Edited June 26, 20178 yr by BlankShell

Clayton and Ansem Riku in Kingdom Hearts 1 they where a pain.  For some reason I could never beat Final Ansem on Rikus Side of Chain of Memories for the GBA but he's easier on the PS2, PS3, and I'm assuming the PS4 version as well (Haven't played the PS4 version yet). I didn't really have any problems with any of the other bosses in the other games save for the secret bosses.

It probably took me a good 30 minutes to an hour to defeat this dude. That is, if I didn't die first ._.

To be honest, when I played KH II for the first time when I was like 6 or so, I literally cried because I couldn't beat Demyx! I thought the fight was so unfair

Honestly, I don't remember exactly what the /hardest/ boss to beat for me was, but larxene from re:CoM is etched into my memory as hugely frustrating and difficult.

It probably took me a good 30 minutes to an hour to defeat this dude. That is, if I didn't die first ._.

oh god yes! It was like trying to catch a oily ball with oven gloves on Ice

To this day, Lingering Will still takes a lot of tries. Especially now with 2.5 and my ridiculous OCD need for a "perfect" fight, for some reason his AI has changed slightly, there are times where it doesn't mix up it's move set a lot, there was a few attempts where all he ever did was that Rising Sun-like attack and it got real annoying. So I guess these days it's not so much that he's just difficult, but it's both that he's difficult AND I'm a stubborn as hell perfectionist now (for the record, I blame DBZ, I got too used to everyone showing off their moves...guess I should blame Captain Falcon too, lol). But yeah, I guess Lingering Will and Mysterious Figure always give me a understandably hard time, though I guess as far as a regular boss fight goes, KH1 Riku and ReCoM Riku Replica and Larexene frustrated me much more.

KH2 Xigbar battle..

 

I always kept dying at the part that he says: LETS SEE HOW YOU DANCE!

 

And then I got stuck in the arrow rain and then the game over screen appeared.

 

Also final Xemnas took a long time to beat.

 

I didn't know that you need to press X with the bullet rain to deflect it with Sora. I only pressed Triangle...

One of the Repliku battles in Re:CoM annoyed me a lot, and I remember taking a while when fighting Dragon Maleficent in KH1.

 

Leechgrave was Awful, but I was a teenager by then.

It probably took me a good 30 minutes to an hour to defeat this dude. That is, if I didn't die first ._.

Oh. well I beat him way faster than that! yeah! (remembers the 3 years of pain fighting that damn Bird). I'm not kidding, it took me YEARS to beat that Damn Ruler of the Sky.

Oh. well I beat him way faster than that! yeah! (remembers the 3 years of pain fighting that damn Bird). I'm not kidding, it took me YEARS to beat that Damn Ruler of the Sky.

I was almost to the point of quitting my game for good

That annoying boss from 358 Days,Ruler of the sky I think he was call and the giant pumpkin thing also in 358 Days and Mysterious Figure in BBS because the fight is kinda bs,I didn't realised how bad this fight was until I recently fought the data organization and Terra,you can make brutally difficult fight a fun fight,but Mysterious Figure is not fun.

Oh, there was definitely a fair share of frustration among all of us when battling bosses in our younger, noob years as Kingdom Hearts fans!

 

There were many boss battles that I found difficult at the time! I think that Xigbar in The World That Never Was definitely was a true pain in the ass to beat, what with his teleporting and constant firing and all! Back then, I didn't know how to make good use of the Drive Forms, and I button mashed a lot instead of thinking strategically, so I got my butt kicked a lot! I also remember dying a lot battling Cerberus in the Underworld! There were many others that were difficult, but those two, at least, were very hard for me back then!

 

Cerberus in the first Kingdom Hearts was also difficult for me as a kid! So much so that I left that world and completed Deep Jungle before heading back! And in Deep Jungle, Clayton was a royal pain! Took me a good, sweet amount of time for me to beat him, especially considering one couldn't skip cutscenes in the first KH! OH, AND DARK RIKU IN HOLLOW BASTION! God, I remember having died so many times, having to see the same cutscene repeatedly! But since I loved the story, I didn't mind. It was still frustrating though!

 

For Re:Chain Of Memories, I think that Axel in his second encounter was very hard for me, especially when he'd perform the multi Fire Wheel attack! My God, if I didn't have a 0 card at the moment, I was totally screwed!

 

And in Birth By Sleep, Terranort was the biggest pain of all! 

 

I could go on and on!