The World Ends With You. I decided to play on level one through the whole story on ultimate difficulty. It wasn't that hard up until the final boss. That thing kicked my ass over and over. And I still had to fight him even more after that to get his ultimate drop. The drop rate was a high as I could get it because my max level was the star.

Ah, my first pokémon game. Pokémon Platinum. I was a smol Cait at the time, so I made silly choices. Like naming my Piplup... Water.

I ran into trouble by the second gym. The grass gym. Water got destroyed. Now, the sensible thing to do would be training up my starly.

Instead, I grinded Water up into a level 38 empoleon.

Keep in mind, the gym leader has pokémon in the low 20s.

And then I proceeded to steamroll most opponents with my overpowered empoleon. The end.

If you thought young you was bad at naming unnamed my first Tepig, pig.

*I named

Yeah, kids are bad at naming. My lucario from the same game was named Fighting.

Also, I kept Bubble on Water for a long time... because I hated Bubblebeam's animation. Sams with Peck vs Drill Peck.

The final boss of The Legend of Heroes: Trails in the Sky First Chapter was probably the longest war of attrition I've had to have with a boss. I was only one level under the max too I think, so it was just some really bad rng I think. A friend of mine was watching and didn't think I'd make it once I started getting caught in a loop of: A character dies, I revive them, they get killed immediately afterwards before I can heal them more, heal remaining characters, try reviving again, repeat.

Ah yes, that's an annoying sounding fight, Delta. Reminds me of a fight with a DeSu boss created by bad luck...

Babel isn't that hard. It's just that the first time I got him down to form 2, everyone else was dead within a few turns. So it was just me. The only reason I lasted so long was due to Sharosha's Blood Wine+Shield All. Oh, and my anti-all set with Drain and insane Vit and Mag. I actually Drained most of the boss's MP and took him down to half health before dying. Attempt 2 was much easier.

Amazon Pandora from Kid Icarus Uprising, my favorite game of all time.
For being one of my favorite Chapters in the game, Amazon Pandora is a hell of a boss fight. On my first playthrough I kept dying and dying, until I eventually won at a lower difficulty. I'm replaying the game now, so hopefully I can redeem myself and beat it on something higher.
Oh, and Heart of Hades from the Chapter after it is a big pain too, possibly even more so.

Heart of Hades. I still hate that thing. Its corridor-based fighting and fast movements made it a pain. I don't remember much about the fight itself, but it brings back bad memories. I'd say it's my least favorite boss in the game.

God I can't believe I forgot about Babel in DeSu 1. The first attempt is always so bad with that because you can't reasonably expect to have to fight all the Bels and Babel twice in that final segment. I made it to the last phase of Babel and got it like a quarter down before it was game over. I needed to grind more and have some better demons. Drain is ridiculously OP, and I just put it on a bunch of demons with Samarecarm to never worry about characters dying again. Second try was easy street.

Not sure if I said this already, but lemme tell you about The End from Lost Dimension. Insane HP, high damage, range guarenteeing a counterattack from him... And he has powerful skills and can create clones. A few things to note:

-He's not immune to status effects
-There can be multiple status effects at once
-Sojiro gets a skill that adds status ailments to regular attacks
-A bunch of people get status stuff too

The boss literally couldn't do anything when I realized this. I almost felt sorry for him.

Gateway to Hell - Last Remnant

I can't remember much other than if you don't beat it fast enough, you lose. I'm bad at war games dammit! Don't give me a dumb timer boss too!

Darth Malak from Star Wars Knights of The Old republic had a really hard time defeating him

Another tale, this time from Golden Sun: Dark Dawn.

Went through the game, at the final boss.

Hype is real.

Go into battle.

As soon as Young Cait sees that the boss attacks thrice in one turn, she nopes the heck outta there.

To this day, the game is still not complete.

Darkside original kingdom hearts. Young me thought oh it has Disney expert mode won't be that hard. I was stuck on the dark side boss on the beach for days. Keep in mind I was really young at the time.

bump for anyone who missed it

I swear I face the wrong boss at the wrong time all the time. I was at the club in persona 4 and I was facing the boss. My dad walked in just in time to see shadow Rise transform into boss form. I have yet to actually play persona 4 since.

Running out of bosses on my end...

Oh yeah, there's Belzaboul or however you spell it from DeSu! I beat him on my first attempt, although a lack of preparation made the fight annoying. Not only could I only hit him with Almighty, but the fly units were a pain. Oh, and his insane health regen. The protag was literally the only one alive at the end. Oh, and a Mitama got experience for some reason.

For me at least it was Sully from Dead Rising 2. This mofo literally manhandle you everything you go try to melee him so I have throw like chairs, umbrellas, food, and other stuff so I could do like one sliver of his health. (BTW Dead Rising has no modes to play but still).

Pokemon super mystery dungeon. I believe it Was The seismatoads? I'm not 100% sure. Anyways, on my first run, they beat me to the moon and back. I literally reset to change my partner. I was using a Mudkip and cyndaquil at the time, so I changed to Mudkip and snivy. It took a while, but I beat them on the second run.

Also I definatley had worse nicknames. Though I might as well do a mainline Pokemon game. Black 2. The black kyurem fight. For some reason, I didn't get the memo that I couldn't catch it. Young me was also stupid. I kept trying to throw a master ball since it would give me a level 70 Pokemon, when everything I have is only level 50 or so. I almost got rent. But my Absol that I got from a friend since I asked him to train up my snivy was some egg how level 100 at the time, and ABSOLutley destroyed him.
I couldn't help myself with the joke

Rekt not rent.

Also in case your wondering my snivys name was Luigi.
Luigi.
LUIGI.

Its better than naming a Tepig pig