Most irritating bosses

[Psychotic]

I was never a fan of Materia Keeper, simply because the fight was always the same. He'd cast Trine repeatedly, murder my entire party. Cloud would be the only one alive, and he'd get a limit break instantly. He'd bust out Cross Slash, paralysing Materia Keeper for one turn, which Cloud would use to heal himself. Rinse and repeat.

No matter how many times I've played the game, it always go down this way. It's not a hard fight and I'd never die, it was just kind of boring.

[Hollycat]

By the time I'm to him i usually have Climbhazzard or something better and finish him off pretty quickly.
For me the annoying boss was always the two headed dragon. Hate that guy.

[Jinx]

Demon Gate!

[Psychotic]

Oh yeah, smurf that guy. As a kid I never made back up saves, so my main save was right before battling him and underlevelled, and no way to go back out of the Temple and train. I had to restart my game. Four times. I didn't learn from my mistakes!

[Madame Adequate]

Demon Gate and Carry Armor have always been the biggest bastards for me. Some elemental prepwork takes care of most of the other tough bosses, but I often have trouble with Demon Gate and I almost always have trouble with Carry Armor even when I'm so ready I trout lightning.

[Jiro]

Yeah, that double headed dragon smurfer. Also, Lost Number can be a challenge if you try to hit him asap. smurfing laid me out like a dusty jam-encrusted carpet the first time I met him.

[Slothy]

Yeah, that double headed dragon smurfer. Also, Lost Number can be a challenge if you try to hit him asap. smurfing laid me out like a dusty jam-encrusted carpet the first time I met him.

These pretty much. Been a long time since I played the game so maybe I'm missing some, but those two are the big ones I remember.

[Psychotic]

Yeah Lost Number was a bitch too, though I guess it's probably because we all fight him when we first get to Nibelheim. I remember reading somewhere a very long time ago that the designers never meant you to do that.

[Slothy]

Then the designers were idiots because obviously everyone was going to do that.

[Jiro]

As if you would pass up a chance to get Vincent and that materia (Odin? Whichever summon.)

[Psychotic]

Given that Vincent is meant to be a secret hidden character, I guess they were a bit naive in thinking he wouldn't be common knowledge!

[Slothy]

Might have helped if they'd realized that Strategy Guides are things and they're usually released at the same time as the game.

[Polnareff]

None of the bosses are that bad, really. I think this and VI had the easiest bosses overall.

[Loony BoB]

Demon Gate gave me the most trouble. Lost Number was easy for me due to ChocoMog having a Stop aspect to it, and LN was susceptable to that. Beating up a boss that is stuck in time... no problem.

EDIT: Oh, and I really struggled with Sephiroth the first time I played this game.

[Jinx]

Materia Keeper. Oh, Materia Keeper. I forgot about you. Probably blocked you out, really.

So, the first time I played-played the game, I was 14. I was severely underleveled, as I never wanted to fight, but do the fun stuff and see scenes instead (this has changed about me since then.) I got to Materia Keeper, after an absolutely HELLISH time through the Nibelheim Moutains. Then, right before I could get to a save point, Red XIII died. The problem? All of my characters were out of MP and I had no Phoenix Downs. But hey, I had a Tent! As soon as I got there, I used it...but Tents don't heal people from KO. trout. Well, I traded him out for someone else, but all of my other characters were in extremely low levels and couldn't survive Materia Keeper. And I had no Phoenix Downs...I decided to backtrack instead and go back to Nibelheim and buy more Phoenix Downs, but I couldn't make it there, because my characters couldn't live long enough to get all the way back down the mountains and through the trail.

Oh, and I only had one save file.