Probably fighting the Warden way back when the game finished at his laboratory. I had unwisely invested in nothing but making myself harder to kill. I was fighting him, invited a friend over, they got ready, walked over, and after they got to my place I still fought him for fifteen minutes.
Basically, once it took me 45 minutes to kill the Warden.
Star Ocean 4 PS3 version
Ethereal Queen
Took me an entire day. i had to keep myself psyched and kept pausing as I analyzed the battle field to avoid her shockwaves and other nastiness. I had just spent hours upon hours clearing my way to her floor and didnt’ want to lose. when i finally won i was ecstatic and i immediately chose th option to e xit the dungeon and saved my game promptly 
am kind of curious whats after her floor though. i hear it ramsp up even more
One week later and I remember that there’s something far worse. Either my memory is bad or my brain tried to repress it and fail :eek:.
Anyway, White Fatalis from Freedom Unite took around 6 - 7 quests of beating on it for 25 minutes so in total, around 2 and a half hours to 3 hours. Can’t say again how many retries it took as all the successful quests were spread out over a year and a half with retries in between.
Probably Loewe from Trails in the Sky 2. I basically brute-forced him without using any buffs/debuffs (because I"m used to them being worthless in JRPGs) and it took me a good half hour.
EDIT: Oh jeez I should probably look at dates before I post. Oh well, it was still on the first page.
Ordrak in torchlight is a long fight indeed. Since I played Torchlight 2 in normal before playing Torchlight 1 and it was extremely easy , when I bought Torchlight 1 I started right at the highest difficulty. It was still an easy game until Ordrak. Not that Ordrak was hard, but super repetitive and boring. Kite, potion, spam the same spell, kite, potion, spam the same spell… I think it took me 30 minutes maximum to kill him, but I was lucky to get him stuck in some rocks and take around 50% of his health without any reaction.
I think the longest boss fights I had were in Monster Hunter Tri, including the retries. Some bosses require multiple retries to learn the patterns. Not sure which boss took the most time, but in the last one, Ceadeus, I had to restart the quest because I ran out of the 30 minute timer. Is Dark Souls hard? After Monster Hunter, Dark Souls is child’s play.
Probably log like a year ago when I was playing on my first character (pyromancer). Without any kind of help from guides or such as an inexperienced arpg gamer left me with a quite brutally ineffective weakling who barely made any damage and died pretty much in a blink of an eye.
However, in the end, after a gruelling 30 minute battle of mainly kiting and getting couple of shots on the voice of c’thon every now and then, I managed to vanquish him for the first time 
Ever since then I have had no problems whatsoever with log on my other characters after gaining more knowledge on how to utilise the classes in a better manner 
FF3/6 (depending on release version)
I had the ‘genius’ idea that, instead of fighting the Magimaster boss at the top of the Cultists Tower without Life 3 to revive from an instant-kill power it used on death, I would let it cast away all its MP until it reached zero, at which point I figured it couldn’t cast said power, and like all other enemies in the tower, would die without MP.
An hour and 50,000mp later, I was right. I may have won, but I’m still not sure if that actually qualified as a ‘victory’ in the strictest sense.
This is pretty great.
Golem Twins from Chrono Trigger…probably took young me around 2 hours to figure out all I had to do was rotate what elemental damage I was inflicting upon them…good times!
I read this awhile ago and finally thought of some.
NWN2 original campaign: the horrible multiple shadow reaver fight before meeting Shadow King boss. This fight the only way to make a shadow reaver die is to have your party NPC Zhjaeve or Ammon Jharro read a litany which is a special action only they have in their task bar. It is a long litany and they are non-optimized characters you probably have not spent much effort on their gear or learning how to put defenses for them. Their litany is long and they can get interrupted. Also the most severe problem is that the AI is bad and perhaps clunky controls. I never felt confident that Z or J were executing the command I had given them. And that annoyance made the reloads that much stressful. So there were maybe 3 reavers with endless AOE spells and usually my overpowered PC would agro them but he couldn’t kill them without the litany. By that point in the game you had a huge team and through each reload more and more pieces of your team would die and you are only hoping a litany finally goes through and limits 3 reavers to 2 and then 1 and finally victory. As I said the worst was that you couldn’t be confidant they would persist in reading the litany and not switch to something dumb. Horrible horrible reloads. And a perfect example of a difficulty spike in a CRPG.
I would say a lot of the problem was the AI and clunky controls of the litany. Because Dragon Age Origins had fights with a litany used in the mage tower map area but because your NPCs AI would not just start doing random shit you didn’t have to check on them 100 times each combat round and even if you needed a reload you wouldn’t pull your hair out.
Witcher 1: EE: The fight with insect queen was horrible because you had to destroy (but in this case fun and rewarding unlike above) because you had to destroy support beams and do different actions all the while not wasting any time because the queen could 1 shot you pretty easy. In the end the queen ended up crushed by a ‘cave in’ but it took a lot of reloads.
Just remembered a boss that took me over 30 minutes to beat and it was the final boss of Chrono Cross. There’s two ways of beating him: you either beat him the conventional way or you play a song. You get the best ending by playing the song.
How do you play the song? You have to cast a spell of each element in a right order. And here’s the annoying as shit part: the boss can screw up the sequence. His spells also count towards the sequence and it can fuck it up real easily. It took me between 30 minutes to an hour to finally play the song and it was after i setup my spell grid specifically for this boss.
In Dark Age of Camelot there are three realms fighting each other. Each of these realms had a dragon to fight against in the far ends of their homelands.
I was playing Albion that time when these dragons were not even beaten on every realm, not on mine. It took us hours, hundreds and hundreds of players alone to reach this open world boss and to give him a proper fight. When we won the loot distribution of the (realm-)raidlead took more than half an hour!
It was an insanely good community back then
The longest boss fight on my own was probably in TERA where I had to fight a super - BAM (the game names these types of npc “bad ass monster”). Some sort of BOSS BAM. Me, slightly undergeared and two or three levels below him. He could oneshot me with his “charge” and other skills I was not allowed to die at all. 1hour and 31 minutes i wont forget :rolleyes:
My longest boss fight was not in an RPG and took me 12 hours with a group.
Longest ARPG fight the boss at the end of dungeon siege 2 on the highest difficulty. Took me 3 hours. That boss was insane and I was new to ARPGs.
The longest was a failure I fought the ruby weapon on final fantasy 7 and attacked the tentacles (my mistake ) and used 99 elixirs before dying .
My wife when she asked me if the dress she was wearing made her look fat. I thought she said made her look “bad” as in, good, great. I said “Yup. Big time.”
It was probably a very short fight, because I don’t remember anything after that, just a horrific CLANG sound, and then darkness.
It was years, I mean YEARS, before I was finally able to prove something to her. My first colonoscopy. I got a notarized letter from my Dr. that my head was indeed NOT up there. My wife still insists otherwise.