Dark Sun Gwyndolin
Skills: Rapid fire*, Massive soul spread*, Energy ball*

Times died on 1st playthrough: 5-ish

This boss is completely optional, and its actually recommended that you do not kill this boss in many cases. However it is my belief that you should kill this boss whenever you can during your playthroughs (he is an asshole). There is no reason not to actually, unless you want to stay committed to the "Blade of the Darkmoon" covenant or the "Princess Guard" covenant, in which in these cases, you should completely ignore this post. After you take the Lordvessel, kill Gwynevere and Anor Londo will go dark, leave and take the center elevator down to face this boss, who goes by Dark Sun Gwyndolin.

Wait wait...Gwyndolin as a girl with boobs? I APPROVE!

In many cases, Gwyndolin isn't a very tough boss, however the trick to this boss is that if you're hit once by ANY of his attacks, you're either dead or you will take a crap ton of damage. Each and every one of his attacks can kill you, but the thing is that he has only 3 attacks you need to watch out for. Still, as I said, his attacks are nothing to sneeze at, and chances are you will either kill this boss unscathed, or you won't kill him at all. Also since he is known as a feminine guy, he fights like a girl, and its very common for you to be pissed at times.

Rapid fire*- He rises a little bit and shoots a few darts/arrows at you. This one is simple, block everything. However, if you are hit by everything, chances are you that you are already seeing the "YOU DIED" screen. It hurts like a bitch, so please do block it.

Massive soul spread*- He disperses a huge bunch of soul arrows that float around him for a mere moment, then sends them all towards you at a quick speed. Dodge them as they come to you, don't bother blocking.

Energy ball*- Probably the only attack that will NOT one shot your ass. Still, its probably the attack that is the easiest to get hit by. Its fast, and it comes out incredibly quick. Dodge this one.

Fighting this guy is not that complicated, although he might catch you off guard during your first few attempts if you don't know what you are doing. His attacks hurt big time, and have the potential to one shot you even if you aren't running a full glass cannon build. Also, this fight is a dodge fest. You battle against Gwyndolin in a long deserted hallway with pillars at the side. You have to avoid his attacks as you approach him at the end of the hallway, and when you finally reach him you get to hit him for abit before he teleports further down, then you have to repeat the whole process again.

Die pussy!

As you can already guess, this whole process is incredibly annoying, especially if your character isn't built for doing massive damage. You'll have to dodge and run to him over and over until he dies. Getting to him is the issue since he tosses attacks your way. Lets go through his attacks, I label all of his attacks as special since all of them have the potential to kill you. Rapid fire is the first one, and this is the attack you have to worry about the least. He rises a little bit and sprays some darts/arrows at you. Blocking all these can suffice, but if you don't you're probably screwed.

Massive Soul spread is the most annoying out of the 3, as it can be easy to mistime your dodges and that will get you killed. This attack hurts like a bitch, and may one shot you depending on how many of the arrows you are hit by. Blocking these will reduce the damage taken, but its not worth as it still takes quite a good chunk off your health bar. Note that this attack and the rapid fire attack can be completely avoided by ducking behind pillars, though this will waste precious time which can be used to advance forward to him.

His final ability is the energy ball, which is the least damaging of his abilities, but will still hurt like a bitch. Its the attack that will catch you off guard the most, since it comes out incredibly fast and there's almost no indication of that attack coming. You can't block this and it will still get you even if you're hiding behind the damn pillar. So what do you do? Whenever you see a blue flash appear from Gwyndolin, just roll away, you don't want to get hit. 

When you finally get to him, you get to hit him for awhile, before he cowardly laughs at you and teleports further away from you, then you have to do everything again! Doesn't that sound like fun? Fortunately, he doesn't have a lot of HP, and since he only has 3 attacks, you can easily adapt to his patterns and eventually learn how to counter him. It did take me awhile to get used to his attacks though, and that cost me my life quite a few times.

Yeap, this is as feminine as guys can get.

As you can see, Gwyndolin isn't a complicated boss to  beat, but he sure is annoying to play against. He shoots at you, then as you get to him, he teleports away. He isn't exactly fun to fight, and when you beat him you get 40000 souls. You'd also have to betray the covenants as I said earlier, so seriously, this guy is pretty optional, though I have gotten the habit of fighting him everytime I have the chance to.