So he's at the Four Kings. Considering Phil's sole (no pun intended) boss strat in the Souls franchise is DPSing every boss (unless it's cheesing from a distance or letting an NPC do the work for him) I was thinking 'well at least he should be fine here. He's played this game a bunch of times and it's one of the few bosses where running up to the boss and hitting it as hard as you can as fast as you can is a viable and even preferable strat'. But no. Phil seems to have a dodge build with low poise and stamina and only 10 estus flasks. He's using a heavy weapon. He's using heavy attacks. Uh-oh.
He ended the stream after several brief failed attempts but it kills me and tickles me at the same time that this is one of the very few bosses in Souls where his strat of just running up and wailing on a boss while tanking damage (or, you know, using a shield to block, or dodging and resuming your attacks) is actually viable and preferable (if you have the build and weapons to do so ofc), and is usually considered one of the easiest bosses in the series and he's STILL struggling after playing the game at least 4 times I can remember.
Since Phil still doesn't know how to build stats or about things like scaling or soft caps after years playing the series he's attempting builds and strats he hears are strong but doesn't realise the people using those things (except for when they're noob cheese strats) actually know how to dodge, how to parry, how many hits they can get in without getting greedy. They know the movesets and can successfully dodge attacks so they don't need to rely on shields or higher stats to achieve a quick and easy win.
Phil is like newbies to Dark Souls who complain about how hard it is because they always do the same thing: Try to DPS, dodge spam blindly, and spam attacks until they get hit. Usually those people learn 'spamming dodge wastes stamina and can make me get cornered or roll into attacks',. Usually they realise 'I can only get in 1-2 hits safely unless the boss is doing -insert action here-'. Usually they realise that timing is really important and that if they can't rely on their timing that shields are the best way to safely be able to run in and attack and make mistakes without being too badly punished most of the time. I think the biggest virtue you can have in Souls is patience: the patience to learn patterns, the patience to wait for openings, the patience to do safe hits without getting greedy, and the patience to use reliable and balanced builds and weapons instead of gimmicky ones. Once you acquire the skillset and knowledge to play riskier builds and try riskier strategies then the world's your oyster. Until then, just learn the damn game.