Part 44: The reason it works is because interrupting DrillMan's attacks resets his position, so he gets hit twice.
I AM HERE TO DO WIZARD-TYPE THINGS AS WELLDrillMan.EXE...
Where do I begin? Honestly, this guy is one of my most hated bosses to fight in the regular game. Reasons for that include a) He's usually off screen for most of his attacks and b) Regular chips (the kind that fire straight ahead) can't hurt him.
So, yeah, dude's kind of a prick.
Anyway, Giver is the one who told me what to do for this, and it's, well...
Fucking hell.
Look, I don't know any more than you do, okay?
Anyway, AI time:
To start with, he's vulnerable for a split second when he starts the fight. After that, he jumps into the air and starts attack A.
Pictured: Attack A. Things to know about this attack - see how his drill is ahead of him? Yeah, that thing blocks all non-breaking attacks. So either you use some sort of breaking attack (I think it works, I've never tried it myself) or you try to hit him with a different attack. That was why I had those Slashers in my folder, in case the Sensor3 + "hit him with really good timing" strategy didn't work out. Only his body is vulnerable, and it's a square behind his head; with good timing, you can hit it with a wide sword or something. Recommended strategy, if you don't have the Sensor3 thing, though, is just use Slasher. 240 a pop isn't anything to sneer at.
Occasionally, he'll stop using Attack A and choose one of these two. B (the holes) is pretty easy to dodge; just don't stand in front of the drill when they come at you. I'd suggest staying in the center whenever possible just so you have more time to react.
Attack C is actually somewhat nasty. First, he breaks three panels (warning you with the yellow flashes, like always) which is pictured above, and then drops rocks on three of the unbroken panels. That means you have anywhere from zero to three safe spots, depending on how the panel breaking went. The real trap to this attack is the fact that after he finishes attack B or C, he goes right back to Attack A - that means, if you have broken panels, you can't dodge very well.
Of things to note: in regards to Attack A, I've never seen him come out third. Always first or second. Who knows, it might be useful, or maybe the RNG just really hates the number three.