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I guess I'd respect it more if it weren't from Windows 9x. He could have gotten creative with a core dump that included a stack trace, but no, he went with the toy OS.
I kinda like it, actually. I mean the idea of a passage of some kind in that computer font. The message itself it stupid, of course. I've decided not to ever get any tattoos, myself. Unless it's some kind of memorial for a loved one.
Since dude submitted a picture of it to a body modification website (the 'modblog' watermarked onto the image), it seems pretty safe to assume that he's fairly happy with it. And, as much as one can tell from the photo, it looks to be fairly well done, technically speaking. And, absent an explanation from him, I'm not sure it's reasonable to try to judge his motivations and whatnot. Maybe he used to bond with his late father over Windows crashes or something.
Granted, it's not really to my taste, but, hey, he probably doesn't like my tattoos either.