My thoughts on Guybrush's...
 

...nervousness about his own death. Just a few weeks ago I wrote my thoughts on it in the Trivia section of the Guybrush Threepwood article on the Monkey Island Wiki as follows:

"Until Tales, Guybrush has always wondered what it's like to die, since not only has he expected a bit more pomp and circumstance, but he has been very nervous about death and believes that staying alive is important. In The Curse of Monkey Island, for example, Guybrush's nervousness about and fear of death is expressed when the Voodoo Lady tells him that Blood Island is 'the place... where [he] will die'; it is not until he explores Blood Island that he realizes that he needs to fake his own death (at least twice) in order to find a piece of the uncursed Goodsoup family diamond ring and move on in his quest to save Elaine, thus getting over his fear. However, his fear of death has apparently returned in Tales (especially when he says that he doesn't 'plan on dying today') and is not completely overcome until the end of 'The Trial and Execution of Guybrush Threepwood', when, though mortally wounded by LeChuck's Cutlass of Kaflu, he expresses calm as he speaks to his wife Elaine in his final moments, telling her to stop LeChuck for him."

Basically, I feel that this is my opinion on Guybrush's nervousness about what it's like to die. So what are your thoughts on his apparent fear of death?

To me Guybrush didn't have as much a fear of his own death (in Tales), as to thinking it would've been rather inconvenient :)

anyone would be afraid of death but he shows ablsouty no doubts in going to blood island despite knowing hes gona die.

Well, what about the time that Bugeye says that the punishment for breaking the rule of the Brotherhood is death, and Guybrush is surprised that he doesn't want to get killed by Bugeye, Moose, or Noogie and asks Morgan for help while getting chased by them? Isn't that fear?

Or how about the time when he is hearing a death sentence being imposed on him by the judge and puts his normal hand and his hook hand to his neck in fear of the gallows before LeChuck arrives to save him? Isn't that fear too?

There's a difference between not fearing death (conscious) and not wanting to die (subconscious instinct). Guybrush jokingly says stuff like "I'll sleep when I'm dead", his "I'm not planning to die today" is more ironic than fearful, and he even tries to joke a bit as he's dying and knows he is going to die ("Kick his two-faced butt"). Heck, he even jokes when he's UNdead but receives such a big beating from LeChuck that it may as well lead to his second death. And, after all, as a pirate, he knows that death is pretty much something that may fall upon him suddenly. So, I still think he doesn't fear death.

PS. Regarding your two points (Bugeye and Grindstone), Grindstone knows how to depict a gruesome picture ;) (fear or not, it's still uncomfortable when depicted that graphically). And, as I said, Guybrush doesn't want to die and just follows his primal biological instincts when he's outnumbered. But when the odds are somewhat even, he's still cocky, still joking ("I was using that!" after a limb was cut and there was a great danger of having all other limbs sharing the same fate? Including head?)

Farlander, you said "Grindstone"... I think you mean "Grindstump".

ROFL :D
Yeah, my bad. Grindstump.

Frankly, I don't think that Guybrush ever overcame his fear of death. From my observation, people generally accept death when they know they are about to die, whether by old age, violence, or illness.

I think the survival instinct makes people afraid when death is inement.

I don't deny that they still fear it, but I believe they come to accept it at that point.

But if he dies then Lechuck will get Elaine in most cases that might be why he hasnt accepted it

I'd say that Guybrush has a healthy sense of self-preservation and fear of death, but considering all of the dangerous situations he repeatedly lets himself get into, he's much braver than he lets on. He often projects fear or even cowardice in his personality, but he either does that on purpose to conceal his intentions from his enemies or he's simply able to overcome his fears when the situation requires it.

This is what makes Guybrush such a great character. He appears to be as insecure and fearful as any common man, but he's really a hero, capable of brave heroic deeds.

I think this is one of the strangest monkey island topics yet.

admire his courage

This seems to be really over-analysing. Of course the people making the games would have the character react that way, the majority of people are scared of dying and would prefer to be alive, I wouldn't want to die in my early 20s either and I especially wouldn't want to be killed by someone else. It'd be just plain weird if you had a hero character be told that he was going to die and he just said 'Oh? Okay, whatever.'