In my opinion, the reason Hugh Jackman was a bad choice for the Wolverine role follows the same inescapable logic for the character demanding an "R-Rating" to do such a film true justice.
Wolverine was not written to fit the 'mold' of a typical clean-cut superhero. In fact, I believe he was originally written as a villain and just got popular enough to gain superhero status.
Wolverine was conceived as being short, stocky, hairy, angry and vicious - like the animal (and hence his name!). These are his defining characteristics as a character and to alter any of them would be to destroy the essence of who he is.
Wolverine is angry for a lot of reasons. His life has been defined by tragedy and pain. He is not what most people would consider classically attractive or physically imposing and therefore does not immediately get the girl or intimidate his enemies at first glance.
He smokes, drinks, curses and kills - this is not a guy you'd want to take home to meet the folks.
The problem with Hollywood is that they want to make him acceptable to a mainstream audience. Let's look at the key criteria Hollywood demand for all their heroes:
1. Tall - The whole point of Wolverine's character is that he's always underestimated by his enemies who don't know him. They just see a feral 'runt' standing in front of them who doesn't look like much. A lot of people might argue that he can't be taken seriously as a threat to the villains if he stands several feet shorter than them. Ummmm...this is why he was written with regenerative powers and an Adamantium skeleton/claws!!!! It doesn't matter how short he is because he'll just cut any enemy down to his own size. He may not be the most powerful mutant, but he is certainly the most tenacious. You can knock him down over and over and he'll just get up and keep on coming at you until he eventually wears you down.
2. Attractive - I agree that Hugh Jackman bears some basic resemblance to Wolverine as drawn in the comics, but he's an idealised 'Hollywood' version. I felt the same way when they cast Thomas Jane as the Punisher. He didn't have a hard enough face to sell the harsh, brutal and traumatic life he had lived.
Thomas Jane and Hugh Jackman are pretty boys trying to pass themselves off as the grisled, battle-damaged veterans that Wolverine and the Punisher are by working out in the gym a bit, growing some facial hair and frowning a lot. I actually felt Ray Stevenson was an example of decent casting as Frank Castle in the remake and the "R-Rating" was perfect too (shame about the film overall!).
I get the idea that Wolverine in the comics doesn't automatically draw the attention of the ladies and that any attraction they develop for him is built on their uncovering of the man beneath his unconventional appearance and salty demeanor (think Beauty and the Beast) and not because he's been cast with a heart-throb actor.
My final complaint is that Wolverine's voice is best when it's really gravelly and deep. Hugh Jackman did a passable job, but in the end he was trying to growl in a tone he just doesn't have.
I accept that Hollywood need to 'sugar' up their superhero characters and franchises for the mass market. Take the new Star Trek film - It's exciting, sexy, action-packed, epic and funny......but fundamentally it's NOT REALLY Star Trek in spirit any more. It's a crowd-pleasing sci-fi movie that's given itself the Star Trek label but lost a lot of the underlying philosophy and ideas that made Star Trek what it is (was).
But this is a totally different conversation...