I was thinking on this a little earlier and it occurs to me that if anything is a film with some similarity to Monkey Island, it isn't pirates of the Caribbean, it's this.
We start out with a nerdy, hopeless-romantic of a stable-hand who desires adventure and love, yet to the woman he desires he can't really form a real sentence, so he has his own way of expressing himself to her.
As the film progresses, we find that Wesley's time with a pirate crew has awarded him the traits of an intelligent pirate: witty, he has a sense of flair, still a romantic, and he's rather cavalier in the face of danger.
This is almost the perfect mirror for the evolution of Guybrush Threepwood between SoMI and MI2:LR, because our protagonist went from being the rather clumsy, inept, and boring (flooring inspector, anyone?) geek that he was in the first game, to what he became in the second.
In the second, he had the traits of an intelligent pirate, much like Dread Pirate Robins did. He was witty, he had a sense of flair (and a great dress sense, too), he was still a romantic, and quite cavalier in the face of danger.
Now I feel that CMI & EMI were a reversal of that, it would be like having Dread Pirate Wesley go back to being stable-hand Wesley. He'd lose all of the wit, the flair, and his ability to hide fear behind a good sense of humour, and he'd just become bumbling Wesley again. Would anyone really want to see Princess Bride II if it was like that?
Now what Telltale have done is given us a protagonist who builds on the previous incarnations, they've given Guybrush a future. This would be like a true sequel to Princess Bride, to keep the analogy going. Dread Pirate Wesley might relax a bit, but he'd never lose the traits that made him Dread Pirate Wesley in the first place. That would make for a brilliant sequel, and one that honours the film that came before it.
And that's why I feel that ToMI is so far superior to either CMI or EMI, because it does honour the progression of Guybrush Threepwood, what we're seeing here is an evolving character. And frankly, we have an interesting, genuinely witty, and animated protagonist who's not afraid to show his sense of flair. This, compared to the static, and honestly boring Guybrush of CMI and EMI is a breath of fresh air.
There've been countless posts and threads about why people like the CMI Guybrush, some have even been illustrated, but after this analogy of Princess Bride popped into my head earlier, I just knew I had to share this with all of you, as perhaps this would help some understand why I feel the way I do about this new series.