April Fools' Day: A couple years after Escape but well before Tales was even in planning, a couple large fan sites began an elaborate, months-long prank where they promoted a fictional Monkey Island 5 complete with "leaked" concept art and audio clips of some of Guybrush's dialogue (including a fictional fake blooper reel), voiced by Dominic Armato! It culminated in a clip of Guybrush talking to the "Little Lechuck" and "Little Guybrush" puppets from Escape...
Guybrush: Hey, Little Lechuck, will you be my Valentine?
Little Lechuck: What are ye, daft? It ain't even Valentine's Day!
Little Guybrush: That's right, it's April 1st! And- hey... does that mean all this Monkey Island 5 talk was an April Fool's joke?!
Stan in Escape from Monkey Island, and yet again in Tales.
Carla and Lemonhead in the Special Edition of Secret (S. Scott Bullock, who had voiced the latter in Curse, now voices Red Skull in the aforementioned Special Edition).
The Voodoo Lady in Tales.
Elaine is an odd example of this trope coming full circle and actually reversing itself. Also, she is the series's most obvious example of this trope because not only does she change actresses, but she (inexplicably) changes accents as well.
In Curse..., she is voiced by Alexandra Boyd and has a British accent.
In Escape..., she is voiced by Charity James and has an American accent.
In Tales..., she is once again voiced by Boyd and once again has a British accent. Also, Boyd plays Elaine in the Special Edition remakes of Secret and Revenge, which among other improvements add voice acting to the previously silent originals.
Promoted Fanboy: Dominic Armato was a huge fan of the first two games, and would tell his friends that his dream project would be voicing Guybrush in a third game, which at the time seemed unlikely to be made. When he was called in to audition for a part, he didn't know what he was going in for at first, and when he discovered what role and game it was, he says he nearly fainted. His sheer enthusiasm and love for the series won over the creators and got him the part. His wonderful performance as Guybrush in the third game and subsequent installments (and the remakes of the first two) is one of the only things the Broken Base seems capable of agreeing upon.
Turns out an animated film of Monkey Island was planned. However the scripts that were made for the film would later be used for The Pirates Of The Caribbean movies. It is unknown if this would have been good or not to prove that not all Video Game Movies Suck.