Where is Guybrush coming from when he arrives at the Lookout Point at the start of TSOMI?

Before washing up on the shores of Mêlée Island [1], declaring that he would like to be a pirate [2], and making the hike to the Lookout Point seeking instruction in his chosen craft of pirating [3, 4], Guybrush Threepwood was from the Old World [5]. He had been abandoned by his parents (or so he thought; it may have been their deaths that separated them from him) [6, 7], but not before Guybrush’s mother had had time to try to get him to practice the piano, which he would later regret that he did not ever do [8]. But he was likely in an orphanage from a very young age [9].

It would become naive, young Guybrush’s life’s ambition to become a fierce, swashbuckling, bloodthirsty pirate [10]. He may have even lived on his own in a miniature-pirate-ship-styled houseboat and dressed in pirate costumes, discontent with his job, which he would have daily threatened to quit (only to not be taken seriously by his boss, of course) [11]. And during the Golden Age of Piracy in the late 1600’s, pirates were secure in their Caribbean strongholds, amassing huge fortunes from plundering shipments of New World gold; these tales of pirate wealth thus attracted Guybrush, as well as many other adventurers [5], and his travels led him – fresh from the Old World – to Mêlée Island (somewhere in the Caribbean) in a quest to fulfill his dream [5, 10].

But something must have caused the ship Guybrush was on to sink before he was able to safely reach Mêlée’s harbor in it, resulting in his washing ashore, leaving him alone in a new land where no one knew who he was or where he had come from, and with no money [1, 3, 5]. But what he did have were high hopes and an insatiable curiosity and desire to become a pirate [5, 12], though he was not yet truly aware that there was more to being a pirate than simply swinging a sword and drinking grog [10]

  1. EMI game manual: https://archive.org/details/EscapeFromMonkeyIslandManual
  2. Shown in the opening flashbacks of EMI
  3. In the beginning of SMI
  4. CMI game manual: https://www.mocagh.org/lucasfilm/mi3-manual.pdf
  5. SMI press release: https://scummbar.com/games/index.php?game=1&sub=info&todo=14
  6. Known from Guybrush’s reaction at the start of the “Dem Bones” hallucination in MI2 when his parents appear to him
  7. Based on Guybrush’s genuinely believing what appeared to be the remains of his dead parents in the Dinky Island tunnel system under a sign marked “LOST PARENTS” at the end of MI2 were them
  8. Learned from Guybrush’s comment about the piano in the Bloody Lip in MI2
  9. Based on LeChuck’s telling him in his Fortress in MI2 that, in his case, babies came from the orphanage
  10. SMI game manual: https://www.mocagh.org/lucasfilm/mi-manual.pdf
  11. If it is assumed that events eventually came to pass in his life that partly held more or less true to the information that would have been in the official Monkey Island animated movie that had been in development but never ended up getting made, even though it was of a clearly divergent continuity from the game series, since, where it does not outright contradict the story of the games (as with his being from Mêlée Island [he is clearly from outside the Tri-Island Area based on his unfamiliarity throughout the games], living with a pet monkey [which would not happen if he was not in the Caribbean already, which he was not based on the SMI press release], and working as a chum-bait fisherman [his comments to the Fisherman in MI2 indicate he had never been fishing in his life, and his fixation on the smell of the Bait Shoppe in EMI indicates he never would have had the opportunity to get used to bait as the owner of that store suggested happens when you are around it long enough]), it does provide some potential additional background for Guybrush’s character that might be argued as being the closest we can get to canonical. All movie information from: https://scummbar.com/movie/
  12. SMI Special Edition press release: https://scummbar.com/games/monkey1/mise_press_release.pdf
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