Does any adventure game protagonist need less introduction than the plucky little pirate who could, Guybrush Threepwood? Voiced by Dominic Armato, figurehead of this proud genre for over thirty years, equal parts buffoon and persevering genius, Guybrush is to adventure games as Disney is to the movie industry.
That’s perhaps chillingly apt, since the House of Mouse now owns the poor guy and, of course, refuses to do anything useful or entertaining with him, nor the wider Monkey Island cast. It’s a crying shame, given the legacy of both these titles and of the character.
Bah… let’s not depress ourselves ahead of the musings to come, hmm? I want to share my theories on the history behind Guybrush’s rise to fame!
Threepwood’s origins — but not as you know them
Everyone knows the urban legends about how Guybrush Threepwood came to pass. The original Secret of Monkey Island was a pirate themed adventure game created through plenty of inspiration from swashbuckling tales of yore, and originally conceived as a serious piece until the superb jokes and witticisms laced throughout dialogue by Tim Schafer and Dave Grossman became beloved enough to stick.
Guybrush too is said to have been named through a combination of a pen and paper roleplaying game character, Threepwood, and the file extension of his default ‘Guy’ spritework by Steve Purcell and the art team — Guy.Brush became Guybrush almost organically. Thus the legend was born.

But I’m talking today about his origin story, not the real world tale behind his foundation. Guybrush is a loveable rogue, a consummate thief, a hapless wally capable of talking his way into all sorts of nonsense and finding his way out of it again through a combination of cartoon logic and upbeat bloody-mindedness. He’s a surprisingly fascinating character, yet one whose actual origins are incredibly mysterious.
Is there any point ruminating on the origins of a comedy media protagonist?
Nobody could blame you for thinking that — the Monkey Island games haven’t ever exactly been historically accurate to the letter, nor have they ever demanded the player takes any of their abundant monkeying around seriously. This is what makes them so timelessly comical and beloved, no?
Yet if you trace the arc of the Monkey Island series and the characters within it, there is a surprisingly solid continuity — the odd retcon aside — to these games. Characters grow and change, and not just because LeChuck is forced to reincarnate in a different undead form every time he is trounced.
Over his years of adventuring, Guybrush goes through several changes, and not only in appearance, from egotistical overconfidence to hapless, earnest buffoonery to a fancy-coated governmental figure, and then a celebrated adventurer shrouded by myth in-world come Escape and Tales.

Where do you think you’re going, fancy-pants?
The way Guybrush is first introduced to the player in Secret of Monkey Island is wonderfully succinct. It encapsulates who the player is controlling and what their motive is in one sentence.
“I’m Guybrush Threepwood, and I wanna be a pirate!”
Tack on what we learn about Guybrush as we adventure through his games over the years, and you get a good idea of who he is. He is wistful for his parents, but unsure of their whereabouts or even if they’re alive — to say nothing of the Big Whoop mind-frell linking Monkey Island 2 and Curse.
He’s in his late teens to early twenties during the beginning games, but lies about his age often enough to make this tough to pin down — it’s generally agreed that Elaine is a few years his senior.
He’s single minded when he sets out to do something, either through a secretive inner well of confidence and self assurance, or through being so dim he simply doesn’t know when to fold his hand and leave the table. Either way, this perseverance is one of the arguable reasons behind his success.
But where did Guybrush come from?!

During the events of Curse, throwaway lines reveal that the Monkey Island series takes place during the 1600s — the earlier days of piracy, but also often regarded as its golden age in the Caribbean at large.
Granted, the presence of Grog™ vending machines and other anachronisms means we needn’t pay this sort of thing too much attention, but against that backdrop, my headcanon of how Guybrush came to be on Melee Island for the first game’s events to even take place begins to find form.
Guybrush is writing his memoirs at the strangest of times during the introduction to Escape From Monkey Island. Through this, he elaborates that not only did he wander in to bug the lookout of Melee Island Town in Secret of Monkey Island from nowhere, but that he actually washed up on the beach of the island before doing so.
Astonishingly few people wash up on tropical beaches on purpose, because that’s what ships are for — and those hurt less and have slightly less risk of drowning you.
Guybrush washes up alone with nothing but the clothes on his back and, according to the cutscene, an overwhelming urge to leave whatever life he came from behind to become a pirate.
Melee Island is under the thrall of LeChuck come the events of this first game, with every pirate on the island too afraid to take to sea for fear of the terrible ghost pirate now plaguing the waters.
However, one thing that stands out to me every time I replay the first Monkey Island is that LeChuck’s long suffering lackey Bob sees fit to inform his evil master and captain that Guybrush has washed up on Melee at all. In fact, he tries to downplay Threepwood’s sudden appearance as ‘probably nothing’, even though both characters interpret it as something more — an event worth keeping a close eye on.
“There’s nothing like the hot winds of Hell blowing in your face!”
The Ghost Pirate LeChuck, during a moment of downtime that wasn’t to last
Throughout the first game, and the series at large, Guybrush isn’t taken very seriously. His outfit alone is derided, some saying he looks like a flooring inspector, others calling him “fancy pants” or other colloquialisms used to denote a weedy little fop.
I believe that’s because Guybrush Threepwood was a weedy little fop — a noble’s son or merchant family’s scion turned victim of fate!
Guybrush never speaks on his past pre-piracy, but that just makes wondering who he was before coming to Melee Island all the more fascinating! And I think the reason he washes ashore alone is because he’s the sole survivor of a ship crossing the Atlantic from Europe that was set upon by pirates — perhaps LeChuck’s spectral own.
My theory is that Guybrush was the son of a merchant family or noble house who had set out for the Caribbean and the Americas during the 1600s, only for them all to perish — bar Guybrush himself.
Growing up a privileged child in, indeed, fancy pants, Guybrush would never really have known hardship, nor the concept of not getting his own way — which is why whenever he’s shown any obstacle in the games, he persists at overcoming it with such tenacity he really doesn’t seem to have any concept of not getting the end result he hopes for. It’s all he’s ever known.

You know those moments when you lose a game or get taken down by someone’s comeback so brilliantly you feel a perverse sense of admiration? I think Guybrush felt that when he washed up on the beach, the sole survivor of the pirate attack.
All his life, his estate has provided for him, and further money was to be made across the sea in the New World — all effortlessly dashed by some choice cannon fire. In a blend of trauma and morbid respect, how could a spoilt brat like him ever expect to do anything but endear himself to the idea of becoming a pirate — the one thing he ever faced that ever bested him and his family?
“I wanna be a pirate….”
Threepwood’s newfound raison d’etre
Guybrush never found out if his parents survived the attack, leading to his lingering curiosity about them during the earlier games. He wanders the island with a single minded daze and a simple mindset that no pirate takes seriously — yet can’t help but charm the otherwise cynical and no-nonsense governor of Melee Island, Elaine Marley.
No pirate gives him any respect because he’s just some kid in a silk shirt and pantaloons with delusions of doubloons and debauchery. Yet again, LeChuck and his cronies seem to mark his arrival on Melee with hesitance — as pirates still active in the Caribbean, they may well be aware of the Threepwood name from Europe, and realise that they’ve attacked a family of consequence. That’s why Guybrush’s presence stirs such pause in the otherwise unflappable LeChuck — before the pair’s shared infatuation with Elaine drives the real wedge between them.
As the games progress, and he becomes a self made man through having been handed a clean slate and a fresh start from fate, Guybrush develops into his own man — a lover of freedom and an unlikely hero to the freebooting society of The Caribbean.
But, that’s just a theory… an adventure game theory…!
We’ll likely never learn the origins of Guybrush Threepwood, because he likely will never need any. But I can’t help but have my mind wander into just what kind of person washes up inexplicably on a Caribbean island and determines piracy and trying to marry the local politician is the best course of action. I think he was a kid from high society who got handed a reset button by the fates, and used that to become the very thing that first rewrote his life in the first place.
What’s your take on the strange tale behind Guybrush Threepwood’s rise to glory?
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