Shaun’s Solo 2: The Secret of Monkey Island

It was right before Saint Patrick’s Day when third-grade me rose from a mud puddle with a little Guybrush burning in my heart. I wasn’t wearing green, see, and the class bully—an enormous forehead named Brett—never missed an opportunity to hassle the new kid.

We were all lined up to go back inside from recess and the teacher was lagging behind for whatever reason. Brett left his spot in the line, crooked smile on his miles-long face, and poked me in the chest. Two fingers. Rock rigid. He mumbled something about my lack of verdant clothing. One sullen retort later, we were locked in a grapple, my hair askew, his smile growing wider as he backed me off the cement onto the damp grass. My classmates were a rising chorus of a kiddie UFC crowd, but there was no real contest to be had; Brett had the physique of a fifth grader and all the mercy of a diamondback.

I remember the toes of my shoes sinking into the wet ground as a pushed against Brett with all my might. “Not…*this time*, Brett!” I grunted the instant before the miniature hulk pivoted just so and dropped me, rear-end-first, into the chilly mud. The class was already moving inside as I climbed to my feet, grime caked on my jeans and dripping in glops from my elbow. Two of my nicer classmates hesitated at the doorway, vague pity on their faces. Brett vanished inside, shaking his flat-topped head and guffawing to no one.

The righteous fire seared its way out of my throat, folks. My eyes fired daggers at his ill-fitting Eagles jersey. Justice would be mine. “And let that be a lesson to you!” I shouted. I heard a puff of surprised laughter from the nervous semi-supporters lurking by the entrance. Something like third-grade hope flickered into being.

And it all started to make sense in a way only Guybrush Threepwood, mighty pirate, could understand.

Alas, this was three years before Lucasfilm Games upstart Ron Gilbert, along with Tim Schafer and Dave Grossman, would bring the ultimate interactive piratical comedy to PCs, and help me and those like me chase that strange burst of defiant hope my mud-caked zinger ignited. I and so many others would go on to be the new kid time and again in the intervening years, so let’s step boldly into 1990 and discover the game that put wind into the sails of every smart-mouthed newcomer ever to (poorly) resist being pushed around: Lucasfilm Games’ masterpiece, The Secret of Monkey Island.

What I wouldn’t have given for a sword in ’87. Or at least a necklace of eyeballs.

THE GAME: The Secret of Monkey Island was Lucasfilm Games’ fifth of five early point-and-click adventure games. It was the culmination of the team’s efforts to compete with powerhouse developers like Origin and Sierra Online. Firmly detached from text-based or even keyboard-reliant games, and evidencing Ron Gilbert’s distaste for high fantasy, Monkey Island is a swashbuckling adventure set in a fictionalized Caribbean island chain thick with calypso music, grog-swilling privateers, genteel Island cannibals, and voodoo-powered intrigue. Did I mention that it’s funny? Because IT IS. Really, *really* funny.


We step into the pristine, buckled shoes of foppish klutz and preternaturally charming Guybrush Seepgood Threepwood, a young and fresh face new to the islands. And new to adventure, too. And talking to girls. And…well, look, let’s be honest: he’s new to just about everything. But the guy is nothing if not eager. Disarmingly so. In fact, his entire quest is laid out in the first line of dialogue. Startling Melee Island’s spectacularly near-sighted lookout, our hero proclaims, “Hi! My name is Guybrush Threepwood, and I want to be a pirate!”

There ya go. The plundering is afoot!

Threepgood Threepwood soon meets with the local pirate leadership (read: foul-smelling, grog-swilling pigs) and learns he must pass three trials to achieve true piratehood: sword mastery, thievery, and treasure hunt…ery. Ahem. Along the way, Guybrush meets a terrific supporting cast of ne’er do’wells, cheats, crooks, and scallawags. Before long, our wet-behind-the-ears hero manages to fast talk, hoodwink, and improvise his way into achieving goal after goal only to find his love interest kidnapped by the fearsome local undead menace, the ghost pirate LeChuck. Thus begins the true adventure. With the villain’s spectral ship vanishing into the mist, Guybrush must quickly procure a ship and assemble a crew before setting off to rescue his beloved Elaine from LeChuck’s hidden lair beneath the eponymous Monkey Island, a place from which few ever return.

Ah, the Scumm bar. The perfect place to find some role models.

We navigate all this by moving Guybrush where we wish via a simple cursor, and clicking one of a small selection of onscreen verbs to tell Deepwood Threepwood how to handle items, individuals, and his environment. Wit is the currency of this game, so brain power and a keen sense of humor are required to find solutions to the game’s clever puzzles. Faced with a troll blocking a critical bridge early in the game, Guybrush is told the monster will only yield if the young wannabe man of fortune offers an item that could “attract attention while having no real importance.” And waaaaaait a moment. What’s this: that red fish behind the town’s bar…is that…is that a *herring*? Oh, you clever, clever adventure game.

Ooooh, adventure game industry burrrrrrn!

Add to this brew some voodoo recipes Guybrush will never have the *actual* ingredients for, literal-minded cannibals willing to trade an enchanted head for something resembling the means to make a new one, one very useful rubber chicken with a pulley in the middle, and a game valuing cleverness over fast reflexes or intricate button combinations emerges as a gleaming gem of an experience.

WHY IT’S GREAT: As many fans of adventure games of the 1980s and 90s can attest, death tended to punctuate (and hinder) adventuring progress quite a bit. Type USE MUSHROOM instead of GIVE MUSHROOM? Dead. Game over. Look too closely at that alien creature? Dead. Hope you saved! Forgot to note that minuscule bit of evidence 10 gameplay hours ago? Dead. And STUCK. Have fun restarting from scratch!

Oh, but not so in The Secret of Monkey Island! Gilbert, as frustrated as the rest of us with late-20th-century perpetually-mutilated adventurers, refined his no-death policy previously seen in his earlier “Maniac Mansion,” to also avoid un-winnable situations in Monkey Island. We are free to wander, ponder, and experiment to our treasure-hunting heart’s content in our unkillable state. The troll from earlier threatens us with an ultimatum, for example. We’ll get THREE tries to give him what he wants before he devours us, ending our quest right quick. But after a fourth, fifth, heck, even a *twentieth* incorrect attempt, his threat descends into deeply comical territory and we soldier on, offering wrong item after wrong item if we so choose. In one fantastic sequence high atop a cliff on Monkey Island, Sheepstood Threepwood can walk to the edge of an outcropping only for the rock to plummet from under his feet, sending Guybrush tumbling, a la Wile E. Coyote, to his doom. Or not! Even as a Sierra-esque “Whoops! You died!” window pops up, prompting us to reload a previous save, our hero rebounds onto a stable spot on the cliff. He looks into the “camera,” nonplussed. “Rubber tree,” he says.

Fourth wall?? We don’t need no stinkin’ fourth wall!

And yes, there is ONE way to actually perish as young Master Fleekhood Threepwood, but A.) it’s so well-hidden as to require players to put forth effort into finding it B.) it’s comic gold getting to that point and C.) I *really* want readers to play this thing…so I won’t mention it here except to say it will take some concentrated…waiting.

Point being, The Secret of Monkey Island is about *fun* for the witty types out there. Go figure, right? We get to win; it’s a matter of when, and—thanks to some outstanding humor in the dialogue we choose—just how funny things get along the way.

THE EPIC SCENE: While there are SO many absolute classics to choose from here—braving “The Monster” in Meathook’s high-security pen, the climactic air & ground battle with LeChuck, the amazing off-screen battle with Sheriff Shinetop told through cartoon sound effects and a menu on autopilot—one sequence stands head and shoulders above the rest.

One of Guybrush’s earliest tasks is to master sword-fighting, and the only way he can do this is by managing to out-duel Melee Island’s own Sword Master. Even locating this enigmatic figure is a bit of a challenge, and finally finding her isn’t enough; sans training, she won’t even bother humiliating Guybrush.

So we find ourselves a trainer and the true genius of the gameplay mechanic emerges. As our grizzled, cigar-masticating teacher tells us, swinging a sword around isn’t actually that important. No, what *matters* in a pirate sword fight…(can you feel it coming??) are one’s wits! Insults, it turns out, are the difference between true Pirate Lords and lowly swabs around these parts.

What unfolds next is a brave bit of game design Ron Gilbert himself has expressed some small insecurity about: Guybrush must wander the island, waylaying any stray pirate roaming the roads and challenge him to a pirate duel. You’ll recall that death is not an option, and so we have nothing to lose but Guybrush’s pride as he fails again and again to dish out biting insults and weather barbed retorts. Over and over he is disarmed by ruder, cruder toughs, failing to Errol Flynn his way through clashes of steel and sass. And yet, as defeats pile up, Guybrush commits the savage burns he hears to memory, turning them against his foes in later matchups. After a time, he starts winning a few of these exchanges. “I’m rubber, you’re glue” gives way to far smarter fare. And the insults themselves are outstanding—and they ought to be, as they were written *specifically for the game* by Orson Scott Card of Ender’s Game fame.

“Have you stopped wearing diapers yet” is met with a crushing, “Why, did you want to BORROW one?” And opponents stumble when Guybrush presses his advantage: “My handkerchief will wipe up your blood!” Sheepshood Threepwood hisses, his saber raised in a jaunty pose. “I’m shakin’, I’m shakin’” stammers the overconfident victim, clearly forgetting the proper riposte (“So you got that job as a janitor after all!”, of COURSE), and *whip-fwoosh-thud-d-d-d*! Guybrush flicks his opponent’s sword into the dirt. Victory!

Absolute genius. Diabolically simple yet subversively brilliant gaming.

Street Fighter .5: Pre-Industrial TURBO Edition!

Over a dozen battles *must* take place to amass enough of an insult vocabulary to have the slightest chance at besting the Sword Master. The process is so strangely fun, the act of empowering Guybrush against abuse is so fulfilling that winning over the Sword Master always leaves me feeling a little sad. The battles are ended (for now!) But once Guybrush stands atop the field, he’s heroic enough not to pick fights with those smaller and less dangerous than himself.

Which leads me to…


As with any truly great single-player experience, there’s something to be gained for later wisdom here. And to fully appreciate it, let’s head back to that muddy schoolyard puddle in March of ‘87.

There is little Shaun, unfamiliar with this new school, the target of a swollen doorknob of a bully. The new guy just wants to have a decent adventure, make a bit of an elementary school name for himself—why, he’s *NewGuy*brush. Heck, in the heavily German-descended town he just moved to, his two-syllable name is rather Threepwoodian in its sore-thumb-sticking strangeness.

Down he goes into the mud. Oof.

Oh, wait. Up he comes.

He’s saying something. And…are those other kids…kind of laughing at the bully?

It was a clever zinger that transformed an ugly memory into something different. Wit, even in the seconds following humiliation, led to a strange kind of win. Weird but true!

That same kid in the muddy jeans with the smear of fresh grime on his chin would soon be drawing laughs on a regular basis from other kids in class. Once, a well-timed joke about flatulence even drew a braying laugh from Brett.

For NewGuyBrush, it was wit that saved the day. Sure, he was a bit of a loser—who ISN’T sometimes, especially when we’re the new guy or gal and everything seems so out of reach? But as The Secret of Monkey Island made so clear, a willingness to put ourselves out there, armed with our best lines and a willingness to pick ourselves back up and defend ourselves with our best attempt at cleverness can incrementally nudge us through this tricky life.

Laughter, Ron Gilbert and Mr. Peepshould Threepwood remind us, is worth its weight in treasure, and make the whole adventure worth having.

Shaun Hayes

Shaun is a writer, English professor, host of the Whiparound podcast, and unrepentant grammar pedant.

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