The Funniest Moments In The Princess Bride Ranked

It's had no shortage of mainstream success, but even so, "The Princess Bride" may be the ultimate cult movie. Its tightrope-walk balance of cynical parody and sincere love of a good swashbuckling romance has ensured it remains just as popular today as it was when it first premiered in 1987. No wonder — it's got something for everybody. The nameless boy listening to his grandfather read the tale worries it's "a kissing book," but between all the romance, there's also plenty of action, fantastical settings, and comedy of all kinds, from the wittiest wordplay to the silliest pratfalls.

And if we judge a film's following by how widely it's quoted, "The Princess Bride" is hard to beat. The question is, how do we choose the funniest out of all those unforgettable quotes and other hilarious scenes? It wasn't easy to narrow it down, but like "twue wuv," we prevailed, and now we can count down the funniest moments in this very funny movie.

With "The Princess Bride," director Rob Reiner keeps the delicate balance of sincerity, parody, and camp by going back to the oldest trick in the book. It's one that dates back at least as far back as the silent swashbucklers "Bride" owes so much to and all the way up to the latest Marvel movie. That is, the characters know this is all in good fun just as much as the audience, and they react to events that would shock most of us with detached amusement.

One classic example is the improbably casual dialogue between Cary Elwes as Westley and Mandy Patinkin as Inigo Montoya after a cut rope leaves Westley stranded halfway up the Cliffs of Insanity. Westley asks Inigo to throw down the remaining length of rope so he can get to the top. Inigo responds, as if he were discussing a minor disagreement about the best Rolling Stones album, "I do not think you would accept my help since I am only waiting around to kill you." Westley's response is even more hilariously understated: "That does put a damper on our relationship." After some haggling, Westley finally takes the deal, and as promised, Inigo tries to kill him — though he seems more interested in having finally found a worthy fencing opponent than actually landing the fatal blow.

After Prince Humperdinck separates Westley and Buttercup once again, Buttercup has what's eventually revealed to be a nightmare about her eventual royal wedding. And it's here that Margery Mason, credited only as "the Ancient Booer," follows the old adage to "speak now or forever hold your piece." She speaks the heck out of it. The entire cast is having a ball trying to out-act each other, but Mason manages to top them all in around 30 seconds of screen time.

She breaks a relatively quiet scene by repeatedly shouting "boo!" out of nowhere before we even see her onscreen — and once we do, she's standing out in a crowd of much younger, better-dressed spectators. She makes a meal out of every one of those boos, and screenwriter William Goldman (adapting his own, even more meta book) gives her plenty of other choice, less monosyllabic lines. Some of her most colorful insults include, "Bow down to her if you want! The queen of filth! The queen of slime! The queen of puu-tresence! Boooooo!"

Fezzik is many viewers' favorite character, no doubt because André the Giant took a character who could have been a terrifying man-mountain and gave him a charmingly childlike personality beneath all the pounds of muscle.

For instance, just look at his role in the ending. He's vanished for most of the climax since it was a four-way grudge match with Westley vs. Humperdinck and Inigo Montoya vs. the Six-Fingered Man. Then Inigo hears Fezzik calling him and finds the giant beneath their window with a team of four horses. He explains that while the others were fighting, he discovered Humperdinck's stables and says gleefully, "There they were! Four white horses! And I thought, there are four of us, if we ever find the lady." 

And then he sees Buttercup and channels his inner child to give "hi, lady!" just the right note of endearing innocence. Fezzik may crack heads for a living, but you've still gotta love him.

His character may not survive long past the movie's first 30 minutes, but as the nefarious Vizzini, Wallace Shawn is easily a cast MVP. He gets a showcase as good as any Shakespeare monologue when Westley challenges him to "a battle of wits, to the death" over a poisoned cup of wine. Vizzini proceeds to prove his mental superiority by narrating his complicated and increasingly tenuous thought process for almost five minutes. Then he switches the goblets when our hero isn't looking and drinks from Westley's.

Westley wryly comments he's chosen the poisoned cup, which just confirms in Vizzini's mind that he's won, and he celebrates his supposed victory with the taunting only a blowhard like him can dish out, saying, "You fell victim to one of the classic blunders — the most famous of which is never get involved in a land war in Asia — but only slightly less well-known is this: Never go in against a Sicilian when death is on the line!" The reference to the Vietnam War in the middle of this medieval fantasy is already hilarious. But let's not sleep on Wallace Shawn expertly deploying his trademark high-pitched voice to make the line "never go against a Sicilian when death is on the line!" — barely a joke at all on paper — into a hilarious one.

As Miracle Max, Billy Crystal gets even less screen time than Wallace Shawn, but if anything, he makes an even bigger impression. After Fezzik and Montoya discover Westley near death from the six-fingered Count Rugen's (Christopher Guest) torture device — so horrible it's only called "the Machine" — they need a miracle, so they go to the miracle man. What they get is a bitter, cranky, old codger straight out of Crystal's Borscht Belt stand-up

He reluctantly agrees to help the motley crew of heroes and determines Westley is only "mostly dead," which he explains with impeccable fairy-tale logic "means slightly alive." This is good news, because, as Max explains, "With all dead, well, with all dead there's usually only one thing you can do." When Inigo pushes him to elaborate, he answers with one of the darkest bits of comedy in this lighthearted adventure: "Go through his pockets for loose change."

During "The Princess Bride," the heroes' relaxed attitude to their death-defying circumstances makes them more lovable, giving us the sense that they're in on the joke right along with us. The villains get in on the action too, but their flippancy only makes them more hateable and callous. 

For instance, after dropping Westley at Count Rugen's torture dungeon, Rugen invites Humperdinck to watch him at work — that work, again, being acts of unthinkable cruelty. Humperdinck politely declines, saying, "I've got my country's 500th anniversary to plan, my wedding to arrange, my wife to murder, and Guilder to frame for it; I'm swamped." Incongruity is a surefire way to get a laugh, and what could be more incongruous than describing an evil plot in the same flat tone as a shopping list? It doesn't hurt at all that screenwriter William Goldman makes sure to start the list off with ordinary royal duties that seem totally in keeping with Humperdinck's tone before dropping in the murder and war profiteering. After all, if there's anything better for comedy than incongruity, it's surprise.

We've covered a lot of classic joke types here, and few are more classic than the bait-and-switch. Play up a scene to go one way and then send it careening the opposite direction. For a perfect example, look no further than the moment Inigo finally encounters Count Rugen. 

After spending most of the movie (and his life) searching for the mysterious Six-Fingered Man so he can tell him, "My name is Inigo Montoya, you killed my father, prepare to die," the Spanish swordsman finally meets his mortal enemy in the halls of Humperdinck's palace. Count Rugen turns, draws his sword, assumes a fencing stance, and it seems like an epic battle is about to begin. And then he runs away like the dirty coward he is.

It's a great bit, and Christopher Guest sells the heck out of it, both the badass posturing for the bait and the extremely un-badass run when it's time for the switch. People always talk about actors and their egos, but Guest is obviously not above embarrassing himself, even if it means running exactly like a little kid.

True love doesn't strike Miracle Max as a good enough reason to bring Westley back from mostly dead to fully alive. But when he learns Inigo and Fezzik have given him an opportunity to get back at Humperdinck for throwing him out of the palace and into a hut in the woods, he's far more enthusiastic.

Once he gets Westley all fixed up, his wife Valerie (Carol Kane) joins him to send the former Dread Pirate Roberts on his way with a cheerful goodbye. Maybe a little too cheerful, given the circumstances. They call out, "Have fun stormin' the castle!" It's like they're parents sending their kids off to camp instead of sending soldiers off to war. The scene only gets funnier when the couple adds their more honest, cynical thoughts under their breath. "Think it'll work?" Valerie asks. "It'd take a miracle," Max replies before they get back to their sunshine-and-flowers act for the heroes' benefit.

The script may kill off Vizzini early on, but Wallace Shawn keeps us laughing right until the very end. That's also an accurate description of how he dies. Not realizing Westley has stayed two steps ahead of him by poisoning both goblets, Vizzini thinks he's outsmarted his opponent with the most childishly transparent "look over there" trick in cinematic history. He's not a gracious winner either. Once he's done gloating, he starts laughing and laughing until he's red in the face ... before he learns the hard way he didn't outsmart Westley and collapses mid-"ha."

What elevates this scene to the top spot isn't just the timing or delivery. It's also a great physical performance, as Shawn, without losing his cheerful expression, falls straight over in defiance of physics. Instead of making the more realistic choice to collapse forward onto the table or backward onto the ground, he falls sideways, disappearing from the frame like a reverse game of peek-a-boo. And since that's one of the first things every baby learns to laugh at, it's hard for even the most jaded adult not to react to Vizzini's sudden death.