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.

One of the greatest assets of "The Princess Bride" is its deep bench of acting talent. But as we celebrate the flashy, campy performances of Cary Elwes, Mandy Patinkin, Wallace Shawn, and the rest, we can't afford to ignore the subtler charms of André the Giant as Fezzik. Depending on whether you consider wrestling a form of acting, he was one of the least experienced stars on the set, but that plays to his benefit because his flat line readings give Fezzik a deadpan sense of humor that makes him a highlight.

Take, for instance, his first meeting with Westley, who isn't too happy with his odds against Fezzik in hand-to-hand combat. Fezzik tries to reassure him, saying, "It's not my fault I'm the biggest and the strongest," and then, with a mischievous smile, "I don't even exercise." That smile might have been André enjoying a private joke — like Fezzik, Men's Health reports, he didn't see any need to bulk up any further. Thanks to a pituitary disorder called acromegaly, he was simply born big. Jason Hehir, director of the documentary "André the Giant," says, "What steroid abusers and now HGH users are going for ... was actually the disorder that André had."

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.

Westley and Buttercup (Robin Wright) finally reunite after years of Westley sailing the sea as the Dread Pirate Roberts and Buttercup mourning his apparent death. But they don't have much time to catch up since they're the run from her new fiance, Prince Humperdinck (Chris Sarandon), and the full might of his Florinese army. 

Westley plans a daring escape through terrain where not even the army will follow — the ominously (and, it turns out, accurately) named Fire Swamp. Buttercup is understandably concerned, warning Westley, "We'll never survive!" Westley's response is a perfect example of his cheerful bravado and a feat of "Alice in Wonderland"-esque illogical logic: "Nonsense. You're only saying that because no one ever has."

Fortunately, Westley is right, possibly because he knows as well as the viewers that he's the hero, and the hero can't die. They survive, but just barely, once Westley convinces Buttercup to follow him. He has far less luck convincing her that the Fire Swamp is "not that bad," though.

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!"

After defeating Inigo Montoya, Westley finds another opponent standing between him and Buttercup when a boulder nearly splits his head open. Fezzik appears to say that was just a warning shot, and if he'd wanted to, he really could have split Westley's head open. Fortunately, after a conversation with his boss, Vizzini (Wallace Shawn), that we'll be discussing in more detail soon, the giant has decided he's more interested in a fair fight. "Skill against skill alone." 

Westley, as always, is fully aware of the absurdity of his situation. "You mean you'll put down your rock, and I'll put down my sword, and we'll try and kill each other like civilized people?" Fezzik, missing the joke, happily agrees. His idea of a fair, civilized fight isn't just uncivilized, it's unfair since the giant easily has a couple hundred pounds on his opponent. But Westley succeeds against the odds, and his adventure continues.

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.

The main events of "The Princess Bride" come inside the framing device of "Wonder Years" star Fred Savage sick in bed and his grandfather — played by Columbo himself, Peter Falk — bringing over his favorite childhood book to make the kid's bedridden day more bearable. They reappear throughout the movie to offer running sarcastic banter, Statler-and-Waldorf-style.

Most of the sarcasm comes from the boy, who's annoyed to be listening to a "kissing book," but the grandfather gets the biggest zinger after Buttercup's wedding nightmare. The boy interrupts the story in disbelief at the beginning of the scene, and then when the grandfather reveals it was all a dream, the boy proudly interjects, "See, didn't I tell you she'd never marry that rotten Humperdinck?" 

The affectionate grandfather breaks character for a brief, hilarious moment, responding, "Yes, you're very smart. Shut up." And then he launches back into the story so quickly it takes a second to register his unexpected casual cruelty. And like the best jokes, once it does register, it's impossible not to start laughing.

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.

Fezzik may be mixed up with a dirty crook who's willing to kidnap and murder a helpless young woman to cause even more death in a war between Florin and Guilder, but we see his true colors early on when Vizzini realizes Westley has defeated Inigo. 

Frustrated, the mastermind demands that Fezzik "finish him your way!" At first, the giant's flattered to get to choose his mode of combat, but then he realizes he has no idea what Vizzini means. "Which is my way?" he asks, and Vizzini — who's already been running about a 10 in exasperation throughout the movie — explodes up to 11, ranting that Fezzik needs to take big, heavy rock, hide behind a boulder, "and the minute his head is in view, hit him with the rock!" 

Throughout it all, Fezzik remains just as calm as Vizzini is agitated, and he can only shake his head and say, "My way's not very sportsmanlike," with all the dryness of a discussion about yardwork instead of bloody murder.

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."

Being, in Fezzik's words, "mostly dead all day," Westley is understandably confused when he wakes up at the castle gates with two dudes he last saw trying to kill him. "Let me explain," Inigo says. Then he pauses, and you can see the wheels turning in his head as he tries to figure out where to start ... and finally gives up. "No, there is too much. Let me sum up."

This line hasn't been quoted as endlessly as some of the others on this list, but it's applicable to so many situations that we've all had a chance to use it at least once. It could be a long day at work, a friend walking in on an episode out of the middle of the eighth season of your favorite TV show, or a meme that would take a full course in internetology to explain to your less web-savvy friends. In these moments, we all are Inigo.

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 can analyze these moments all we want, but some of them are brilliant precisely because of their childish simplicity. And as anyone stuck with their younger siblings for too long knows, plenty of children have come up with the rhyming game Fezzik and Inigo play on their voyage to Guilder. After both characters endure a round of verbal abuse from Vizzini for daring to point out his evil scheme is kind of, well, evil, Inigo starts the game to lift Fezzik's spirits. Needless to say, Vizzini does not care for all the rhyming.

Nobody does impotent exasperation quite like the tiny Wallace Shawn, and it's almost as fun to watch André and Patinkin needling him as it must have been for their characters. Finally, Vizzini puts his foot down, hollering, "No more rhymes, and I mean it!" And like any child getting told off by an older brother, Fezzik, unfazed, can't resist getting one last kick in, saying, "Anybody want a peanut?" Vizzini's scream echoes across the water, and since it's dark by the time of the next scene, for all we know, Inigo and Fezzik kept it up well into the night.

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.

As Westley and friends assault the castle, Humperdinck has already begun his wedding to Buttercup, and he has murder planned in lieu of a honeymoon. Officiating the ceremony is British comedy legend Peter Cook, credited only as "the Impressive Clergyman." When we first see him, he certainly looks the part — old, venerable, and imposing. And then he opens his mouth. 

Cook gives his Impressive Clergyman the high-pitched voice of a toddler, including some trouble with his Rs and Ls. "Mawwiage!" he says, "is what bwings us togevvah today!" The Impressive Clergyman provides a ticking clock to the heroes' invasion of the palace as the film cuts back and forth between the good guys fighting their way inside and the ceremony, and it doesn't help at all that Humperdinck keeps hurrying the clergyman up. But director Rob Reiner doesn't let that tension spoil the silliness, so every time we return to the wedding, the Clergyman is saying something like, "Wuv, twoo wuv wiww fowwow you foweva," as Cook makes a meal of the vowel sounds in "twoooo wuuuvvv."

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.

Now we come to the "Princess Bride" line almost everybody knows. Vizzini is fond of describing every possibility that might muck up his plans as "inconceivable" — which is already a good candidate for this list just for the slight lisp Wallace Shawn adds and the way his voice squeaks on the middle syllable. Of course, every one of those things turns not to just be conceivable but possible. And they're not just possible, they actually happen. Finally, Inigo confronts his boss about his continually inaccurate assessment of their situation, saying, "You keep using that word. I don't think it means what you think it means."

It's the most frequently applied and readily applicable line in the whole screenplay. At some point in all our lives, we've all had to deal with someone possessing delusions of eloquence who's misusing words, misunderstanding concepts, and generally mangling the language. Online arguments would be inconceivable without it!

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.