32 Random Observations I Had About The Princess Bride After Having Watched It An Inconceivable Number Of Times

Westley and Buttercup facing each other in The Princess Bride
(Image credit: 20th Century Fox)

The first time I saw The Princess Bride, I was a kid, and though I watched it on VHS, it was -- I'm dating myself here -- still a fairly new movie at the time, as I recall. Obviously it was out long enough that it was available to rent, but it was also still new enough that I hadn't heard of it until then. Child-me had no idea that I was about to watch one of the best romantic comedies, and what would be one of my favorite movies of all time. This 1987 film -- based on a book by William Goldman --  would stay with me for decades. I've seen this movie many times since that first viewing, and this time around, I want to share my thoughts. 

This article is obviously full of spoilers, so read on with caution. I'm also mostly going chronologically, as I jotted down thoughts as the movie played...

Grandpa sitting with the book in The Princess Bride

(Image credit: 20th Century Fox)

I Think I Forgot This Takes Place Around The Holidays

If I'm thinking of the best Christmas movies, I'm going to be honest, The Princess Bride isn't one that would come to mind. It's possible that I never noticed this, but based on the decorations around the grandson's (Fred Savage) cluttered bedroom, including an angry looking home-made Santa on the closet door behind Grandpa (Peter Falk) -- and the lit up house across the street (seen briefly through the window), it appears this movie took place sometime around the holidays. Either I missed that, or I just forgot. 

Grandpa talking about the story in The Princess Bride

(Image credit: 20th Century Fox)

Grandpa Teases Most Of The Biggest Moments Right From The Start And It Somehow Doesn't Spoil The Story

It's clear pretty early on that the grandson is dubious about being read to as a gift. When he asks if the story has any sports in it, Grandpa responds by basically giving up some of the best things about the story. Of course, he's vague and it doesn't really reveal anything specific, but it's all right there in his pitch!

Vizzini talking in The Princess bride

(Image credit: 20th Century Fox)

It Took Several Other Great Wallace Shawn  Performances To Get Me To Think Of Him As Anyone Other Than Vizzini

This movie is my first distinct memory of Wallace Shawn in a role, and he plays Vizzini so inconceivably perfectly that I associated the actor with the overconfident and potentially murderous Princess Bride character for years. Shawn is undoubtedly great and funny in The Princess Bride, but Vizzini is also super mean and pretty unapologetic about his plans to kill Buttercup (Robin Wright). I'm glad to have movies like Toy Story (and its sequels), Clueless and -- the underappreciated and excellently cast '90s movie -- House Arrest to associate with the actor as well. 

Fezzik and Inigo talking on the ship in The Princess Bride

(Image credit: 20th Century Fox)

Can We Talk About The Way Inigo Immediately Cheers Up Fezzik By Getting Him To Rhyme? 

Right after Vizzini rants at Fezzik and threatens to fire him, Inigo immediately approaches Fezzik and prompts him to rhyme. This cheers Fezzik up immediately and it's the cutest moment. I love the "anybody want a peanut" line, but I also need to show some appreciation for Inigo for shifting the mood when he saw Fezzik being talked down to.

Buttercup surrounded by eels in the water in The Princess Bride

(Image credit: 20th Century Fox)

Oh, That's Right, The Princess Bride Is The Film That Made Me Terrified Of Eels

Before The Little Mermaid cast two eels as spying minions for Ursula, there were the shrieking eels, which encircle Buttercup in The Princess Bride, and one nearly bites her with its giant teeth. These scary swimmers were among the fictional beings that terrified me as a kid (see also the Skeksis in The Dark Crystal and those scary dogs in Willow). 

Indigo chatting with the Man in Black in The Princess Bride

(Image credit: 20th Century Fox)

I Love That Inigo Gives The Man In Black A Few Minutes To Catch His Breath Before They Duel 

Westley (Cary Elwes) -- as the Man in Black at this point in the movie --  just climbed a cliff with just a rope and his two hands. Considering Inigo (Mandy Patinkin) was carried up by Fezzik (Andre the Giant), it's truly decent of him to give Westley a few minutes to catch his breath before they fight. And turns out, using that time to talk about his quest for vengeance might have helped warm Westley to him. Neither of them seemed to be fully out for blood in this fight, but at the end of the impressive duel, Westley acknowledges Inigo's artistic abilities before knocking him out, rather than killing him. 

Westley and Inigo fencing in The Princess Bride

(Image credit: 20th Century Fox)

"I Am Not Left-Handed Either" - The Theatrics! 

There's a playfulness to the fencing duel between Inigo and Westley when they face off, but it doesn't get truly theatrical until Inigo reveals he's not left-handed, to which Westley responds with a similar confession. It's a perfect moment in a movie that has no shortage of them. 

Fezzik fighting with the Man in Black in The Princess Bride

(Image credit: 20th Century Fox)

All Of The Great Fighting Banter!

The fact that Fezzik and Westley can keep up with each other's banter throughout their brief fight is just one more thing to appreciate about their scene. But it also shows a lot about Fezzik's character that he insists on fighting in a sportsmanlike manner -- and without his opponent being embarrassed when he dies. Fortunately, Westley doesn't. 

Vizzini holding Buttercup at knifepoint in The Princess Bride

(Image credit: 20th Century Fox)

Did Vizzini Really Just Call Plato, Aristotle, And Socrates Morons?!

Vizzini is the worst for a lot of reasons. Well, maybe he's tied for the worst with the sadistic Count Rugen (Christopher Guest), but he's a whole other villainous story. For Vizzini, he's already unlikable by the point at which he has a knife to Buttercup's throat, but then he shows off his massive ego by insulting some of the celebrated philosophers of the past. 

Vizzini laughing in The Princess Bride

(Image credit: 20th Century Fox)

It's Morbid, I Know, But I Still Laugh When Vizzini Falls Over Dead Mid-Laughter

He has only himself to blame -- and not just for being tricked into drinking the poison. Technically, Westley's challenge against Vizzini was a bit of a trick since there was poison in both glasses and he was immune, but it was Vizzini who switched the goblets after distracting Westley, presumably for no other reason than so he could get the last laugh when Westley thought he drank from the other cup. Turns out, laughing was the last thing Vizzini would get to do.

Buttercup telling off Westley in The Princess Bride

(Image credit: 20th Century Fox)

Buttercup Is Fearless. 

This was just something I wrote down right around the part where Buttercup yelled at the Man in Black -- not knowing he's Westley quite yet -- and pushed him down the hill. Even when she's being held against her will by various captors, she never backs down from anyone. 

Westley looking at Buttercup as they lay on the grass

(Image credit: 20th Century Fox)

I Love How Quickly Buttercup And Westley Put All Anger Behind Them The Minute She Knows He's Alive

In a nutshell, sorry about pushing you down the hill, Westley -- thought you were just a pirate! Buttercup is quick to get over her surprise at realizing that the Dread Pirate Roberts is actually her sweet Westley and he's not at all bothered by her recent outrage. 

Westley and Buttercup walking through the Fire Swamp in the Princess Bride

(Image credit: 20th Century Fox)

The Fire Swamp Still Scares The Life Out Of Me

This might be stating the obvious but the Fire Swamp is a nightmare. Dark, scary and full of terrifying things like lightning sand, flame spurts and giant rat monsters called Rodents Of Unusual Size (R.O.U.S.es). 

Westley holding Buttercup in The Princess Bride

(Image credit: 20th Century Fox)

The Fact That We Get A Catch-Up On What's Been Going On With Westley As Flames Spurt Up From The Ground Is Kind Of Fun...

I actually appreciate how the movie uses this otherwise scary sequence to fill us in on what Westley's been up to for the five years (!!!) he's been away from Buttercup. Just learning how to be a pirate and what not. But at least it explains how he's so good at fighting and fencing.

Westley and Buttercup standing near an ROUS in The Princess Bride

(Image credit: 20th Century Fox)

Westley Wrestling With The R.O.U.S. Is Still Horrifying

There's something about the way Westley screams when the giant rodent bites his shoulder that still gives me chills. And then there's all the tension that builds up as he wrestles with the R.O.U.S., at one point holding its mouth open right in front of his face.

Count Tyrone Rugen smiling in The Princess Bride

(Image credit: 20th Century Fox)

The Shock I Felt The First Time I Saw The Reveal That Count Tyrone Rugen Is The Six-Fingered Man

I don't always remember the exact feeling of surprise I experienced when seeing a big reveal in a movie for the first time, but in the case of the sight of Rugen's gloved hand and the reveal that he's the six-fingered man, I can still remember making that connection to Inigo's story with a gasp when watching the movie for the first time. It's such a great moment.

The Machine in The Princess Bride

(Image credit: 20th Century Fox)

Right, The Horrors Don't End With The Fire Swamp. There's A Torture Machine

At this point in The Princess Bride, we already know that Count Tyrone Rugen is the six-fingered man and has a history of doing terrible things like cutting the face of an 11-year-old boy after killing his father, but the movie paints an even worse picture of this character when we're introduced to The Machine, a torture device created by Rugen that's used to suck years off of its victim's life. 

Fezzik smiling down at Inigo in The Princess Bride

(Image credit: 20th Century Fox)

Fezzik And Inigo Are Kind Of An Unsung Bromance

The look on Inigo's face when he realizes it's Fezzik who's with him where he's been waiting for Vizzini, to the sight of Fezzik taking care of Inigo (which apparently includes dunking his head into water barrels) is just one example of what a great bromance these two have in this movie. I don't think we talk about that enough, and I like to think that this movie is just the start of their adventures together. 

Inigo asking for guidance in The Princess Bride

(Image credit: 20th Century Fox)

Watching The Magical Moment Of Inigo's Sword Finding The Pit Of Despair

If there's more than one miracle in The Princess Bride, this has to be one of them. Just when it seems like Inigo and Fezzik's luck has run out, Inigo begs for guidance from his father in the hopes of discovering the entrance to the Pit of Despair where Westley is being kept prisoner. It's just one of many great scenes involving Inigo. 

Valerie and Miracle Max in The Princess Bride

(Image credit: 20th Century Fox)

Carol Kane And Billy Crystal Are Treasures 

As great as Billy Crystal is in his role as the bitter but energetic Miracle Max, Carol Kane always gets me laughing when she enters the scene by fiercely calling her husband a liar. These two are incredible. 

Fezzik holding westley's head in The Princess Bride

(Image credit: 20th Century Fox)

The Physical Humor On Display With Post-Miracle Westley Is Fantastic

After being revived from being mostly dead, Westley is too weak to move at first, which leads to a series of great moments involving him unable to lift his head and having to be physically manipulated and posed by Fezzik. The way it all fits into the conversation Westley, Fezzik and Inigo are having about how to storm the castle is so great. 

Fezzik gesturing to Inigo to go through the door in The Princess Bride

(Image credit: 20th Century Fox)

Fezzik Never Fails To Come Through

Fezzik is probably the most reliable of anyone in this movie, right down to the moment where he temporarily leaves Westley in the arms of a knight's armor in order to break down a door so Inigo can pursue Count Rugen. 

Inigo falling down in The Princess Bride

(Image credit: 20th Century Fox)

The Disappointment On Inigo's Face After The Knife Hits Him Is Heartbreaking

My heart! The sight of Inigo as he realizes he might have just failed in his quest to exact vengeance on his father's killer crushes me. The look on his face is just one of countless reasons why Mandy Patinkin is truly brilliant in this role. 

Inigo staring down Rugen in The Princess Bride

(Image credit: 20th Century Fox)

The Satisfaction When Inigo Finds The Strength To Exact His Revenge

Though he's bleeding and exhausted, Inigo proves he's not one to give up and not only manages to protect himself against Rugen, but he quickly turns the tables on the Count and gets him backed into a corner, begging for his life (which Inigo declines to spare). Hello...!

Westley staring down Humperdinck in The Princess Bride

(Image credit: 20th Century Fox)

Westley Uses His Strength, His Sword And His Brains To Take Down Humperdinck

Throughout the movie, we see Westley proving his strength, agility and quick wit. All three prove to be pivotal when he faces off with Humperdinck, threatening to completely ruin him (but leave him alive so he can live out his ruined life) until Humperdinck surrenders. Humperdinck might've claimed afterward that he knew Westley was bluffing, but let's face it, he didn't. 

Westley and Buttercup about to kiss in The Princess Bride

(Image credit: 20th Century Fox)

We Finally Get To See An Uninterrupted Kissing Scene

I love how picturesque all of Westley and Buttercup's kissing moments are. Their final one, right before they leave the castle, is no exception. And this time, the grandson doesn't cut his grandfather off when the two characters are about to lock lips. In fact, when Grandpa is about to skip that part, the grandson says he's ok with it. Awww! 

The Grandpa saying "As you wish" as he leaves in The Princess Bride

(Image credit: 20th century Fox)

The Movie Ends With A Great Smile, And A Reminder Of How Wonderful It Can Be To Pass A Story Down To Another Generation

There are some great smiles in this movie, and one of the best is the one Grandpa gives to his grandson when he suggests he come back and read the story to him again. As you wish! 

Fezzik holding Buttercup and smiling in The Princess Bride

(Image credit: 20th Century Fox)

Let's Pause For A Minute And Celebrate The Looks On Fezzik And Buttercup's Faces When He Catches Her

There's a magical moment near the end when Buttercup drops from the window and flutters down into the waiting arms of Fezzik. But it's the smiles on their faces after he catches her that get me. So sweet!

Grandpa reading from the book in The Princess Bride

(Image credit: 20th Century Fox)

Credit To Grandpa For Spoiling The Part About Humperdinck's Fate And Still Somehow Not Ruining The Ending

Grandpa may have made references to key moments in the story before he even started reading the book to his grandson, but when the frustrated boy demands to know who kills Humperdinck, Grandpa flat-out tells him that Humperdinck lives -- and he's not even lying! As much of a spoiler as it seems to be, we still don't know how it all plays out at that point, so it's ok. Kind of great, in fact, as we're left to wonder if maybe things go wrong. 

Buttercup looking at Humperdinck in The Princess Bride

(Image credit: 20th Century Fox)

Credit To Buttercup For Never Doubting That Westley Would Come For Her (Until She Thinks He Didn't, And Even Then, She's In Disbelief)

I love the way Buttercup never wavers in her confidence that Westley will show up for her. At least, not until the rushed wedding ceremony wraps up and he doesn't show, and even that she seemed almost dazed in her disappointment and confusion. Because of course he'd show up... 

Westley smiling at Buttercup in The Princess Bride

(Image credit: 20th Century Fox)

Credit To Westley For Knowing Without A Doubt That Buttercup Would Never Have Said "I Do"

Buttercup showed her confidence that Westley would return numerous times throughout the second half of the movie. Westley seems to repay that unwavering loyalty when he knows without even having been there that there's no way Buttercup said "I do" to Humperdinck, so they couldn't possibly be married. Brilliant. 

Inigo considering a career change in The Princess Bride

(Image credit: 20th Century Fox)

Credit To Fezzik And Inigo For Never Giving Up, For Supporting Each Other, And In Inigo's Case, Considering A New Career Post-Vengeance

It's happy endings for all of the good guys in The Princess Bride, and that includes Fezzik -- who does one more awesome good deed by finding four horses to carry them off -- and Inigo, who pauses to consider the possibility of following up his recent retirement from the revenge business with a career change as the next Dread Pirate Roberts. Seems like a good option for a swordsman such as him, right? 

And those are just some of the thoughts I had while revisiting one of the best '80s movies. Those with a Disney+ subscription can find the movie streaming there. 

Kelly West
Assistant Managing Editor

Kelly joined CinemaBlend as a freelance TV news writer in 2006 and went on to serve as the site’s TV Editor before moving over to other roles on the site. At present, she’s an Assistant Managing Editor who spends much of her time brainstorming and editing feature content on the site. She an expert in all things Harry Potter, books from a variety of genres (sci-fi, mystery, horror, YA, drama, romance -- anything with a great story and interesting characters.), watching Big Brother, frequently rewatching The Office, listening to Taylor Swift, and playing The Sims.