Rob Reiner’s The Princess Bride is a cinematic masterpiece. Based upon a book of the same name, the story has everything you could possibly want in a fantasy movie: action, adventure, romance, comedy, and a number of kooky characters are all present in the legendary tale. Thirty years after its release this movie still holds a 97% on Rotten Tomatoes and is often called one of the greatest movies ever made. Perhaps the most endearing part of The Princess Bride is its cast; who else could play such pop culture icons as the Dread Pirate Roberts or Inigo Montoya? Well, we’re going to try and find out!
Before we begin, we’d like to remind you that this article is purely for fun. We understand just how beloved The Princess Bride is and we wouldn’t want anyone to even float around the idea of a remake, much less move forward with one. But in this dark timeline where William Goldman’s novel was getting a 2017 adaptation, here is a list of actors we think would be chosen to play the characters.
Without further ado, we pose the question: What If The Princess Bride Was Cast Today?
17. The Ancient Booer – Kristin Wiig
Though you probably just know her as the crazy lady in Princess Buttercup’s nightmare, the Ancient Booer plays a significant role in the progress of the story. She is the one who reaffirms that if the princess marries Prince Humperdinck, she will have thrown away her chance at true love. Her iconic lines involve pointing out how she treated her true love like garbage and calling Buttercup the “Queen of Slime, the Queen of Filth, the Queen of Putrescence!”
SNL veteran Kristen Wiig is just about the only choice for this role. During her time as a cast member of the hit late-night sketch show, Wiig played a wide range of crazy and over-the-top characters such as Aunt Linda, Gilly, and Dooneese Maharelle (aka the baby hands girl).
Even within her film career Wiig has shown her comedic range, from the bizarre character she played in Anchorman 2 to the more subdued but equally hilarious character she played in Bridesmaids. Though her role would be little more than cameo, we just know that Wiig would make the Ancient Booer as memorable as she was in the original movie.
16. Yellin – Kristofer Hivju
Yes, this character does have a name! Yellin is the Chief Enforcer of the Kingdom of Florin. Though he is a loyal servant to his King, he is not exactly the brightest. When Prince Humperdinck informs him that Florin’s enemies in Guilder are planning to assassinate Princess Buttercup, Yellin does the villain’s bidding without a second thought. On Buttercup and the Prince’s wedding day, he and his men storm the Forbidden Forest and round up anyone who they deem a threat to the royal couple. During the ceremony Yellin and his men are scared off by the trickery of Wesley, Inigo, and Fezzik.
Better known as Tormund Giantsbane in Game of Thrones, Kristofer Hivju would make a perfect Yellin. The actor gives off an aura of badassery at all times, with his piercing eyes and grizzly-man look. Underneath his appearance, the actor has shown he can do comedy; Tormund has become a fan favorite in GoT mostly because of his brutally honest and sarcastic attitude. On top of this, imagine the hilarity of the contrast when the three heroes storm the castle: You’d have Hivju, the epitome of toughness, reduced to a bumbling coward and deliver the iconic “Oh, you mean this gate key?”
15. The Queen – Glenn Close
Speaking of characters whose names you didn’t know… here is one who legitimately doesn’t have a name! The Queen is the co-ruler of Florin and the mother of Prince Humperdinck. Much like her husband, the Queen doesn’t know about her son’s dark side. or the evil plot he has planned once he ascends to the throne. The Queen in The Princess Bride is about as minor of a role as you can get; she only appears in a single scene and only has one line of dialogue in the entire movie.
However, a trend in movies today is to have a popular actor show up as a cameo for a scene or two; this allows the filmmakers to generate buzz with an A-list cameo whilst only having to pay the actor for a few days of work. In this case, the Queen would be played by six-time Academy Award nominated actress Glenn Close. Close is an actress who can bring a hint of charm to any role she plays, as evidenced by her role in the Guardians of the Galaxy franchise. Perhaps her inclusion in The Princess Bride would turn what was basically a throwaway character into something much more special.
14. The King – Liam Neeson
Although he has a larger role in the film than his wife, the King of Florin is also a bit part that is played up for laughs. The King has grown senile, resulting in his son taking over the duties of the ruler without actually holding the title. He appears alongside Humperdinck in most of the scenes involving the wedding (or dreams about it), smiling unknowingly at the sinister situation at hand.
After the wedding is done, he and his wife escort Buttercup away, where she gives him a kiss and says that she’ll miss him once she kills herself. The senile old King simply responds with “wouldn’t that be nice?” before giddily running off and exclaiming that the Princess kissed him.
If you take just one look at the King of Florin you can see a huge resemblance to Liam Neeson. The Taken and Love Actually actor would be an excellent yin to Glenn Close’s yang. Neeson is also finally at the age where he can play a convincing “older” character; despite his great looks, the actor is in his 60s!
Not to mention, he’s funny as hell! You wouldn’t know it from watching most of his films, but Liam Neeson has a major funnybone. Don’t believe us? Check out his guest appearance on Life’s Too Short, where he tries to do improv comedy with Ricky Gervais to some hilariously dry results.
13. Miracle Max – Steve Carell
The loud-mouthed, snobby medicine man Miracle Max is one of the most memorable characters in The Princess Bride. After Wesley’s unexpected death from Count Rugen’s torture device, Fezzik and Inigo bring him to Miracle Max in the hope that he can be brought back. Max points out that Wesley isn’t dead (just “mostly dead“) but still refuses to revive him without the proper payment. However, Max is eventually persuaded by his wife and his hatred for Humperdinck to save our hero. Miracle Max is played brilliantly by Billy Crystal in the original film, meaning that it would take someone with top-notch comedy chops to take over the part.
Enter Steve Carell. If you need an actor to play an over the top goofball, there are few better choices than this guy. He played the lovable and awkward loser Michael Scott for seven seasons on The Office, the good-hearted villain Gru in the Despicable Me Series, the bumbling Maxwell Smart in Get Smart, and (of course) he was the titular character in The 40-Year Old Virgin. Steve Carell’s history of playing selfish, sarcastic characters who actually have a heart of gold makes him choice #1 for Miracle Max.
12. Valerie – Amy Poehler
A big part of what makes Miracle Max’s scene so great is the bickering between Max and his wife, Valerie. Max refuses to save Wesley after he finds out what he’s really fighting for: True love. Just as the medicine man is about to kick the three protagonists out, Valerie comes around the corner screaming at Max about how he’s a liar and a coward, torturing him with the name “Humperdinck” and exclaiming that he’s letting true love go to waste. The chemistry between Crystal and Carol Kane was fantastic, meaning that this version of Valerie has to be someone who can hold her own against the talents of Steve Carell.
Amy Poehler has done that and then some! The SNL alum has been one of the show’s biggest success stories since her departure in 2008. She’s created and starred in Parks & Recreation and starred in many hit movies. Whenever you see the credits say “Written by” or “Created by” Amy Poehler, you know you’re going to be in for a treat.
As Leslie Knope in Parks & Recreation, the actress basically played Valerie (minus the accent). Her character was full of energy and gusto, and she was never afraid to say what was on her mind or do the right thing, even if her actions resulted in disaster. Picturing Carell and Poehler going back and forth as Max and Valerie is guaranteed to make you smile.
11. The Impressive Clergyman – Thomas Lennon
“Mawagge… mawagge is wot bwings us togethar, today… and love, twue love, will follow you forevar and evar.” He may only get less than two minutes of screen time but the Impressive Clergyman gave us a gut-busting scene and a quote that will live on with us “forevar.”
As his famous quote suggests, the Clergyman officiates the marriage ceremony of Prince Humperdinck and Buttercup as Wesley, Montoya, and Fezzik try to get past the royal guards to save the princess. Spectators at the ceremony can hear the chaos in the background as the Clergyman stumbles through the proceedings and Humperdinck gets more and more uneasy.
It takes a special type of actor to play this kind of character completely straight. Despite his funny way of speaking, the Clergyman is about as serious as can be. Beloved character actor Thomas Lennon is one of the few that we could see pulling this off.
Currently Lennon can be seen in the CBS show The Odd Couple, where he plays Felix, the neat and proper one of the duo. He also plays recurring characters on The Santa Clarita Diet, Bob’s Burgers, Dawn of the Croods, and numerous other TV shows. Most of his roles see him as a figure of authority who acts as the butt of the joke. Who better to play our Clergyman (or should we say “Cwergyman”)?
10. The Albino – Kyle Gass
We’re just going to say it: The Albino is freaking disgusting. Just look at him; he’s got frizzy white hair that’s just a tone darker than his own skin. He has a bunch of gross sores on his face, and speaks with a Smeagol-like voice until his bouts of hacking give him back his normal one. We really hope that’s a sore around his lips and not some sort of bile. The Albino works in Count Rugen’s torture chamber, The Pit of Despair. After Rugen returns to Humperdinck’s side, the Albino is left to torture Wesley with his dastardly machine.
Kyle Gass, of Tenacious D fame, would be the Albino in our story. Nobody doubts that Gass can play a weird and scummy character; that’s literally the version of himself he plays in his Tenacious D albums and movies all the time! Also, we know he can rock the long hair! The actor dons a hilariously bad wig in his band’s film Tenacious D in The Pick of Destiny to great comedic effect.
9. Count Rugen – Jesse Eisenberg
Tyrone Rugen, the pompous and sadistic count on Humperdinck’s court, is the baddie that we all love to hate. Obsessed with the study of pain, he tortures Wesley with a machine that literally takes years off of his life. Even as the hero screams in pain, Rugen simply smirks. Then there’s the fact that the Count is the six-fingered man who killed Inigo Montoya’s father and left Montoya with a scar across his face as a child. Rugen gives off this sly air of evil with every word that comes out of his mouth.
Jesse Eisenberg has made a career out of playing clever, cocky characters. Though he started out as a poor-man’s Michael Cera, the actor broke away from the stereotype with his roles in Now You See Me and The Social Network.
However, he never really played a villain until 2016’s Batman v. Superman: Dawn of Justice. The results were… polarizing, to say the least. Eisenberg’s Lex Luthor gave off a much more cocky and spoiled-brat vibe than fans were used to with the character. But it’s this kind of acting prowess that makes him a good fit for Count Rugen. Picturing any of his the Count’s lines being spoken by Eisenberg adds a whole new layer to the character.
8. Prince Humperdinck – Miles Teller
Speaking of characters that we love to hate… we’ve finally come to the much discussed antagonist of The Princess Bride, Prince Humperdinck. This guy just oozes arrogance; he fully controls the affairs of his senile father, essentially making him a King without a title. To solve this issue he wants to marry Buttercup, have her killed, blame Florin’s rival country for the assassination, and then go to war. What a D-bag. If that doesn’t make you hate him enough, he also has Wesley captured and tortured (and eventually killed) when he realizes that he and Buttercup share true love. For Humperdinck, we would need someone who can play an evil, arrogant jerk with a punchable face.
Don’t get the wrong idea here; Miles Teller is a great actor. But there’s something about him that rubs people the wrong way. Maybe it’s the fact that he was the lead in the godawful Fan4stic movie or that he auditioned for Han Solo without even knowing anything about the character. Or maybe it was just the fact that Teller played this kind of a character once already in the Divergent series. Let’s not forget to mention that the actor absolutely looks the part; he’s got the curly black hair, the pursed lips, and the sunken judgemental eyes that are all a major part of Humperdinck’s appearance.
7. Vizzini – Will Arnett
You all remember Vizzini (even if you don’t remember his name). Played by Wallace Shawn, the overconfident assassin leads Fezzik and Montoya in a plot to murder Princess Buttercup and blame Florin’s rival nation. The group captures the princess and are pursued by the Dread Pirate Roberts, and each of the henchmen are defeated before the pirate chooses to match wits with Vizzini. This character is known for his unique voice and his repeated use of the phrase “Inconceivable!”
It may be hard to picture besides Wallace Shawn in this role (what is Vizzini without his iconic voice?!), but we think that Will Arnett could pull it off. We just about left this character with the original actor. Then we got to thinking about Arnett, as G.O.B. Bluth, doing the poison scene. And it was hilarious.
Much like Jesse Eisenberg, Will Arnett has made his career out of playing overconfident and egotistical characters. However most of Arnett’s characters (LEGO Batman, G.O.B. Bluth, and BoJack Horseman to name a few) are hilariously incompetent, making him the only choice to take on this iconic role.
6. Fezzik – Dwayne “The Rock” Johnson
Fezzik is the incarnation of the “Gentle Giant” trope. On the outside, he’s an ugly brute that can crush bones with a flick of his wrist. On the inside, however, Fezzik is a big softie who is much more intelligent than he appears. This lovable big guy was the iconic role of wrestling phenom Andre the Giant, who sadly passed away before his star fully rose. True to the trope, Fezzik acts as the muscle of the group but also offers great wisdom when they’re are stuck in a sour situation.
Which makes Dwayne “The Rock” Johnson perfect for Fezzik! Despite being one of the more popular action stars today the Rock is often reduced to the role of the hulking CIA agent or bodyguard that accompanies the rest of the cast as they go into perilous situations. Johnson isn’t even close to being as large as Andre the Giant was. But then again, who is?
What the Rock lacks in the drama category he makes up for in his comedic talents; not only is Johnson funny, he has also made for some of the most hilarious unscripted scenes in recent memory. Casting the Rock as Fezzik would keep in the tradition of using WWE superstars, to boot!
5. Inigo Montoya – Diego Luna
Say it with us now! “My name is Inigo Montoya. You killed my father. Prepare to die.” Montoya’s battle cry is the most popular line of the film and has resonated throughout pop culture. There’s little question as to why the character is so popular; Inigo Montoya is a charismatic man with the spirit of a fighter and a tragic motivation. The audience gets so swept up in the character’s quest for the six-fingered man that when the confrontation finally occurs, we’re totally immerged in the character’s emotions.
Seriously, who doesn’t get emotional when Montoya declares, “I want my father back, you son of a bitch!” before killing the man he had pursued for decades? Mandy Patinkin brilliantly portrays the swordsman, and it’s difficult to picture anyone else in this role. However, we think that Diego Luna might just be able to pull it off.
Luna is still a relative newcomer to the Hollywood big leagues. Though he has been an actor, producer, and director for years, his star has recently grown with his role in Rogue One. Luna’s performance in the Star Wars flick showcases everything you’d want from an actor playing Inigo. He was a scoundrel who refused to play by the rules whilst simultaneously being charming and somewhat heartfelt.
4. Wesley/Dread Pirate Roberts- Freddie Stroma
Now we move on to the main characters of our story! The bond Wesley and Buttercup shared is a true love that can never be taken away. However, when Wesley’s ship is attacked by the Dread Pirate Roberts and her lover is presumed dead, Buttercup is forced to move on. Wesley returns years later to save his true love from the clutches of Vizzini after taking up the alias of the Dread Pirate Roberts. Cary Elwes makes it impossible to hate this character; his acting just puts on layers upon layers of charm and the actor’s comedic timing is incredible.
In the words of Will Ferrell’s character in Zoolander, Freddie Stroma is “so hot right now.” What isn’t this guy in nowadays? The English-born model turned some heads when he jumped into the world of acting, taking bit parts in the Harry Potter and Game of Thrones series. He finally hit it big in 2015 with his role on Lifetime’s original series unREAL, where he played a rich playboy taking part in a Bachelor-like reality series. He followed this performance up with a major role in 13 Hours and is set to star in ABC’s Time After Time starting this year.
There’s no denying that Stroma looks the part! He’s young, blond, and has the chiseled features that the character is known for. If you’ve every seen any of his TV shows you’ll notice that Stroma can do comedy, as well. But Wesley is just one half of the iconic duo…
3. Princess Buttercup – Constance Wu
Princess Buttercup is the real star of the show. Despite being overshadowed at times, The Princess Bride is her story at its core. Buttercup is the one who is kidnapped by Vizzini. She is the one at the center of Humperdinck’s plot to start a war with Florin’s rivals. She’s ultimately the one who ties up the villain and leaves him to his embarrassment. Despite her constant need to be rescued, Buttercup is portrayed as a headstrong and independent woman. The character was Robin Wright’s first real movie role and helped to springboard her career into what it is today.
We know that we’ve been harking about how much many of these recast actors need to look like their original counterparts, but we’re throwing that out the window here. Constance Wu, of Fresh Off the Boat fame, is our choice for Princess Buttercup. Wu most certainly has the talent to pull off the characte. The actress herself is very personable and has a strong will, speaking out about issues of diversity in Hollywood on a consistent basis. On top of this, many of the characters Wu has played share the same independent and unyielding personality of Buttercup in The Princess Bride.
2. The Grandpa – Mandy Patinkin
Up until this point we have been focused on the characters of the story within the story of The Princess Bride. Rob Reiner told his tale through a framing story; the events of the film take place within a book that an old man is reading to his sick grandson. Buttercup, Montoya, Fezzik, and Wesley are all important characters, but they wouldn’t even exist if it wasn’t for the grandfather’s narration! The Princess Bride was a book that Grandpa had read to the boy’s father on multiple occasions and he felt that it would help his grandson pass the time as he recovered from his illness.
We know that this is pure fan service, but there is absolutely no other choice for the grandfather than Mandy Patinkin, the original Inigo Montoya. At 64 years old, the actor is now the right age for this part. Despite the accent he used in The Princess Bride, Patinkin actually has a deep and soothing voice that would make a perfect “bedtime story” voice for narrating the film.
1. The Grandson – Gaten Matarazzo
Ah, Fred Savage… how young and innocent you were back then. In The Princess Bride, the character of the grandson is the under-appreciated star of the film. Think about it: if he hadn’t gotten sick, his grandfather never would have brought him over the book. And if that hadn’t happened, we never would have gotten to hear the story!
The grandson is skeptical of his grandpa’s book at first; he’s afraid that it’s going to be a “kissing book” when the book opens on Buttercup and Wesley’s romance, but he becomes more and more engaged as the story goes on. By the end of the movie the grandson wants his grandfather to return and read the story again in full the next day.
He’s no Fred Savage, but Gaten Matarazzo is our grandson for this movie. The newcomer stole our hearts in the hit Netflix show Stranger Things, where he played Dustin, the goofy coward of the group that just about everyone could relate to.
You may be thinking that at fourteen years old, Matarazzo is too old to play a believable grandson in this movie. To this, we’d point out that Gaten is only one year older than Savage was when the original film was made. Besides, movie magic can be used to make anyone seem younger. The Princess Bride is a story that has a lot of heart, so who better to be its star than the child actor who is nothing but heart?
So? Are your pitchforks out already? Who would you have cast in The Princess Bride? Let us know in the comments!
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