What if The Princess Bride Were Cast Today?

Cary Elwes in Princess Bride

For a lot of us, The Princess Bride was a defining childhood movie. It has pirates, evil monarchs, giant rat creatures, shrieking eels, and most of all, true love. Is there any chance that it's overrated? In-con-ceivable!

It’s a perfect fairytale story where good conquers evil and love wins the day. By the time you’ve finished watching it, you can’t help but feel all warm and fuzzy.

But what if the movie were cast today? Who would play our beloved and iconic characters? Let's take a look!

11 Princess Buttercup: Margot Robbie

Princess Bride Margot Robbie

Margot Robbie has a certain sweetness about her that’s definitely reminiscent of Robin Wright, who played Buttercup. And she’s got a smile that would rival even the Disneyest of princesses.

But while Buttercup fits the role of princess to a tee, she's not only about sugar and spice. She’s also pretty feisty. At least in that sense, Buttercup is maybe a little like Suicide Squad's Harley Quinn without all the crazy (and from the trailers at least, it looks like Robbie is going to do an awesome job playing Harley).

Robbie seems like the perfect choice to portray this character, who’s a great balance of both softness and strength.

10 Westley: Chris Evans

Chris Evans Princess Bride

Westley (Cary Elwes) is basically the embodiment of moral fortitude – this is a fairytale, after all. He always seems to do the right thing, and he’s not afraid to stand up to bullies. Sound like anyone else we know? Captain America, maybe?

Westley starts the movie as an unassuming farm boy and ends it as a courageous hero, the kind of character arc Evans expertly portrays in Captain America: The First Avenger. But Westley isn’t just a generic caricature of the guy in the white hat. He shows emotional depth and vulnerability. He’s someone trying to do the right thing, despite facing unfavorable odds, and it’s this kind of conflict that has made Evans’s performances so great.

9 Inigo Montoya: Oscar Isaac

Oscar Isaac Inigo Montoya Princess Bride

How amazing would it be to hear Oscar Isaac deliver Inigo’s (Mandy Patinkin) famous line, “Hello, my name is Inigo Montoya. You killed my father. Prepare to die.”

We get chills just thinking about it. What we love about Inigo is his dauntlessness and his swagger. And Isaac has both of those covered. In The Force Awakens, his character Poe Dameron is absolutely determined to fight the First Order, and he does it with class and confidence.

Of course, Inigo hits a low point in the movie and Fezzik (Andre the Giant) has to sober him up, but he regains his swagger when he finally gets his shot to take out Count Rugen.

8 Fezzik: Dave Bautista

Dave Bautista Princess Bride

Truthfully, there’s no one better suited to play a giant than Andre the Giant. It’s in his name, after all. But Dave Bautista would probably be pretty great in the role, too. Fezzik may not be the sharpest tool in the shed, but he makes up for it with his physical strength and his big heart.

In Guardians of the Galaxy, Bautista plays a similar character in Drax, who is sometimes a little slow on the uptake, but wants to do the right thing, like Fezzik.

And while Bautista may not be as big as Andre the Giant, but he’s still got the physical stature to pull it off.

7 Vizzini: Paul Giamatti

Paul Giamatti Princess Bride

Besides having the basic look for the part, Paul Giamatti has an impressive range as an actor. He has had roles in everything from The Hangover Part II to John Adams. And a glimpse at his filmography shows that he’s played a combination of characters that would make him great for the role.

Vizzini (Wallace Shawn) is nothing if not intense, and Giamatti has demonstrated his skill at playing intense characters. But Vizzini is also completely full of himself, and that makes him a highly comedic character. Gimatti has appeared in a number of comedies, so this should be no problem for him.

6 Prince Humberdink: Steve Carell

Steve Carell Princess Bride

Humperdink (Chris Sarandon) is a stereotypical bloviating monarch, who cares only about himself. Something tells us Carell would be amazing in this role. He’s got no problem with portraying this kind of character. Just look at his work in the old Daily Show sketches, "Even Stephen," or The Office.

He’s got no problem playing characters who are convinced they’re right. Humperdink has an almost bumbling confidence that Carell would pull off perfectly (think of Humperdink smelling the supposedly scentless iocane powder). Carell’s awesome brand of comedy would bring something special to the role, and would really take Humperdink to another level.

5 Count Tyrone Rugen: Gary Oldman

Gary Oldman Princess Bride

Humperdink isn’t the most truly evil character in the movie, though. That honor goes to Rugen (Christopher Guest). While Humperdink issues commands, Rugen is the one who, for the most part, does the dirty work. He's the one who hunts Westley down in the dungeons -- and he takes a super creepy pleasure in torturing him.

So naturally, Gary Oldman would be an excellent choice. Yes, he has successfully played good guys like Sirius Black. But he really excels at playing villains, like Dracula and Zorg from The Fifth Element. He has a way of making his villains creepy and sneaky in all the best ways.

4 Miracle Max: Kevin Hart

Kevin Hart Princess Bride

Billy Crystal was amazing as the MLT (mutton, lettuce, and tomato) loving Miracle Max. The character is kooky and silly, and Crystal’s performance is one of the high points of the film. But Kevin Hart would be fantastic in the role, as well.

Although Miracle Max and his wife Valerie (Carol Kane) are certainly the oldest characters in the movie, they’re also probably the most vibrant. They’re full of energy and enthusiasm, and that’s what makes them funny. This is a type of humor that Hart would really excel at. It would be a different take from Crystal’s, but undoubtedly just as hilarious.

3 Valerie: Amy Schumer

Amy Schumer Princess Bride

Amy Schumer would be incredible in the role of Valerie, a character who doesn’t take any crap. When Miracle Max denies that Westley, in his “mostly dead” state, says that “true love” is his reason for wanting to live – a valid reason that would require Max to take action to help him – Valerie calls him on it.

And who’s better than Schumer at calling ‘em like she sees ‘em? Valerie is a funny, in-your-face kind of character who doesn't hold back. Plus, Schumer and Hart are both masters of comedy, and it would be a lot of fun to get to see them play off of each other.

2 Grandfather: Michael Caine

Michael Cain Princess Bride

Of course, the movie is really a story within a story. Buttercup and Westley’s adventures are actually the plot of a book that a grandfather (Peter Falk) is reading to his grandson, who’s sick and staying home from school.

Something about Michael Caine really epitomizes the kind, caring grandfather figure. Think of him in Cider House Rules. Even his take on Alfred was a little grandfatherly. Michael Caine would be right at home tending to the needs of a sick grandchild.

At the same time, the grandfather is quick-witted and clever, traits Caine would have no trouble conveying.  And if he did it with Falk’s New York accent, even better!

1 Grandson: Jacob Tremblay

Jacob Tremblay Princess Bride

Fred Savage at this age was the quintessential adorable little boy. He’s totally lovable as the kid who has to try to save face by pretending he cares more about his oh-so-80s video games than some dumb book his grandpa decides to read (by the end of the movie, though, he's just as riveted as the audience).

Tremblay’s performance in Room shows that he’s got acting chops, and we have no doubt he’d be able to pull this role off. And if ABC ever decides to do a Wonder Years reboot, Tremblay would be perfect for that, too. But who would we cast as Winnie Cooper? That's a topic for another article!


Any other characters you would have fun recasting from the 1980s? Let us know in the comments!

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