The Princess Bride (1987)
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Credit: 20th Century Fox

Dream Casting: The Princess Bride

Contributed by
Sep 19, 2019

Dream Casting is an imaginative look at the casting process of potential Hollywood projects based on comics and other media. This isn't just about what is being made; this is about what should be made, and who we think should be the stars.

Just this week, rumors about the mere possibility of a Princess Bride remake set the internet aflame, with everyone up to and including Cary Elwes objecting to the very idea of such a thing. Naturally, that sort of talk is catnip to Dream Casting. I'm not saying remaking The Princess Bride is a good idea; the original really is pretty perfect. But once the idea was raised, I couldn't stop thinking about who would be in it if they did. So here we are.

I'm imagining a plot basically the same as the original, with maybe a bit more edge to Buttercup, in keeping with the times. I think I've put together a cast that would work if they remade this movie. Which they shouldn't...

... but they might.

Bill Murray as the Grandfather

Bill Murray as the Grandfather

Having the story narrated by a lovable grandfather is a great device that's worth keeping, but not many actors can fill Peter Falk's shoes. Bill Murray (The Dead Don't Die) is one who definitely can.

Zendaya as Buttercup

Zendaya as Buttercup

Zendaya (Spider-Man: Far From Home) is a young actress who has that rare "real-life Disney Princess" quality, plus charisma and comic timing. She'll be a fantastic princess.

Shameik Moore as Westley

Shameik Moore as Westley

Not only is Shameik More (The Get Down, Spider-Man: Into the Spider-Verse) about as ridiculously good-looking as Cary Elwes was in the '80s, he's also a fun, dynamic performer.

Chris Hemsworth as Prince Humperdinck

Chris Hemsworth as Prince Humperdinck

Chris Hemsworth (Avengers: Endgame) looks like a real Prince Charming, which will make the awfulness of this Prince even more ironic.

Kate Micucci as Vizzini

Kate Micucci as Vizzini

Nobody but Wallace Shawn can be Wallace Shawn, but Kate Micucci (Garfunkel and Oates, Steven Universe) has a similar ability to talk fast and play things much bigger than her small size. She'll make a great Sicilian mastermind.

Paul Wight as Fezzik

Paul Wight as Fezzik

Wrestling fans know that Paul Wight (Netflix's upcoming The Big Show Show) began his career playing Andre the Giant's gigantic son. Not only is he big enough to play Fezzik, he's actually a pretty good actor.

Lin-Manuel Miranda as Inigo Montoya

Lin-Manuel Miranda as Inigo Montoya

Lin-Manuel Miranda (Mary Poppins Returns) comes from Broadway just like Mandy Patinkin did, and he brings the same kind of showmanlike energy. He might not be a great swordsman, but he seems like he'd enjoy training to look like one.

Simon Pegg as Rugen

Simon Pegg as Rugen

Simon Pegg (Ready Player One) plays a great villain, and he'll definitely enjoy chewing the scenery as the Six-Fingered Man.

Billy Crystal as Miracle Max

Billy Crystal as Miracle Max

Billy Crystal (The Comedians) still isn't quite as old as he was made up to look in the original Princess Bride, and he's so inseparable from the character of Miracle Max that I think it would be perfect to bring him back to reprise the part.

Carol Kane as Miracle Max's Wife

Carol Kane as Valerie

In fact, Crystal and Carol Kane (The Unbreakable Kimmy Schmidt) should play Max and his wife Valerie as magical characters who somehow remember taking part in the original movie, even though this would be a complete reboot, and obliquely reference it while arguing.

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