You know that feeling when you're watching a masterpiece and everything feels like it was meant to be? That's The Princess Bride. But if you ask the man behind the most quoted villain of the 80s, he'll tell you he spent the entire production waiting for a pink slip. The Princess Bride and Wallace Shawn are inseparable now, yet back in 1986, Shawn was convinced he was a disaster in the making.
He wasn't the first choice. Not even close.
Rob Reiner originally had his eyes on Danny DeVito. When that didn't pan out, Shawn got the call. But here’s the kicker: his agent actually told him DeVito was the preferred pick. Honestly, that’s like telling a marathon runner they’re only there because the gold medalist had a flat tire. For an actor as cerebral and self-critical as Shawn—a Harvard grad who studied at Oxford—this was psychological warfare. He spent every single day on set looking over his shoulder, certain that Reiner was about to realize his mistake and fly DeVito in to save the day.
The Battle of Wits and a Very Sweaty Sicilian
If you watch the "Battle of Wits" scene closely, you’ll see Vizzini sweating. Most fans think it’s just the heat of the Florin sun or the high stakes of the iocane powder.
It wasn't.
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That was pure, unadulterated terror. Shawn was so nervous about his performance that he was physically leaking. He kept trying to imagine how Danny DeVito would deliver the lines. He’d do a take, hate it, and then spiral into a "dizzying intellect" of self-doubt.
What’s wild is that his insecurity actually fed the character. Vizzini is supposed to be overcompensating. He’s a small man who insists he’s a genius while being outsmarted by a farm boy. Shawn’s frantic energy made Vizzini feel dangerous and pathetic all at once.
- He said "Inconceivable" five times.
- It became the third most repeated catchphrase in the film.
- He actually didn't think the movie was funny at first.
Cary Elwes later noted in his memoir, As You Wish, that Shawn was "inconsolably nervous." Reiner had to give him direct line readings sometimes, which is usually a slap in the face to a serious actor. Shawn? He took them gratefully. He just wanted to survive the day without being fired.
Andre the Giant: The Protector of Vizzini
Despite the friction of his own mind, Shawn found an unlikely protector in Andre the Giant. There’s a scene where the trio—Vizzini, Fezzik, and Inigo—are being hoisted up a cliff (The Cliffs of Insanity, naturally).
Shawn is terrified of heights. Like, paralyzing fear.
As the forklift (the 80s version of CGI) lifted them into the air, Shawn started to shake. Andre, who weighed over 500 pounds and could have accidentally crushed him, just reached out a massive hand. He patted Shawn and rumbled, "Don't worry, I'll take care of you."
It’s a beautiful image. This tiny, neurotic playwright being cradled by a gentle giant while they filmed one of the most iconic adventure movies ever made. They were a bizarre family. While Mandy Patinkin was obsessively training for his sword fights, Shawn was just trying to keep his lunch down and memorize a monologue that felt like it was written for someone else.
Why the "I-Word" Still Haunts Him
Fast forward forty years. You can't walk through an airport or go to a grocery store as Wallace Shawn without someone shouting "Inconceivable!" at you.
Does he hate it? Sorta.
He’s gone on record saying that while he’s proud of the work, he doesn't love being defined by a single word. He’s a serious playwright. He’s written deep, political pieces like The Fever and Aunt Dan and Lemon. He’s the guy from My Dinner with Andre.
But to the world, he is the Sicilian. He’s the guy who fell for the classic blunder—the most famous of which is "never get involved in a land war in Asia."
The irony is thick. Shawn, a man who truly has a dizzying intellect, played a man who thought he had one. He was so worried about being replaced by DeVito that he didn't realize he was creating something DeVito never could have: a villain who is both annoying and somehow deeply memorable.
A Legacy of Insecurity
Looking back, the casting of The Princess Bride and Wallace Shawn was a stroke of genius by Janet Hirshenson. She saw him in My Dinner with Andre and knew his specific, high-pitched delivery of "inconceivable" was exactly what the movie needed.
The film didn't explode at the box office right away. It was a slow burn. It found its life on VHS (remember those?) and became the cult classic it is today.
Shawn eventually realized he wasn't going to be fired. But that realization didn't come until the movie was already in theaters. He spent the entire shoot in a state of high-alert anxiety.
It’s a good lesson for anyone struggling with imposter syndrome. Even the people we think are icons—the ones who deliver the lines we quote for decades—are often just people terrified they aren't good enough.
Actionable Insights for Fans and Creators
If you’re a fan or a burgeoning creative, there are a few things to take away from Shawn's experience:
- Use your nerves. Shawn’s real-life anxiety gave Vizzini an edge that made the comedy work. If you're nervous, lean into it.
- Trust the director. Even when Shawn didn't "get" the humor, he trusted Rob Reiner's vision. Sometimes you're too close to the project to see the big picture.
- Collaborate with opposites. The chemistry between the tiny, frantic Shawn and the massive, calm Andre is what makes the trio work. Find people who balance your energy.
- Accept your "I-Word." You might do something brilliant that isn't what you want to be remembered for. That's okay. Success is rarely what we expect it to look like.
Next time you watch Vizzini challenge Westley to that final drink, look at Shawn’s eyes. He isn't just playing a man who thinks he’s winning. He’s playing a man who is desperately hoping the director doesn't yell "Cut" and tell him to pack his bags. That tension is what makes the performance timeless.
To dig deeper into the making of the film, pick up a copy of Cary Elwes's book As You Wish. It provides a first-hand account of the "sweaty" days on set and confirms that, despite his fears, Wallace Shawn was the only man who could have made that role legendary.