Initially, several A-list actors were considered for the role of Westley, including Robert Redford and John Travolta, but Cary Elwes ultimately secured the part after a successful audition.

Why it matters: Cary Elwes' charm and comedic timing perfectly embodied Westley's character, making him iconic. His casting contributed to the film's unique blend of romance and humor that has delighted audiences for decades.

The makeup used for Count Rugen's (Chris Sarandon) injuries was so convincing that it caused several reactions from crew members, who were genuinely shocked at the level of detail.

Why it matters: This attention to detail added authenticity to Rugen's character, enhancing the overall experience and believability of the film's darker moments, thereby heightening the emotional stakes.

Robin Wright and Cary Elwes had their first kiss readied after a day of shooting without prior rehearsal to capture the genuine surprise and chemistry.

Why it matters: This spontaneity resulted in a natural, heartfelt moment that resonated well with audiences and became one of the memorable highlights of the film.

The famous Cliffs of Insanity were actually created using a combination of miniatures and optical effects rather than extensive on-location filming.

Why it matters: This creative decision allowed the filmmakers to craft a visually stunning scene within budget constraints, demonstrating the inventiveness that contributes to the film's enduring charm.

Wallace Shawn improvised several of Vizzini's lines, including the iconic 'Inconceivable!' which wasn't part of the original script.

Why it matters: These improvisations added a layer of humor and unpredictability to the character, contributing significantly to Vizzini's popularity among fans.

The character of Dread Pirate Roberts was originally conceived as a collective identity passed down through generations, with Elwes embodying the character’s legacy.

Why it matters: This depth added an intriguing dynamic to the character's motivations, enhancing the theme of legacy and identity that threads throughout the story.

The Rodents of Unusual Size were created using puppetry and animatronics to deliver a unique blend of comedy and horror.

Why it matters: The mix of fear and humor in the portrayal heightened the fantastical nature of the film and captured the whimsical essence that has become synonymous with 'The Princess Bride.'

Cary Elwes and Mandy Patinkin underwent extensive sword training to prepare for their duel, learning choreography from fight experts.

Why it matters: This preparation ensured that the iconic duel was not only visually compelling but also believable, showcasing the characters' skills and dedication while contributing significantly to the film's adventurous tone.

The mysterious 'Mason's Egg' used during Prince Humperdinck's (Chris Sarandon) scenes was chosen for its unique, symbolic representation of royalty and power.

Why it matters: This subtle prop choice emphasizes the theme of power and manipulation, adding another layer to the film's satirical take on fairy tale tropes.

Robin Wright's emotional performance during the climactic scenes was often heightened by director Rob Reiner’s emotional guidance, leading her to genuinely cry.

Why it matters: Her raw emotion during these moments enhances viewer connection and serves as a testament to strong directorial support, amplifying the film's dramatic impact.

Billy Crystal, who played Miracle Max, was initially reluctant to take the role but was persuaded by his friends to accept the challenge.

Why it matters: His portrayal added a comedic essence that lightened the film’s darker moments, making the character's absurdity resonate widely with audiences.

The Fire Swamp's fiery effects were achieved using controlled pyrotechnics, carefully layered into the set to ensure safety.

Why it matters: This balance of practical effects with staged scenarios emphasized the film’s adventurous spirit, engaging viewers with its thrill and whimsical danger.

The wedding scene was filmed in a real chapel, and the priest officiating was Ruth Bader Ginsburg's uncle, which added a layer of authenticity to the moment.

Why it matters: This genuine setting contributed to the film's fairy tale feel, while also creating anecdotal interest for both fans and historians alike.

The film is adapted from William Goldman's novel, which Goldman himself narrated with a comedic tone, informing the humor and rhythm of the screenplay.

Why it matters: The script's wit reflects the original literary source, enriching the film's narrative and presenting a cleverly self-aware approach to traditional storytelling.

Certain sets were constructed on a shoestring budget, leading to creative innovations in design and visual storytelling.

Why it matters: The resourcefulness displayed by the crew resulted in imaginative world-building that lent a unique character to the film, helping it stand out in the fantasy genre.

The animatronic rodents initially malfunctioned during filming, leading to unexpected outcomes in some scenes.

Why it matters: These moments were creatively rectified, resulting in genuine reactions from actors that added to the film's humor and unexpected charm.

Many famous dialogue lines were directly influenced by William Goldman's own life experiences and relationships, leading to authentic chemistry in the performances.

Why it matters: This personal touch made the dialogues relatable and often quotable, contributing to the film's lasting cultural relevance.

Mandy Patinkin portrayed Inigo Montoya with a deep personal commitment, stating that he was driven by his own family's legacy of storytelling.

Why it matters: This emotional foundation enhanced the character’s determined quest for vengeance, creating a compelling arc that resonated with audiences.

The film underwent significant cuts during post-production, removing over 30 minutes of content that included backstories for various characters.

Why it matters: These decisions helped streamline the storyline, which ultimately gave the film its pacing and focus, ensuring an entertaining experience for viewers.

The iconic 'Battle of Wits' scene with the poisoned cups was meticulously scripted to heighten tension and humor through dialogue subversion.

Why it matters: This created one of the film's most memorable exchanges, demonstrating how wit can engage audiences while maintaining the narrative's playful tone.

The film's distinctively whimsical set designs were influenced by a blend of medieval and fairy tale aesthetics, contributing to its unique world.

Why it matters: These stylings captured audiences' imaginations, creating a cinematic landscape that has become iconic in its own right.

Despite its initial mixed reviews upon release, the film grew a cult following years later, recognized for its humor and adventure.

Why it matters: This transformation from moderate success to beloved classic illustrates the film's enduring legacy and the critical reassessment of its merits over time.

The character of Fezzik, played by Andre the Giant, was portrayed with genuine warmth, which stemmed from Andre's own real-life persona.

Why it matters: This sympathetic portrayal made Fezzik a beloved character, emphasizing the film's themes of friendship and loyalty.

The film is often described as a fairytale adventure, but it also incorporates elements of comedy, action, and romance, blending genres in unexpected ways.

Why it matters: This genre-blending approach makes the film appealing to a wider audience, contributing to its iconic status and discussion among film critics.