- The "six-fingered man", Count Rugen (who has a total of 11 fingers counting his other hand), was played by Christopher Guest, who played Nigel Tufnel, in director Rob Reiner's This Is Spinal Tap (1984). Tufnel was famous for having an amplifier that goes up to "11".
- Mark Knopfler agreed to write the music for this movie on the condition that Rob Reiner put the hat that he wore in This Is Spinal Tap (1984) in the movie. The hat appears in The Grandson's bedroom.
- The fencing masters that Inigo and Westley talk about studying are all real fencing masters from the 14th to 16th centuries (although the styles of fighting they are using have little to do with what those masters actually taught).
- Director Rob Reiner left the set during Billy Crystal's scenes because he would laugh so hard that he would feel nauseated.
- Despite his character Fezzik's almost-superhuman strength, André the Giant's back problems at the time prevented him from actually lifting anything heavy. Robin Wright Penn had to be attached to wires in the scene where Buttercup jumps from the castle window into Fezzik's arms because he couldn't support her himself.
- While rehearsing for the film, André the Giant's thick accent prevented many of his lines from being understood. To remedy this, actor Mandy Patinkin slapped André in the face to get him to concentrate harder.
- When Count Rugen hits Westley over the head, Cary Elwes told Christopher Guest to go ahead and hit him for real. Guest hit him hard enough to shut down production for a day while Elwes went to the hospital.
- The two rival kingdoms in the movie are Florin and Guilder. These are the names of two former Dutch currencies, the Florijn and Gulden.
- According to author William Goldman, when he was first trying to get the movie made in the 1970s, a then-unknown Arnold Schwarzenegger wanted to play Fezzik, and he was strongly being considered because Goldman could never get his first choice, André the Giant, to read for the role. By the time the movie was made about 12 years later, Arnold was such a big star they could not afford him, Andre was cast after all and the two big men had gone on to become friends.
- Westley's character is loosely based on Errol Flynn's character in The Adventures of Robin Hood (1938). Director Rob Reiner even used the same conversation found in "Robin Hood" for Westley: "Are you finished?" "Finished? I'm only just beginning." Ironically, in 1993 Cary Elwes would go on to play Robin Hood in 'Mel Brooks (I)''s Robin Hood: Men in Tights (1993).
- Vizzini's advice on not getting involved in a land war in Asia is derived from principles stated by Field Marshal Bernard L. Montgomery (Viscount Alamein) in a speech in the House of Lords on 30 May 1962: "Rule 1, on page 1 of the book of war is: 'Do not march on Moscow.' ... Rule 2 is: 'Do not go fighting with your land armies in China.'"
- The video baseball game the Grandson in playing during the first scene is "Hardball" produced by Accolade, Inc., in 1985. It was widely available in the mid-1980s for the Commodore 64 computer system. It was a one or two-player game. The sound was not from the actual game, but later added.
- Director Rob Reiner was the voice of the R.O.U.S.s.
- While never stated in the movie, according to the screenplay the grandson and grandfather live in the Chicago suburb Evanston, Illinois. This explains the Chicago Cubs pennant on the wall and the Walter Payton Chicago Bears jersey worn by the grandson.
- Most of the movie was filmed on location in England. The castle used for the film dated back to 1065 and had original tapestries on the walls.
- Writer William Goldman was on set during one of the flame burst scenes in the forest when Robin Wright Penn's dress caught fire. Although Goldman knew this was intentional, he was so caught up in the moment that he shouted, "Her dress is on fire!", thus ruining the take.
- The giant rodents were created with diminutive actors inside rat suits. On the day Westley was supposed to battle the giant rat, the "rat actor" was pulled over for speeding and subsequently arrested, and actually had to be bailed out of jail by the filmmakers so the scene could be filmed.
- Mel Smith (The Albino) has confessed to never having watched his performance in this film due to the painful experience involved in filming the role. His character required him to wear coloured contact lenses and, unknown to Smith and the costume department at the time, he was actually allergic to the lens solution used. This meant that Smith was in constant pain and discomfort throughout filming; hence, he is reluctant to relive the memory.
- Mandy Patinkin claims that the only injury he sustained during the entire filming of this movie was a bruised rib due to stifling his laughter in his scenes with Billy Crystal.
- Vizzini tells the Man In Black, "Never go up against a Sicilian when death is on the line." 'Vizzini' is the name of a small town in Sicily.
- Christopher Guest based his performance on that of Henry Daniell in The Sea Hawk (1940).
- While shooting scenes on top of a high grassy slope, Cary Elwes broke his toe. André the Giant couldn't walk up that hill, which was a huge slab, so he drove a rented, small four-wheeler and threw Elwes the keys to try it. Elwes went over a rock, which got caught between his toes and the pedal, crushing his toe. He couldn't delay the shoot and thus shot his scene. In the film, you can see him limping when he's running into the swamp. Costume designer Phyllis Dalton made a special shoe for him.
- During the filming of some scenes, the weather became markedly cold for Robin Wright Penn. André the Giant helped her by placing one of his hands over her head; his hands were so large that one would entirely cover the top of her head, keeping her warm.
- Cary Elwes and Mandy Patinkin performed all of their own sword-fighting after many hours of training.
- Max and Valerie, played by Billy Crystal and Carol Kane respectively, were named after author William Goldman's parents, Max and Valerie.
- There really was a "Dread Pirate Roberts" (Bartholomew Roberts) who operated in the Caribbean in the early 18th century. He is reckoned by many to have been the most successful pirate of all time.
>>> WARNING: Here Be Spoilers <<<
Trivia items below here contain information that may give away important plot points. You may not want to read any further if you've not already seen this title.
- SPOILER: Mandy Patinkin revealed that acting out Inigo's quest to avenge his father's murder brought back memories of losing his own father to cancer in 1972. He said that when filming the scene when Inigo kills "The Six-Fingered Man" he felt like he had just "killed" the cancer that killed his father.
- SPOILER: Count Rugen wounds Inigo five times before and during the period of the film: the two cheek scars he inflicted on Inigo when he was a child, sword thrusts to one forearm and the opposite shoulder, and the knife wound in the stomach. When Inigo finally gets the upper hand in their duel, he returns exactly those wounds and no more: first the forearm and shoulder, then the cheek slashes, and then finally he kills Rugen with a thrust to the stomach.
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