Revealing mistake: When Leo is laying his dead kids on the grass, the little girl keeps moving her eyes and breathing.
Revealing mistake: In the very first scene, when Teddy and Chuck meet, they are standing on the bow of a ship traveling at full speed (as the Captain wants to return to the mainland before the storm hits), yet their lapels don't so much as flutter. Even at a slower speed, there would be some movement from the air as they passed across the water.
Continuity mistake: When Teddy's kids are lying dead on the grass, the position of the girl's arms keeps changing between shots.
Teddy Daniels: Baby, I love this because you gave it to me, but it is one fuckin' ugly tie.
Trivia: During the ferry approach at the start, we are shown Shutter Island. In actuality this is a combination of Peddocks Island (the decaying brick buildings), Maine's Acadia National Park, Massachusetts' Medfield State Hospital, and Turner Hill Country Club's Rice Estate (located in Ipswich, MA), which were combined via CGI. Additionally, the mountainous region of the island (shown as the ferry approaches) was also CGI, and added in post-production.
Question: The woman that writes "run" on Teddy's note pad, was Ben Kingsly trusting this "crazy woman" not to tell Teddy or even let it slip that the whole thing was set up for him? Same question goes for every other crazy person in the institute that Teddy speaks to.
Chosen answer: The other patients were not let in on the arrangements. They would have had no reason to suspect that anything at all had been set up for Teddy. As far as they're concerned, if they're cognizant enough to be concerned at all, Teddy's just another crazy guy acting as crazy as all the rest of them.
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Answer: Teddy belonged in Ward C. He would have never met any of the patients.