The first time Stiles was introduced to The Princess Bride it was after he’d been sick in bed with the flu for days. He was eight and, after the initial misery of the illness had waned, completely bored. He was still too tired to go out to play or even stay awake for very long, but without someone to entertain him (Scott and Em were banned from the room in case they caught the flu too) those short spans where he was awake and lonely were miserable especially since his mother was on a business trip and couldn’t get home because of weather in Boston. Finally his father lugged a television and video player into the bedroom (after having to run up to the attic for said video player) and popped in an old VHS tape. Stiles whined, wanting to go outside and play not watch a boring old movie, but the Sheriff promised him that this movie was unlike any other he’d seen before.
When the movie started, with a little boy in much the same position as Stiles was, he wondered if his father was trying to make a point. Surely he wasn’t as annoying as that boy there! But he cuddled against his dad, who had surprised him by sticking around instead of going back downstairs. “I like this movie too,” his father confided in him. “And it’s your mother’s favorite.” That settled Stiles down a bit. He really wanted his mother, but maybe watching her favorite movie would make up for only having phone calls for such a long time. So even though the movie started slowly, and he felt like the boy on screen, he curled up next to his Dad and tried to ignore the urge to suck his thumb, a habit he had just left behind a few months ago. Instead he held tightly to his stuffed pirate bear and soon he was lost in the story unfolding between Buttercup and Westley. But it was Inigo Montoya Stiles liked best.
He liked Inigo best because Inigo was brave and loyal and smart. He understood Inigo best too. What did he care about love and romance and icky girls! His parents were his most important people, so he'd avenge them too just like Inigo. Plus, Inigo got to be the next Dread Pirate while Westley only got a girl. He was pretty sure he knew even at eight which was the better bargain.
After that, The Princess Bride became a staple in the Stilinski household. Stiles watched it nearly ever weekend, and more times than not his parents joined him. Soon, he could quote whole passages and would make Scott and Emery play Dread Pirates with him in the backyard. Emery refused to play Buttercup so that role fell to Scott, because Stiles only wanted to play Inigo. Sometimes Scott would have to play two roles, because someone needed to be the Six Fingered Man so Stiles could avenge his father’s death. It became a common sight to see the three of them fencing with their cardboard and tinfoil swords, and one one memorable occasion reenacting the cliff scene led to a broken arm for Stiles.
Eventually they grew out of playing Dread Pirates, but Stiles never grew out of his love for the Princess Bride. When they got to middle school and Stiles could no longer admit to his friend
s that his favorite movie was The Princess Bride (followed by Toy Story and the Neverending Story), he would still curl up with his parents once in awhile to watch the film.
When his mother died, Stiles didn’t watch the movie for over a year. His father didn’t either, and their copy of the tape disappeared and wasn’t replaced. Then one night he heard something downstairs and went to investigate. he found his father sitting on the floor in the living room, watching a midnight rerun on the television. After a few moments of hesitation he joined him, and both pretended to not notice that the other was crying before the movie hit the halfway mark. After that the Sheriff went out and bought a new version of the film, on DVD because they couldn’t find a VHS, and they watch it each year since then on Molly's birthday.
It’s still Stiles’ favorite movie, but the early childhood idolization has been replaced with a tinge of regret and sadness.