Westley (Cary Elwes)’s Timeline and Summary
- We all have to start somewhere. Westley's first gig is as a lowly farmhand on a lowly farm. Fortunately for him, his boss is hot, and has the hots for him. Guess there was no stigma about interoffice romance back then.
- He heads off to make his fortune (doing what, we're not sure), when he's captured by the Dread Pirate Roberts and nearly killed.
- Instead, Roberts trains him to become awesome in every way, eventually passing along the name and job duties to his star pupil.
- Once he's again a free man five years later, Westley returns to Florin and, his identity disguised, rescues Buttercup from a bald lunatic and his dim-witted henchmen, Inigo and Fezzik.
- He takes his true love through the dangerous Fire Swamp in an effort to escape the clutches of the Prince, who's trying to recover his fiancée. Buttercup is set on fire, nearly suffocates in quicksand and is almost attacked by a ferocious rat creature, but she still gave it 2 ½ stars on Yelp for the "romantic ambience."
- Upon emerging from the swamp, Westley's arrested by Humperdinck's men and thrown into the Pit of Despair, where he's tortured on a device called "The Machine." That's trademarked, by the way, so don't even think about trying to create your own.
- Humperdinck, who's in an especially bad mood, takes it out on Westley by turning the Machine up to 50 and (mostly) killing him.
- Westley's limp body is retrieved by Inigo and Fezzik, who take him to Miracle Max. Max gives them a pill that brings Westley back to life, even if his range of movement is initially limited to a bit of neck-swiveling and some minor eye blinking.
- With Inigo and Fezzik's help, Westley storms the Prince's castle in an attempt to rescue Buttercup before she's married to Humperdinck.
- He's too late, but he finds her right before she kills herself (she's not really into the prince so much), and then tricks Humperdinck into surrendering in spite of being still mostly paralyzed.
- (We think Humperdinck definitely got off too easy. Westley at least could have mussed his hair after he was tied up. We bet that would have driven him crazy.)
- Westley and Buttercup, accompanied by Inigo and Fezzik, then ride away from the castle and off into the sunset, which is a really popular kissing spot.