Character Analysis
Errol Flynn Meets Douglas Fairbanks, Jr.
Okay, we'll give you a minute or two to Google those two gentlemen.
Back already? They're pretty dashing, right? Flynn was most famous for playing Robin Hood (a role that Cary Elwes himself later spoofed in Robin Hood: Men in Tights), while Fairbanks was known for portraying Zorro, as well as other roles in exciting adventures. Including another version of Robin Hood, actually.
Apparently, you sort of have to have a band of merry men if you want to be considered a genuine swashbuckler.
When casting the film, Reiner was freaked out he wasn't going to find anyone right for the part. He needed someone who was smooth with the ladies (well, just one of them), handsome as all get out, and with an incredible sense of humor. There weren't a ton of viable options, but fortunately Elwes was coming up at just the right time, and Reiner was able to snag him.
Which is why the character of Westley is one of the coolest folks in the history of film. There are plenty of characters in Hollywood lore that were either baller (Batman, Lara Croft, Jason Bourne) or hilariously funny (Ron Burgundy, Austin Powers, Peter Venkman), but how often are they both?
Other than any part played by Harrison Ford in the late 70s and early 80s, we're drawing a blank.
But Westley is that rare, perfect mix of can-kick-your-butt-any-time-he-wants-to and can-deliver-a-one-liner-better-than-Rodney-Dangerfield. Seamlessly he goes from a thrilling sword fight to an amusing battle with a giant to fending off large rodents in the Fire Swamp to cracking wise with a man who's determined to have him killed. He also plays both unassuming farmhand and terrifying pirate.
And you thought Daniel Day Lewis was versatile.
You Gotta Have Faith(fulness)
There's no doubting the authenticity of Westley's love for Buttercup. We can't imagine a guy being more in love with a woman—and we're avid Friends fans. (How could you, Ross? A "break," our butt.)
And yet, he sure is rough on his true love when he's reunited with her after all those years at sea. After dispensing of Vizzini, we almost expect to see him whip off the mask and initiate make-out sequence. But instead he lays into her, throwing phrases like "enduring faithfulness" mockingly in her face. Seems like someone was doing an awful lot of stewing on that ship.
But is his anger justified? After all, it had been reported that he was dead. What was she supposed to do, cover her head with a paper bag, crawl into a corner somewhere and weep non-stop for the next fifty years?
And here's the other thing: it was the law of the land that the Prince could choose his Princess. It was pretty clear that Buttercup was never "into" Humperdinck, so it's not like she just had a short mourning period and then hopped right onto Tinder to track down her next beau. She likely didn't have a choice in the matter, so why did Westley have his tights in a bunch?
We tend to think that he wasn't really that peeved. Angry about the circumstances, sure, but not angry at Buttercup. He probably just wanted to play the part of the callous pirate first, to get a little information out of her before he revealed himself. Otherwise, it seems hard to believe his mood would change so drastically—and he'd forgive her so easily—once the mask comes off.
Which he does.
And besides, Westley might have been faithful over the past five years, but he was on a boat full of men. Probably a little easier for him not to stray. Not too much temptation, unless the Dread Pirate Roberts made a habit of stopping off at the Florin Hooters.
Have Mercy
When the grandson finds out that Westley lets Humperdinck live, he's more than a little annoyed.
Um, count us in.
Humperdinck survives? But why? Vizzini gets his just desserts, and Count Rugen gets sent to meet his maker. What's so special about our main antagonist that he gets to skate away, whether or not he has to "live a long life alone with his cowardice"?
Well, first of all, Westley seems to think that there are things worse than death. Okay, that adds up. As a "man of action" and soon-to-be-former pirate, our hero probably doesn't fear death all that much, aside from the fact that he wouldn't get to be with his one true love. But there seem to be bigger issues on his mind: integrity, valor, righteousness, truth. As long as he holds onto those things, his life can't be a failure, no matter how prematurely it may end.
In that sense, he probably views ending Humperdinck's life as giving the jerk a chance to take the easy way out. The death would be quick and relatively painless, and then he'd never have to account for his actions, or toss and turn at night trying to forget about all the awful things he's done.
On the other hand, by letting Humperdinck live, the Prince is now going to be without his bride, without his right-hand man, and even without that war he wanted so badly to happen. He's going to have a lot of time on his own to consider where it all went wrong, and how, when given the chance to have everything he'd fought for, he surrendered to a guy who probably would have needed some help making his way to the bathroom. That's gotta sting a little.
So when Westley chooses to let his arch-rival keep on breathin', it isn't mercy—not really. If anything, it's the cruelest punishment he could have imagined for the guy. The only thing we can think of that would have been worse is if Westley had put Gangnam Style on repeat before leaping out the window.
Westley's Timeline