Cary Elwes did not receive an Oscar nomination for portraying Westley in The Princess Bride.
As I have written before The Princess Bride is an effortless delight of a film, however its success is an unusual one. In that it manages to both subvert the idea of the heroic fairy tale while also wholly embracing all the same. These contradictions in a way should not add up yet they do, and one key element of this is the pitch perfect casting throughout the film. A central thread in this tapestry is Cary Elwes himself as our hero Westley who goes from stable boy to heroic pirate of sorts. Now Elwes doesn't have as emotional of a part as Mandy Patinkin as Ingio Montoya, nor is he as comedic as the villains of Chris Sarandon as Humperdink or Wallace Shawn Vizzini, nor is he the idiosyncratic wonder that is Andre the Giant as Fezzik. His role actually is that of a typical adventure film, not at unlike the role Errol Flynn played in the 30's and 40's. Elwes even bares at least a minor passing resemblance to Flynn as a type. Elwes though is given a harder task that Flynn had in that he must be almost the embodiment of the tone of the film itself, which though light is actually quite tricky.
Now on the outset Elwes is there for a visual establishing point, as the "as you wish" exclaiming stable boy who does anything old Princess Buttercup (Robin Wright) commands. That visual being, for the lack of a better word, and I mean that!, a dreamboat. There is more to this than meets the eye though as even his method of saying "as you wish" needs to be more than it is. What I mean by that is that this could be a overdose of corn, it really should be, however Elwes even in this line develops something, something key to his overall performance, that is this sort sly earnestness. As even as he says "as you wish" there is a sincerity in it absolutely, yet also in his little glance he almost seems to say to the audience "yeah this could be little much, but it's also just right". Of course that is only the introduction as Westley disappears, supposedly killed by pirates, leaving Buttercup to be married off to the evil Humperdink, but only first to be kidnapped by the schemer Vizzini and his two good natured henchmen Ingio and Fezzik. The one man who comes to the rescue is dressed all in black, and if anyone has a particular good eye sight, or even hearing they'll notice this dashing young hero is of course the long lost Westley.
This leads to another of Elwes's challenges as he portrays the unknown hero initially facing off three challenges in order to save his one true love. Now here he is no longer the unassuming stable boy, but rather the assured hero. This brings the challenge to be both effortlessly confident and charming, while also doing that whole sly earnestness. Elwes indeed captures a natural confidence that makes Westley a most endearing hero. He however never comes off as smug despite this supreme confidence, balancing it so beautifully with this certain purity of manner that he delivers that allows this confidence to be as brimming as it is. This goes in the tone of the film that Elwes's work is an essentially part of. This being both wholly embracing the fairy tale yet also making fun of it. Elwes has this certain knowing quality in his work, particularly in his overtly comedic moments such as his showdown with Vizzini, yet even then still Elwes never goes so far as to truly mock. He nearly winks but never mocks. More importantly he provides that strict sincerity within his work particularly in regards to the central romance with buttercup, which Elwes supports with his every fiber.
Of course in a way we get a beautiful turn on this though in the film's third act, when Westley is mostly dead via a torture device and along with Ingio and Fezzik must save Buttercup from the fiendish Humperdink. The turn being that Westley is dead essentially in body yet still has his mind to contend with the evil Prince. This leaves Elwes to physically play the part of dead weight physically, along with few hilarious moments of wailing anguish, while maintaining that brimming confidence in his eyes and expert delivery. Again it creates this fantastic combination between both making fun of this sort of hero, while also wholly being such a hero all the same. It plays with the idea brilliantly as Elwes is indeed both playing with the ideas of the romantic swashbuckler, yet never disregarding them. He's flopping around like a dead body, but still exuding that charisma of a proper a hero. The best moment of this being when he directly confronts Humperdink without drawing blood. Elwes is sitting the whole time yet his persuasive eyes, and assured manner as he describes the "pain" he will bring to Elwes grants such a conviction. When he finally lifts himself to deliver the most dramatic "Drop your sword" moment, in that moment Elwes truly is the magnificent hero, and wholly earns the moment both as a fully earnest one, but also convincing in terms of Westley's victory. Of course he's also hilarious in his near collapse a moment after that victory, which in a single scene shows how wonderful this performance is. Elwes is perfectly cast, however his work goes beyond that. His performance walks this tightrope without fail to make Westley both an essential comedic element in the subversion of a high fantasy, but also purely realizing that fantasy for all its worth.
