The Dread Pirate Westley

Bae Watch Wednesday: The Dread Pirate Westley

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Welcome to Bae Watch Wednesday, where I tell you all about the fictional characters you ought to be crushing on. On New Year’s Eve, I watched perennial classic The Princess Bride and got to thinking about that classic bae, Westley.

Who is Westley?

Westley is the male lead of The Princess Bride, though the movie features many iconic characters who could arguably be called the protagonist. I suppose a better way to put it would be that he is the romantic lead. Westley is the love interest of Princess Buttercup (who, in my opinion, is the real protagonist).

Buttercup grew up in Florin on a farm. She had a happy youth, but she was headstrong. She particularly enjoyed bossing around the farmhand who worked for her family. That farmhand was, you guessed it, Westley. Despite her bossiness, however, he fell in love with Buttercup and displayed that love by agreeing to whatever she asked — “as you wish.”

However, Westley was poor. He did not want to marry Buttercup until he had made his own way in the world. To do so, he set out by sea to make his fortune. Sadly, his ship was attacked by the Dread Pirate Roberts, who everyone knows takes no captives. Buttercup is broken-hearted by her love’s death and swears never to love again.

The Princess

When next we see Buttercup, she is engaged to the prince of Florin, Humperdinck. She is beloved by her people for her beauty and kindness, but she is unhappy. She does not love Humperdinck and takes solace in escaping the palace. On one such jaunt into the wilderness, she is kidnapped and taken away by three men: Vizzini, Fezzik, and Inigo Montoya.

The three captors are shocked to realize that they are being followed. A man in a black mask is tracking them. One by one, they attempt to get rid of him. Inigo, a master swordsman, duels him. The man in black beats Inigo and leaves him unconscious. Fezzik, a giant tries to best him in hand-to-hand, but the man in black uses his smaller size to his advantage and again is successful, leaving Fezzik unconscious as well.

Finally, the man in black faces off against Vizzini, the genius behind the plan. They have a duel of wits, where Vizzini tries to rig the game. Luckily, the man in black manages to outwit the genius. Vizzini dies, and Buttercup finds herself rescued by the unlikeliest of sources.

Buttercup heads off with the man in black. She displays some of her former fire, showing that despite her change in circumstances she hasn’t changed in personality. She wonders at the man in black’s actions and thinks things through. However, Buttercup is also still fiery and attacks the man in black when she realizes who he is: the Dread Pirate Roberts, the man who killed her love.

The Dread Pirate Westley

Except… it turns out that Roberts did not kill Westley — Roberts is Westley. For once, Roberts broke routine and took a captive. Westley pleaded for his life, not for his own sake, but so that he could return to Buttercup. This captured Roberts’ attention, and he kept Westley alive, though he promised to likely kill him soon.

Over time, however, Westley not only remained alive but proved himself skilled and talented. Roberts grew fond of his captive and saw his potential. To Roberts, here was a man who could potentially take on the role of the Dread Pirate Roberts, which turns out to be a title rather than an actual name. Roberts decides to retire and gives Westley command of the Revenge.

Having successfully made his way in life as a pirate, Westley returns to find that Buttercup is engaged to another man. He needles Buttercup, but when she mentions that she never stopped loving him, he reveals the truth. They attempt to escape Florin and Humperdinck but are captured. Westley is taken to the Pit of Despair, where Count Rugen performs experiments on him. Eventually, Humperdinck murders Westley out of jealousy.

However, death cannot stop true love. Westley is revived with the help of Inigo and Fezzik, who want his help to kill Rugen. They break into the castle, rescue Buttercup, humiliate Humperdinck and kill Rugen. They then escape on four white horses, and Westley seems to pass on the title of Roberts to Inigo.

Why is Westley Bae?

This man is like the iconic hero. Swashbuckling and dashingly good looking, he represents the mysterious bad boy and the loving hero all in one. True, it’s been some years, but 1980s Cary Elwes was a babe. It’s easy to see why anyone would swoon over this pirate.

As You Wish

Not only is Westley good looking, though, but he’s also a romantic dream. The iconic line — “as you wish” — is wonderfully written, and well-delivered by Elwes in a way that doesn’t ring false. Westley loves Buttercup, more than anything. That is his primary motivation throughout the film, though there is a dash of revenge when he fears his love has been scorned.

The way that he treats his love is wonderful. At first it’s a bit milquetoast, with a sweet farmboy falling for a beautiful girl. When he returns as the Dread Pirate Roberts, however, Westley becomes a lot more interesting. He’s suave and debonair, as befits a world-famous pirate. But he doesn’t treat Buttercup as if she is lesser because she’s from his quieter past.

Instead, their new relationship is based on mutual respect. Westley respects Buttercup as a princess and his love, and she respects him as a well-traveled, worldly person. He helps her through the fire swamp but doesn’t treat her as if she is dainty and fragile. It’s simply a matter of him having more practical skills that help with survival.

They also have a great witty repartee that makes their relationship more endearing. “As you wish” comes up, but instead of simply saying “as you wish” and doing whatever Buttercup says, Westley has a personality now. He tells her funny stories of his time away. He’s snarky as hell throughout the movie, but especially when he talks to Buttercup.

Buckle My Swashes

Westley is great on his own, too, though. He may be a romantic dream, but he’s also a freaking cool pirate. Sure, at first really all he had going for him was his looks. As a farmboy, he really was quite bland. But now that he’s seen the world, experienced things learned new skills, Westley is pretty badass.

He can beat every opponent at their own skill set. Inigo is one of the greatest swordsmen in the world. He has studied swordplay exclusively for twenty years. The “man in black” can defeat him. Faced off against a giant, Westley uses what should be his weakness — his size — as his path to victory. He realizes that he needs to use what he has at his disposal.

The duel of wits with Vizzini is great. You are led to believe that the “man in black” is smarter than Vizzini, even though Vizzini cheated. But he later reveals that he had rigged the game himself, ensuring that he would win and Vizzini would die. There’s a real sense of satisfaction that comes from watching him outmatch this snide genius.

Later, Westley shows off more skills. He survives the fire swamp and its perils, endures horrific torture, comes back from being “mostly” dead, and still manages to bluff his way into forcing Humperdinck to surrender. He is massively multitalented, for which we have the former Roberts to thank.

When Westley rescues Buttercup at the end, it seems fitting. This is a character that has grown and learned, developed from a milquetoast farmboy to a kickass pirate, all in the name of true love. He is snarky, sarcastic, and deadly skilled.

What’s Not To Love?

The Princess Bride is iconic. It’s a thoroughly enjoyable movie that has only gotten better with age. It’s also perhaps the most quotable movie in history, and many of the best lines come from Westley. Ranging from the sweet “as you wish” to the scathing “life is pain, highness… anyone who says differently is selling something,” there’s a line for every situation under the sun.

Westley is witty and fun, but he’s also romantic, swashbuckling, kickass, talented, and a deadly pirate. He’s such a multifaceted character. Deep down, however, the core of his character is his love for Buttercup. It defines every action, every thought we see in the movie. He never gives up on her, and through watching him, we learn to never give up on true love either.

I’ve seen The Princess Bride dozens of times, and I’ll likely watch it dozens more. And every time I watch the movie, I swoon over the Dread Pirate Westley, who won’t let death stop him from being with his true love.