The Top 10 Dread Pirate Roberts Quotes

Scaling the Cliffs of Insanity. Wrestling rodents of unusual size. Battling Inigo Montoya. It’s all in a day’s work when you’re the Dread Pirate Roberts.

The Princess Bride is one of the most quotable movies of all time, and Westley’s lines are some of the very best. Some might say that’s inconceivable! But it’s absolutely true.

Here are our top 10 Dread Pirate Roberts Quotes!

“No one would surrender to the Dread Pirate Westley!”

Westley explains very plainly to Princess Buttercup that Dread Pirate Roberts is a title more than a person. In fact, the original Dread Pirate Roberts has been retired for fifteen years, happy with his pile of gold!

But pirates and sailors need to fear their captain, and nothing strikes fear into the hearts of men like the name of the Dread Pirate Roberts!

“Life is pain, your highness. Anyone that says differently is selling something.”

It takes a while for Buttercup and Westley to come together again after all these years. Westley believes that Buttercup was not loyal, and Buttercup still believes that the Dread Pirate Roberts murdered her true love Westley!

In this moment of high tension, Westley makes light of her sadness, intending to reveal that he is alive. She is livid when she says, “You mock my pain!” And yet his response gives us a glimpse at the pain that he’s endured just to return to her.

“You warthog faced buffoon….”

That may have been the first time in his entire life that Prince Humperdinck was insulted, but it certainly wouldn’t be the last if Dread Pirate Roberts has anything to say about it.

And he certainly does continue to insult him throughout the rest of the film. This particular insult provokes such beautiful imagery!

“This will all soon be but a happy memory.”

When Westley and Buttercup finally reunite, as they make their way through the murky dangerous brush Westley reassures his lady love that this too shall pass. He has certainly endured worse when he was held as a slave on the previous Dread Pirate Roberts’ ship.

This quote speaks to his optimism and cheer as a character, despite the circumstances he as endured!

“I do not envy the headache you will have when you’re awake. But in the meantime, rest well, and dream of large women.”

After a very sportsmanlike fight with Fezzik the Giant, Westley rolls Fezzik onto his back and gives him the best of wishes. He is very kind and conversational with his foes, as he hopes to make it very clear that he does not wish them any harm.

And, understandably, Fezzik is much more used to fighting large groups of people. It was almost an unfair fight!

“You seem a decent fellow. I hate to die!”

Once again, Westley has no ill will against Inigo Montoya. He knows that just like Fezzik, he’s simply trying to pay the bills!

And so, after taking a quick break and diving into a little bit of backstory, they prepare to fight to the death. It is a shame they must fight, they are both such decent fellows.

“I spent the last few years building up an immunity to iocane powder!”

In one of the movie’s most hysterical scenes, Dread Pirate Roberts challenges Vizzini to a Battle of Wits!

Over the course of the challenge, Vizzini was able to discern that only a clever man would put the poison into his own goblet, but only a great fool would reach for the wine that he was given, and he is not a great fool so, he clearly can’t choose the goblet in front of Westley. Or himself. It’s an obvious decision, I hope you can see that. Truly, he has a dizzying intellect.

Dread Pirate Roberts baffles the buffoon with a clever trick: an immunity to poison! This quote shows us just how much five years changed him and just how clever he is.

“It’s possible…”

Dread Pirate Roberts says this throughout the film on multiple occasions. When he is accused of killing Princess Buttercup’s true love he simply responds saying, “It’s possible… I’ve killed a lot of people.”

When Prince Humperdinck thinks that he’s bluffing, he concedes that indeed, “It’s possible, pig, I might be bluffing. It’s conceivable, you miserable, vomitous mass. I’m only lying here because I lack the strength to stand. Then again… perhaps I have the strength after all.”

In both cases, Westley is more than willing to concede. Cleverly, it also buys him time!

“That is what ‘to the pain’ means. It means I leave you in anguish, wallowing in freakish misery forever.”

Sometimes you fight with a sword, and sometimes you fight with your words. There are few threats better than Dread Pirate Roberts‘ threat to Prince Humperdinck.

“‘To the pain’ means the first thing you will lose will be your feet below the ankles. Then your hands at the wrists. Next your nose.

“Your ears you keep and I’ll tell you why. So that every shriek of every child at seeing your hideousness will be yours to cherish. Every babe that weeps at your approach, every woman who cries out, ‘Dear God! What is that thing?’ will echo in your perfect ears. That is what ‘to the pain’ means. It means I leave you in anguish, wallowing in freakish misery forever.”

“As you wish!”

There is nothing more romantic and sweet than Westley‘s constant willingness to make Princess Buttercup happy after all these years.

But couple that sweetness with Princess Buttercup pushing ‘Dread Pirate Roberts’ off a cliff, and you have a rather memorable revelation!

If you want to add your very own suave, swashbuckling pirate to your collection, be sure to check out the Westley AKA The Dread Pirate Roberts Sixth Scale Figure by Quantum Mechanix, complete with two detailed portraits, a wine goblet (for going in with Sicillians) and a sword that can be wielded in either hand as the battle dictates.

What’s your favorite Dread Pirate Roberts quote from The Princess Bride?