Movies and television serve to inspire DMs as we dream up new ideas to run our players through. The Princess Bride is a movie that, on top of providing great drama, incorporates humour into its narrative. The movie will never get old, remaining fresh and entertaining. So, as I reminisced about the Cliffs of Insanity, the Fire Swamp and true love I pondered… could this be turned into a skill challenge?

Of course, the answer is yes, and so I present in all its down and dirty glory The Princess Bride (only the good parts) via skill challenge.

Challenge One: The Cliff’s of Insanity

You must climb the cliff. Fortunately, there is a rope already hanging that you may use.

Complexity: 1 (4 successes before 3 failures)

Primary Skills: Acrobatics, Athletics, Endurance, Perception.

• Athletics: Use this to climb.
• Acrobatics: Use this to swing on the rope.
• Endurance: Use this to make sure your arms don’t get tired. Andre the Giant must have had a +30 to his Endurance check.
• Perception: Use this to make sure you don’t get caught off guard when the rope gets cut. You didn’t fall? Inconceivable!

Challenge Two: Buy Time Before the Fight Starts

You made it to the top, but now there is a crazy Spaniard blocking your path. You’re tired from the climb and will need time to get ready.

Complexity: 1 (4 successes before 3 failures)

Primary Skills: Acrobatics, Bluff, Diplomacy, History, Intimidate

• Acrobatics: You do some fancy footwork to distract the enemy. Don’t over do it though, remember you’re tired from the climb.
• Bluff: You trick the opponent into thinking you are left handed by practicing a few sword moves.
• Diplomacy: You engage the Spaniard in some witty banter. He mentions something about his father and a man with 6 fingers, weird.
• History: You notice the beauty of the Spaniard weapon and inquire as to its origins.
• Intimidate: You try to convince the Spaniard that maybe he should just let you pass; after all you are a Dread Pirate. Aren’t you?

Challenge Three: Dodge the Rocks and Wrestle the Giant

You beat the Spaniard, but now the giant is throwing rocks at you and apparently he’d like to wrestle as well.

Complexity: 2 (6 successes before 3 failures)

Primary Skills: Acrobatics, Athletics, Endurance, Perception, Grapple

• Acrobatics: You dodge out of the way.
• Athletics: You jump out of the way.
• Endurance: Being hit by a rock doesn’t hurt that much.
• Perception: Is that a rock flying through the air.
• Grapple: Time to apply a choke hold.

Challenge Four: Iocane Powder

Two glasses of wine, one of them poisoned. The battle of wits has begun, which glass has the poison and who will be drinking it?

Complexity: 1 (4 successes before 3 failures)

Primary Skills: Bluff, Nature, Perception, Thievery

• Bluff: You try to get your opponent to give something away. It won’t work. But it has; he’s given everything away.
• Nature: You know how the poison works, perhaps that can save you.
• Perception: Did you see your opponent poison the glass?
• Thievery: You switch the glasses.

Note: If you tell the DM at any point in this challenge that you have spent the past several years building up immunity to Iocane Powder you automatically succeed at this challenge.

Well that’s my take on The Princess Bride as a skill challenge. A little silly, but still a fun trip down memory lane. I hope you have fun storming the castle.