How can I make Westley from The Princess Bride in D&D 5e? [closed]

Question

OK, so I just got done listening to As You Wish, the memoirs of Carey Elwes about the making of The Princess Bride. Naturally, I wax nostalgic.

It got me thinking, in D&D 5e, how would one make a human (incl variant) character (of any level), starting with Standard Array or Point Buy, that can actually and effectively pull off the challenges Westley faced in tracking down and rescuing Buttercup? I'm thinking specifically of the events when he first comes on the scene as the Man in Black through the Battle of Wits with Vizzini (which, in hindsight I think was probably a Wisdom contest couched as an Intelligence contest).

My first thought is a Swashbuckler Rogue with a Pirate background. That covers the Athletics (climbing the Cliffs of Despair; possibly one boosted with his Expertise), Perception (not part of this challenge, but demonstrated later in the movie), and skill with boats.

That covers him through the start of the fight with Inigo. The fight with Inigo is mostly about just skill with the blade, which we can explain through level differences, stat differences, or class differences (e.g. if Inigo is a Dex-based Fighter and Westley is a Swashbuckler, Westley will have the edge if they're both unarmored due to the special Sneak Attack that would be in play in that scenario). One could argue that he demonstrates Acrobatics in that scene as well, however, so one of his Rogue skills would have to go to that.

The fight with Fezzik seems mostly a grappling fight, which means Westley would probably need to have a decent Strength to actually win. Though I suppose a high enough Dex draws the fight out long enough that he eventually wears the Giant down. I'm not familiar enough with the Grappling rules to make the call here, help is appreciated.

Finally, the Battle of Wits is tough for me to model in-game. Is there a non-homebrew way to have and use a poison strong enough to kill an opponent while also ingesting it yourself and not having any ill effects? I guess successful Save or Die rolls (if such a poison exists) would let Westley live, but if you're really modeling the scene Vizzini takes (and fails) those saves, or takes massive HP damage from the poison, while Westley is never in any danger.

I hope this doesn't seem like multiple questions or too broad; the main thing I'm trying to ask is how to model a well-known character from film over a fixed set of scenes. I also don't think it's opinion-based, as I'm asking for actual rules for resolving the challenges he faces.

I honestly didn't think this was "primarily opinion based", so perhaps my wording is unclear. What I'm asking, specifically is:

"What D&D 5e rules/character build will allow me to create a human character that satisfies the main challenges that Westley overcomes in his pursuit of Buttercup? Specifically, he has to be able to handle ships, climb walls, beat a swordmaster in fencing, beat a giant (or at least exceptionally large/strong human) with grappling, and trick someone into drinking a rare poison while imbibing but not suffering its effects himself. I'd prefer RAW if they exist."

Answer 1

It sounds like you've already mostly answered your own question. The only lingering doubts seem to center around the iocane powder.

Since this is a single poison and not "all" poisons, I'd handle this via Bluff checks (as recommended in the comments). This isn't a knowledge/etc. skill, since he's not a trained assassin or poison maker. And his Bluff would get a bonus because he is relying on the reputation of Dread Pirate Roberts, a reputation that he banks on often since Roberts is more "franchise myth" than person at this point.

I would suggest that he have a fairly high CHA score, along with the comment suggestions for high STR and DEX. In fact, I would guess that WIS would be his "dump stat," given the foolish decisions he sometimes makes. Like running away from his one true love to seek his fortune and hiding in the fire swamp.

As GM, I'd want the player to have talked over the Iocane Resistance with me well before he had any idea that the "battle of wits" encounter was coming. At that time, I'd probably set up a thing along the lines of a bonus to the poison saving throw. Something like a +10. That would be sufficient to probably keep him alive against a small dose, but not enough that he could ignore it with impunity at all doses.

The text from the Iocane wikipedia article linked above is:

A deadly Australian poison, odorless, tasteless and highly soluble, used by the hero Westley in his 'battle of wits to the death' with Vizzini. Is available in a powder form, which Westley used. Although it takes a few years, the human body is capable of building an immunity to the poison.

I would stat the poison as

Iocane Powder (ingested) A creature subjected to this poison must make a DC 15 Constitution saving throw. On a failed save, it takes 6d6 poison damage and is poisoned for 24 hours. On a successful save, the creature takes no damage and isn’t poisoned.

Though an argument could be made that the poison isn't deadly, but just causes unconciousness. I mean... no one checked his pulse in the movie...