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."