Vizzini may be an antagonist and a pretty evil dude, but he’s such a classic character. It’s inconceivable to hate him.

He hires Inigo Montoya and Fezzik to kidnap Princess Buttercup so he can pocket the gold that he was hired for.

He was surprisingly bossy for two men that could easily have killed him. But he apparently was the reason they bounced back from low points in their own personal lives.

But he has a showdown with Westley and they play the game of Which is the poison cup?

For which he loses, as they were both poisoned. Westley had spent years building am immunity to the poison put in the goblets for their game of wits.