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Inigo Montoya

We can all agree that The Princess Bride is a great movie, right? The contrarians can just skip ahead to the final choice, because if you’re not a fan…well, I’ll just cry a bit for you folks. Anyway, now that we’ve got just the fans here, I’ll be honest: it’s a bit hard to choose Inigo Montoya, the gifted swordsman out for vengeance, over the other great characters in The Princess Bride, but think about the possibilities: the movie ends with Inigo being given the great honor of being the Dread Pirate Roberts by Westley, the previous holder of the title. Now, despite how the character is initially described, this guy’s not so fearsome: it’s all about maintaining appearances and seeming scary, instead of actually being scary. So Inigo, while a deft hand at the sword, wouldn’t be a menace in this new movie. He would, however, be a badass pirate.

Frankly, a spin-off starring Inigo as the Dread Pirate Roberts wouldn’t need to feature any of the other characters. I mean, it’d be great to see Westley again, but do we need to see him? Inigo could certainly face down Prince Humperdinck, but let’s get some fresh villainy in here. There are whole new characters to introduce here: who would ride with Inigo on his new ship? What would they try to pillage? Who would they try to recruit to their cause? There are stories aplenty here, even if we’re never going to get them. Who could play this iconic role, and pull it off nearly as well as Mandy Patinkin did? If Sam Rockwell could do a believable accent, maybe he could pull it off, but it’s iffy. This one’s a pipe dream, but a nice one; until someone comes along who’s the next Inigo, we’re just going to have to wile away the days and wonder what could have been.

Jules Winnfield

“First, I’m going to deliver this case to Marcellus, then, basically, I’m going to walk the Earth.” “What do you mean, walk the Earth?” “You know, like Caine in Kung Fu.” Pulp Fiction is one of the best movies ever made, and Jules Winnfield is easily the film’s best character in a sea of already dynamic and fresh characters. Jules is a hitman who’s becoming reformed by the film’s last storyline. Though he uses force to get out of a robbery, Jules doesn’t do so with his gun, and wants to move onto a better part of his life. Quentin Tarantino, the film’s writer and director, has often opined that he’d love to do a film about the Vega brothers, played by John Travolta and Michael Madsen (yes, apparently, his character in Reservoir Dogs is a Vega). But why not Jules? It’s certainly not something we can attribute to Tarantino and Samuel L. Jackson not getting along, as they’ve worked since that film.

It’s also not something having to do with Jackson being picky with his movies. Though the man could a) beat my ass without breaking a sweat and b) can be an excellent performer, he was in a movie about snakes on a plane. I don’t think Jackson phones it in, but his taste in films is questionable, at best. Nowadays, he’s going to be appearing in Marvel movies as Nick Fury, but all that proves is that he’s still enough of a badass to be Jules Winnfield again. What did Jules do after he and Vincent left the diner? We know that Vincent would end up in an apartment bathroom, soon to be shot by Bruce Willis. We know from the chronology of the film that Jules goes to meet Marcellus after the diner, but what next? The adventures of Mr. Winnfield could easily make up a series of movies, let alone one. Walking the Earth could be plenty entertaining, guys.

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