Oh! Oh! Who's Buttercup?! Who's Inigo? Who's Fezzik?
Supernatural 2: Why is it our job to save everybody?
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My casting would be:
Castiel=Buttercup
Sam=Inigo
Fezzik=Bobby
Inigo is Gabriel, Fezzik is Sam, Dean is Buttercup. Chuck is Miracle Max. It fits creepily well in places, other places it's more distant. It's a fusion, but they're still battling the apocalypse so there's a lot of canon in it.
Fezzik is Sam
Perfect.
Fezzick is Sam?! Heh. ♥
Who's Vizzini?
Crowley as Vizzini?
It's funny, as I read it, I rewrite it to make it even more like the movie. The first time, some of the stuff went under my radar. But now I can almost hear the soundtrack at times.
Crowley is pretty much VIzzini, although that's a less defined mapping.
Maybe if it wasn't Crowley, but Mark Sheppard playing Manservant Neville, what with the scenery chewing.