Round 1: Match 25
The Princess Bride
This one must've been a bitch to market. Part romance, part fantasy, part action, part comedy, et cetera. And it works on all of those levels. A lot of great performances, particularly by the late Andre the Giant, but the REAL star of the movie is Mandy Patinkin as Inigo Montoya, who I am still baffled didn't get any awards for the role. Also features the best sword fight scene I've ever seen.
VS
The Cabinet of Dr. Caligari
The one that started it all. The semenal horror film AND German expressionist film. The plot and acting, while both were good, are not nearly the point of the movie. The point is the look, the horrifically angled houses, the tall chairs, the jumbled mess that is the town, the nightmarish look that infects everything in the movie. There's no way the look of this movie could ever be replicated.