
The Princess Bride (1987)
This has to be one of the hardest movies to ever categorize. It's a fairy tale. It's a comedy. It's an action-adventure. It's a love story. It's magical, hilarious, and quite horrifying, at times. While Rob Reiner is a douche, this is a master stroke that even masters wish they had painted.
Buttercup (Robin Wright) is in love with the farm boy, Wesley(Cary Elwes), who sets sail, and is murdered at sea. 5 years later, she is to wed the pompous Prince Humperdink (Chris Sarandon), when she is kidnapped. Following her captors is the Man in Black, as they embark on a harrowing odyssey.
Although it was death at the box office, due to a terrible advertising champaign, this shimmering diamond has continued to shine brighter and brighter every year since it's release. The reason for this is it's timeless quality, it's colorful characters and the fact that it truly is fun for any age. Now take all that, and add one of the greatest sword fights ever and Andre the Giant, and you can't possibly fail.
What Makes This Movie Cool: Balancing Act. The fact that, on a relatively low budget, Reiner managed to hold together drama, egos, jokes, intrigue, pirates, love, torture and Rodents of Unusual Size, and made them work as a team. No single quality of this majestic piece is outshined or outdone. The sum of their parts was greater than any individual in front of, or behind, the camera.