Round 1: Match 7
The Matrix
For better or worse, the shape of both sci-fi and action films today owe a lot of their style to The Matrix. Perhaps not the best action movie, but arguably as infulential on modern action as Die Hard was to the "classic" action movies.
VS
Office Space
In my opinion, the best office comedy (including TV shows) ever. A star-making performance by Ron Livingston, at least one memorable quote per scene, and the genius idea of that rap soundtrack all make this movie the sleeper little gem it is.