Logorama, the Oscar-winning short film by H5/François Alaux, Hervé de Crécy and Ludovic Houplain, tops the list. I've watched it three times in a row, and it is the most brilliant thing I've ever seen. They made something that I've thought about making for the longest, and they did it with style, humor and intelligence.
There are over 2500 logos and other relics of our obsession with pop culture and corporate symbolism in the film. You can see how our world is literally made of trademarks. It's frightening. Every single little detail in the film is a logo. Every one.
I'll let the creators do the talking about the inspiration and the vision behind the film: "Logorama presents us with an over-marketed world built only from logos and real trademarks that are destroyed by a series of natural disasters (including an earthquake and a tidal wave of oil). Logotypes are used to describe an alarming universe (similar to the one that we are living in) with all the graphic signs that accompany us everyday in our lives. This over-organized universe is violently transformed by the cataclysm becoming fantastic and absurd. It shows the victory of the creative against the rational, where nature and human fantasy triumph."
The ending is what's most powerful. I don't want to play spoiler, so just watch this 17-minute mindfuck. I promise you that you won't regret it. Props TSS.