Have you ever listened to a drunk friend try to tell you a story? Remember how they can't really remember the story, and get distracted by fun things like say... pants? Let's be honest you have, and it was hilarious. Well Jeremy Conner decided to take those stories and make them into short films. There's a twist - he gets bona fide historians, and then convinces A-list celebrities to act out the drunken story. The result is brilliant and extremely funny.
I think that this concept works because it is the opposite being singular (the concept Jacob mentioned in his previous post). That drunken friend is a universal story, and most people can relate to what they're seeing on screen. You aren't seeing one persons vision (or acid trip) you're seeing a societal experience. By 'interviewing' the historian, the whole concept of the interview becomes convoluted as well, and plays off of our expectation of a gray haired professor rambling on in monotone. Instead the audience sees an historical event as if it took place in the United States of Funny or Die. Simultaneously playing to and against our expectations works together to be surprising, ridiculous, and oh so funny.
Of course, the star power of this film can't be forgotten either. The production value is clearly high - the pantomime and acting is flawless, the music is perfect, and the editing is seamless. The big names and professional quality of this unknown filmmaker is pretty astonishing, and certainly is part of the draw. Will Farrel as Abe Lincoln? Don Cheadle as Frederick Douglas? The roles they play are hilarious own their own since we are familiar with their previous work, and the historical persons they are playing. The intersection of the two results in hilarity, once again because of its absurdity. The trashed narrator creating the scenario around all these characters, providing them with ridiculously inaccurate dialogue, further amps the absurdity, and is the icing on the cake.
The internet is the perfect venue for this film because it distinguishes itself. The majority of (legal) films and clips on internet tend to be of low quality, so films that have star power, high production value, and are well made stand out. This film has all three, and is made exclusively for internet, drawing attention to it.
An interesting side note: Although this films says 'funny or die exclusive' it was not originally on funny or die.
Also - Don Cheadles hair. That is all.