"Life is a tragedy when seen in close-up, but a comedy in long-shot."
-- Charlie Chaplin
Take two great voices, some red and white rotoscoped outlines of two guys talking on phones, add a lot of politics and great writing - and you have "Get Your War On".
Even though it's about 6-10 years old GYWO is one of the best short web series ever, but it's not for the faint of heart, and it might be a little dated due to specifics of the 2008 and 2012 presidential elections in the US - but this one mentions a certain someone who became the President.
Here's one of the better ones: https://www.youtube.com/watch?v=TBv3BKY_604
edit - here's a playlist of most of the GYWO clips: https://www.youtube.com/watch?v=8nhYAOWEKxE&list=PLDjrDTczwDn1tJutwWnLq23OU1JWDFAQ3
Here's another: https://www.youtube.com/watch?v=BxxETrQZwCM&list=PLDjrDTczwDn1tJutwWnLq23OU1JWDFAQ3&index=12