In going through my archives I just rediscovered a couple of nice resources for teaching about politics through the use political cartoons, videos, and primary resources.
Running for Office is an online exhibit of the political cartoons of Clifford Berryman. Berryman is probably best known for his cartoon featuring Theodore Roosevelt having compassion for a bear cub. That cartoon inspired the creation of the Teddy Bear. Berryman drew political cartoons for Washington newspapers for more than fifty years.
The National Archives has put together a fifty-two page online exhibit of Berryman's cartoons. The cartoons chronicle the process of choosing the President. The exhibit also includes cartoons about running for Congress. Running for Office does a good job of explaining the meaning and historical context of the cartoons. Almost all of the cartoons in the exhibit can be downloaded for free.
The Living Room Candidate is a great resource for teaching lessons about the role of media and advertising in political campaigns. The Living Room Candidate has a good resource page for teachers which provides a series of eight sequential lesson plans. The Living Room Candidate could also be a good resource for anyone that teaches a media studies course as your students can easily watch the evolution of television advertising through the 20th Century. The Living Room Candidate has videos of almost every Presidential campaign commercial from 1952 through 2008. A video of one of Kennedy's campaign commercials from 1960 is embedded below.
Cartoons for the Classroom is a service of the Association of American Editorial Cartoonists. Cartoons in the Classroom offers more than one hundred lesson plans based on editorial cartoons created by the members of the AAEC. Each lesson plan is available as free pdf download. As you might expect, most of the lessons deal with current political and economic topics, but you will also find some lessons that are not time sensitive.
In addition to lesson plans Cartoons for the Classroom provides links to other cartoon resources. One of those resources is the Opper Project. The Opper Project provides lesson plans for teaching history through editorial cartoons.