"How do you analyze a political cartoon?"

So from what I know, I believe that one should go at a political cartoon the same way one would analyze a poem or work of art. Start by pointing out the obvious, making simple observations about the images of the cartoon. Then, continue by identifying what those observations could symbolize in the context of the cartoon. From there, you can infer what the artist is making a statement on, and determine what that statement is.

http://www.loc.gov/teachers/classroommaterials/presentationsandactivities/activities/political-cartoon/cag.html

From what this guide says, I was pretty close to the actual way of doing it, but one major thing I forgot is exaggeration. Political cartoonists use exaggeration as a way to identify specific people by using the most defined features and making them more defined.

Philippines Conflict Political Cartoon

Spanish American War Political Cartoon

Colonization Political Cartoon

1. Some of the first things I noticed about this cartoon were that it made a clear distinction of who represented who. It has Uncle Sam on the left, Emilio Aguinaldo, the leader of the Cuban rebellion, on the group (made clear by his hat on the ground next to him), and the man in the back is Spain. The cartoon also contains a subtitle that is difficult to read, which is from Uncle Sam to Aguinaldo saying, "See here sonny, Whom are you going to throw those rocks at?". This subtitle emphasizes the patronization of the US towards the Cuban rebellion force. The image also shows the power that the US has over Cuba by the physical stature of Uncle Sam. 

2. This cartoon illustrates the United States "protecting" Cuba from Spain as we entered the Spanish-American War. It shows Uncle Sam, representing America, protecting a woman with a label "Cuba" with an American flag, from the Cuban patriots. There isn't too much to say about this one, but it is clear that this represents the United States helping the Cuban rebellion against Spain. 

3. This last cartoon is about effect colonization has on the country as a whole. The artists makes it very clear that colonization is holding down the bird that represents the country's freedom, and that the bird cannot fly without both wings. It also emphasizes that Uncle Sam, who in this case represents the US government, is neglecting the broken wing, and is only paying attention to the perfectly good wing.