Director Errol Morris, who has several amazing documentaries to his credit (Fast, Cheap and Out of Control; Fog Of War; the current Standard Operating Procedure) worked with members of the advertising and production industry to create peopleinthemiddleforobama.org -- a collection of videos presenting people who consider themselves in the 'middle', and are supporting Barack Obama for President.
While I'm more in the John Oliver school of thought when it comes to undecideds this late in this election, the reality is there are people who are still weighing how to cast their vote. With the McCain/Palin campaign throwing everything they've got into turning the choice into extremes--"pro-America" vs. "anti-America"--these interviews help get the message across that the only extremism is the rhetoric of McCain/Palin. In their own words, people who consider themselves in the middle of the American political spectrum talk about how and why they came to realize that Barack Obama is the best choice for all Americans; left, right and middle.
Being a socialist/communist/anti-American Kossack, the undecided voter friend you have may take this into account when you're working to get their vote. Morris and company's interviews may be just the thing they need to hear: People from the middle making the case. I hope you'll find it useful.
peopleinthemiddleforobama.org
Disclaimer: I know one of the people involved in making this happen, and promised I'd do what I can to spread the word about it. Also, the only Errol Morris movie I've seen is part of "Fast, Cheap and Out of Control". I swear I'm going to get around to watching the rest of it someday.