Some of the responses to my call for examples of Obama/McCain-style Hip Black Guys vs. Cranky Old White Guys:
Spike Lee vs. Clint Eastwood (the WWII "negro" actors controversy)
This definitely fits the model, but it was an insignificant story at the time I was writing the comic, and has developed only into a slightly more than insignificant story.
Black thug vs. Dirty Harry (Do you feel lucky, punk?)
Was that thug really "hip"? And how would I fit Obama into that role?
Eddie Murphy vs. Nick Nolte (48 Hours)
How did I miss this one? I even looked up Eddie Murphy’s filmography while trolling for examples for the strip. Of course Nolte wasn’t exactly old at the time of this movie, but I’d have forgiven that for the same reason I let that slide for Simon in the American Idol panel — because the crankiness factor is off the charts.
Sidney Poitier vs. Spencer Tracy (Guess Who’s Coming to Dinner)
I considered this, but I had never seen the movie, and it seemed too boring to research.
Gary Coleman vs. Mr. Drummond (an actor vs. a character, from Diff’rent Strokes)
The black guy not hip, the white guy not cranky, but would have been very funny. And how about Webster vs. Alex Karras (a character vs. an actor)?