The Battle of Newsweek
Back in November 2007, Markos announced on the front page of Daily Kos that he'd be writing a column in Newsweek (here's the first one), along with a politically-opposite columnist... none other than Karl Rove, neocon slime-meister extraordinaire, today's most well-known American practitioner of the politics of personal destruction.
No one asked me to illustrate this, but I did anyway, and posted it in a comment thread.
In a spatial reversal of their usual positions, that's Karl sweating on the left and Kos dominating on the right. There is also a visual nod to the evocative nickname which which Karl was anointed by George W. Bush: "Turdblossom."