Here are four Obama illos from the campaign, in chronological order. The first was drawn in September 2007 for Aaron Huffman at The Stranger.
The drawing of a monitor bursting with candidates was for John Elsasser at PRSA's The Strategist in January 2008. A note about this illo: originally, this drawing had Law & Order's Fred Thompson at the top of the group, but just as I was turning in the final art, Thompson dropped out, and Mike Huckabee was on the rise. I did a quick revise, patching in Huckabee's head over Thompson's.
The drawing of Obama painting himself into a corner was a cover illo for C&E Politics, drawn in June 2008 for Jeff Brown. The original concept had Obama and Hillary Clinton engaged in a squabble over who'd slung the most mud. I thought this was a stronger concept, but for whatever reason, the folks at C&E Politics opted for a solo Obama.
Finally, at the close of a Summer laden with cinematic superhero blockbusters, we have Obama and McCain clad in brightly-colored spandex. This was a cover illo for Creative Loafing Tampa, drawn for Jason Hatcher in September 2008. This drawing was a real treat; not only did I get to draw the candidates, but I got to have a crack at few iconic superheroes, which is always fun.