239 Questionable-Judgment Theodore Stomachbrace
I'll admit, I'm fibbing the date on the post and adding this one late. Here's my version of John Hodgman's Questionable-Judgment Theodore Stomachbrace.
I was happy with this one, which mixes raster and vector (Teddy's silhouette was done in Inkscape and copied into the Photoshop doc). The silhouetted hobo is an homage to Apelad, while the whole thing is an homage to Dutchboy, whose earlier version of the same hobo cracked me up.