Looks like I'm on a Sideshow Bob kick right now. Why? Dunno. I've always liked him, yeah, and you gotta admit, he IS über sexy with all that hair you could get lost in for weeks, and that voice that can tell you to f--- off and still manage to melt the butter in your pocket. XD I've never been a fan of the potbelly, though, which is why I never draw it.
Aaaaanyway... about this pic. Initially I wanted to go for some element of angst, so I chose to make use of Bob’s supposed congenital heart defect, as mentioned in the episode “Funeral For a Fiend” (season 19, episode 8). Hard to say whether his heart problem is canon or not, since he faked cardiac arrest in that episode, and I don’t believe it has ever been mentioned again before or since.
Here Bob and Cecil are reenacting a murder scene from one of Shakespeare’s plays, and Bob, rather than admit that he’s confused a line from “Hamlet” with “Julius Caesar,” has decided that the nobler thing to do is fake a heart attack. As melodramatic as he normally is, I can easily see him working himself up into an actual cardiac episode while acting out some over-glorified death scene.