It's always interesting to see how Jewish artists in different times and places depicted the four sons of the haggadah. In Chicago, 1939, for instance, the Wicked Son was drawn as a wearing a black suit with a cigarette in his hand [Aside: why are the candlesticks positioned on chairs?]
In Prague, 1526, the wicked son is given a martial costume, and a feather plumed hat, and in the Prato Haggadah (13th century Spain) he wears a sword and a dagger and points an accusatory finger. The Wise Son look something like a monk. [Aside: If this is a Spanish Haggadah, why is the Yishtabach at the end of Halel written according to the ashkenazic rite?]
And what about in the yet to be written blogosphere haggadah? Sure, traditionalists will want Gil for Wise Son, and Mis-nagid for Wicked Son, but in my own book we'll use AddeRabbi and TobyKatz. For lovers of irony, GH is the Son Who Does Not Know How to Ask, and my favorite Simple Son will always be Holy Hyrax. Any other ideas?