Before critiquing the art, I will start with the title and remark that it certainly is catchy. Much surrealism is also dark art but because the sur-real emerged as art that was to explore the subconscious depths of the human mind, some surreal art must of necessity partake of the humorous. The ability of the brain to see and to appreciate incongruity is deeply hard-wired in us. "George Squashington" does fall squarely into the "humorously-surreal" classification. The wig combined with the texture of the squash suggests the otherwise non-existent link between the Father of Our Country and one of the vegetables he (actually his slaves) grew at Mount Vernon. Adding to the surreality are the clouds with their false bottoms. Realistic clouds would have subtracted from the mood. The cherries to the right and the stump to the left contribute to the fine compositional elements of this work.
Had not seen this piece before. Was caught by surprise; laughed so hard, I had a coughing fit! Who could possibly even think of such a piece (George Squashington!). You have one heck of a creative comedic mind.