Anyway- off the bat I would pick:

Henry Rousseau "The Sleeping Gypsy" - I think this might be my most favorite painting ever...

Todd Schorr "The Spectre of Monster Appeal" - I love this painting...it's pretty much the last word in "Lowbrow".
I'm going to have to think over a few more...but I'll keep this idea going. Add your own in the comments- I'd love to know!