Jamie is a mordant portraitist - check out this all-too-revealing take on Andy Warhol:
But I am partial to Carolyn Wyeth, although it's hard finding her work. American Heritage magazine did an article on the Wyeth clan that featured several of her paintings, and they are arresting (and strange).
I think Winslow Homer may be my favorite American painter, though.
Way in the background, under the wing of the duck on the left, you can see the guy in the boat firing his shotgun toward the ducks (and the viewer).