Christina, I pick a few favorites and a few “landmark” type paintings when we study an artist. For example, for Monet I’d pick things like Impression: Sunrise, at least one, maybe more than one of Rouen Cathedral for comparing purposes, and at least one water lily from late in his life, then two more that caught my eye, perhaps. Now there are times that this doesn’t work so well. We did Picasso earlier this year, and I’m not a fan. I just desperately hunted around for things that didn’t have naked women in them. Of course they didn’t really LOOK like naked women, exactly, but still. I only knew two “landmark” ones from him–The Three Musicians, which we covered, and Guernica, which I decided my youngest wasn’t ready for, so we skipped it.
When we have an artist I do not know well, I often get a book from the adult section to skim briefly to get some idea of what is “important” and what is not. Caution: don’t let your kids look at a book from the adult section until you check and see what sorts of paintings are there–I find many that I will *not* be introducing my children to!