They have to be able to reach high enough to get some of it. It has to repay their time in high school. It should also show them there's more to reach for, but they need to be able to get some of it.
For me, Gatsby was... not entirely terrible. It was mostly a waste of my time, but looking back I can see some of the themes were at least somewhat worthwhile.
Portrait of the Artist as a Young Man was an absolute waste of my time. If Joyce is worth an adult reading (which I doubt to this day), then don't make high school kids read him.