A couple months ago, on the cusp of summer, I made the case for reading to your kids—even after they’re past the early grades and reading on their own (or itching for screen time). The column sparked a lot of endearing, interesting notes. Since I try to spend the summer reading actual books rather than education news and indecipherable research reports, I’m in a mood to riff a bit on those exchanges. If that appeals, read on. If not, no worries—I’ll see you next week.

One common query was: What makes for a good family read? There were amusing notes about repeated misfires and beloved books that were a lot worse than parents had remembered. This all resonated with me.

There are books I’ve remembered with great affection that haven’t aged well. Whether it’s me, the kids, or the times, the stories have lost their luster. I remember, as a kid, thinking that Daniel Pinkwater’s Lizard Music was enchanting and mind-blowing. And that was doubly true of Susan Cooper’s Dark Is Rising books, the best bits of which have stuck with me for decades. When we read them as a family, that magic just wasn’t there.

There are books we’ve struggled to finish—like Jules Verne’s Journey to the Center of the Earth, which read like a tedious lecture on Icelandic volcanic formation. And there are wonderful books, like A. A. Milne’s Winnie the Pooh stories, that the boys enjoyed when they were little but have since outgrown.

Anyway, it all got me reflecting on which books we read as a family are likely to land. For what it’s worth, I’ve settled on four guidelines that seem to work for us.

First, I like it when the book is sophisticated enough to prompt questions and discussion. I think it’s a good sign if I feel like my role as the reader is actually necessary, if they’d struggle without me rephrasing things and answering questions. I’m not looking for Tolstoy, but I do want something a little outside their comfort zone.

Second, it can be a good thing if the book is a little overwritten, so long as the plot is clear and the characters are interesting. I’m happy to streamline and update as I go—pruning overwrought scene-setting, tweaking language, and the like. This can expose them to neat stories that they otherwise might not be inclined to pick up.

Third, it helps if the book has a bit of an edge. A little mystery, weirdness, or bad behavior seems to work well for us. That gives us more to talk about, surfaces funny reflections over breakfast or at bedtime, and fuels their interest in what’s going to happen next.

Finally, I prefer when I have a connection to the book. If I’m picking it up cold, reading together doesn’t feel as much like a shared experience. One reason I like reading to my kids is to expose them to old stuff that I loved, think they’ll like, and wouldn’t expect them to discover on their own.

Well, a number of correspondents have asked me if I have any suggestions beyond the familiar tales like the Narnia books, James and the Giant Peach, The Phantom Tollbooth, or Harry Potter—more titles found off the beaten path. The truth is, some of our best experiences are with books that aren’t as widely familiar today.

For what it’s worth, here are five books I heartily recommend. As befits a column called “Old School,” all of them are at least four decades old. So it goes.

The Wonderful Story of Henry Sugar. Roald Dahl’s novella is the story of an entitled layabout who stumbles across a book that changes his life and winds up a mystical Robin Hood. It’s an odd tale, stuffed with British colloquialisms, mysterious powers, gambling, and a backstory set in early 20th-century India. There was a lot of language I translated and more than a little I pruned, but the kids were fascinated and had a million questions about blackjack, orphanages, meditation, and more.

The Westing Game. Ellen Raskin’s brilliant, brisk, convoluted story of a motley crew of would-be heirs trying to claim a fortune by winning a game whose rules are entirely unclear. It’s filled with memorable characters, riddles to sort out, and the whole thing clocks in at under 200 pages. This is a book that benefits greatly from having an adult help make sense of the clues, characters, and what the heck is going on.

The Great Brain. These books are more than a half-century old and are set in Utah in the 1890s. I know, I know. There’s no way you should expect the stories to hold up. But they do. Penned by a little brother about his conniving, fast-talking middle brother who has an eye for cash and a big heart, the tales are surprisingly relatable. At the same time, it’s all set in an era where indoor plumbing is a novelty and a penny is still real money. It’s a frontier world that requires a lot of explanation. There were ultimately seven sequels, several of which are terrific in their own right.

Around the World in Eighty Days. In the late 19th century, laconic British gentleman Phileas Fogg notes that advances in trains and ships have made it theoretically possible to circle the world in 80 days. Betting half his fortune that he can do it, he sets off on a journey full of hijinks, reversals, friendship, and betrayal. I liked it much more when we read it together than when I read it on my own as a kid, largely because chunks of the travelogue are bloated and boring. It’s a neat conceit, but it benefits mightily from being read by someone who can trim the blah blah and make sense of the oddities.

Shoeless Joe. W. P. Kinsella’s offbeat novel is the most surprising title on this list. I wasn’t sure if the kids would be into it, especially because it’s wildly overwritten—with piles of adjectives and painful similes. But that stuff is easy to prune, and the tale itself proved remarkably engrossing. There’s also the occasional curiously placed bit of eroticism, but that was easily trimmed from a tale otherwise well-suited for elementary age kids. Meanwhile, there’s lots of cool history—from the Black Sox scandal of 1919 to the mythos of J. D. Salinger—and a haunting tale of parents, children, yearning, and baseball. Plus, this is the book that gave us Field of Dreams. So there’s that.

If you’ve got thoughts, reflections, or other titles to share, feel free to hit me. This is one conversation of which I never tire.

Frederick Hess is an executive editor of Education Next and the author of the blog “Old School with Rick Hess.”