My dad hated reading Baum for whatever reason. We liked them.
That was going to be my suggestion. My sure you get illustrated editions.
The Mary Poppins series was a favorite for both me and Celtling. Also Charlie and the Chocolate Factory and the sequel which escapes me.
The Boxcar children
Encyclopedia Brown
The How to Train Your Dragon series
The Junie B. Jones series is hilarious. http://juniebjones.com/
I second the recommendation of The Phantom Tollbooth. It’s still my favorite book.
The Homer Price books (H.P. and Centerburg Tales) by Robert McCloskey. Everyday life in postwar small-town America. Usually realistic, but there are a few times the laws of science were broken in the name of a good story. If you want a preview the doughnut machine chapter was adapted into a short film viewable on YouTube here.
I was going to say that. I was in charge of lunch with the five-year-olds at a preschool, and we read some Oz books. They were enraptured. I know I read them up until about the age of ten or 11, and still loved them.
Beverly Cleary is not too young for the 8-year-old. My 3rd grade teacher read Ramona the Pest to us in class, and we loved it. It’s about a kindergartner, so you wouldn’t think at first blush third graders would like it, but it has universal kid-appeal. Some of the “Girl best friends” Beverly Cleary books might not appeal to the 5-year-old, like the Ellen Tebbits books, but the Ramona books have much universal appeal, and so do the Henry Huggins ones. Also the one-off Mitch and Amy.
Other books I read as a kid that might still have appeal for children today, and might also hit both the ages you are looking at, are the Alvin Fernald books.
Modern books I am up on are mostly for kids a little older-- things my son read recently. But FWIW, when my son was younger, he also did like Alvin Fernald, the 3 Investigators, the Witch books, by Ruth Chew, No Flying in the House, The Teddy Bear Habit, and much of the stuff already mentioned, all books from my childhood. He also kind of liked Freaky Friday, but I think it’s more of a girl’s book.
Charlie and the Chocolate Factory is another good one. It was read to me in the first grade, and I read it to my son when he was five. I think it would still interest an 8-year-old.
Ivy and Bean! Plenty of pictures, freakin hilarious, very much in the Beverly Cleary tradition.
Ooh, the Alfred Hitchcock and the Three Investigators books were favorites of mine.
I remember those, and liked them at the time.
I’d recommend an illustrated The Hobbit by J.R.R. Tolkien, or an illustrated Sherlock Holmes collection. My fifth-grade teacher read Holmes stories to the class during rest period, and we were enrapt.
The boy is only five! I think a lot of these recommendations are great books, but way too old for him.
I love them! Should read them next.
I’m reading the third Sideways Stories From Wayside School book to my daughter. She’s 7 and understands all of it. I love how Louis Sachar added all kinds of fun things like a chapter that is backwards, or how reading them in order adds bits and pieces. The chapters are only about 5 minutes long but they’re each a story so you don’t need to keep going when you finish one.
Like I say, it really depends on the kid. My younger girl is a little more persnickety about what we read to her, but my older girl was up for anything, whether or not she could understand it. I read her The Wind in the Willows when she was three, and although I’m sure he understood less than half of what was going on, she was enraptured.
For a five year old, I’d say Ramona and Beezus and its sequels will be perfect. Has a great older sibling/younger sibling dynamic that your crowd will recognize. Similarly, Judy Blume’s Tales of a Fourth-Grade Nothing/Superfudge books. Warning: in Superfudge, there’s a chapter about Santa Claus not being real, so don’t walk into that unexpectedly.
Ages 8 & 5. Tell you what, this worked for me and my brother at those ages, and it worked for my kids. It turned me on to a lifetime of loving fairy tales & short stories, and same with my kids.
These are NOT Disney or Grimm whitewash platitude stories, NOR are they the ultra-dark pre Grimm tales out of Gaul (where the wolf slaughters granny and serves her up to Little Red as lunchmeat and wine before devouring the child as well). Nevertheless, they are enthralling tales with very real suspense and sometimes quite terrifying for especially small kids (but not so bad you’ll damage the kids). They use a fair amount of old-fashioned vocabulary and syntax which is useful for parsing some of your Romantic & Victorian era literature when they get there, simple enough for your 8 year old to read, and short enough to not exhaust anyone.
This one is also a really good collection. It’s Italian, so there is quite a bit of Catholic imagery that might perplex small non-Catholic kids. But once you get into it you start to notice some of the stories are similar, as though incorporating fragments of ones you’ve already read. Collectively, the stories form a sort of moral and (fairy tale) historical tapestry that ties them all together. Less frightening than the English tales, but still very entertaining.
Could be a bit young for the 8 year old, but maybe Uncle Wiggily.
They are pretty short so it’s easy to fit in a chapter or two or three depending on the amount of time. There is a little bit of sexist theme, like “boys do this” or “girls are like that” kind of stuff, but pretty easy to see it coming and change the language if desired.
My kids loved those. And each story ends with something like, if the monkey doesn’t drop his hat in the wishing well, and get his pants wet getting it out, next time I’ll tell you about Uncle Wiggily and the Choo-choo Train. That was one of the best parts.