On the other hand, don't neglect the classics because you think they're played out. I think someone influential made a snide comment to me when I was young about how overrated and irrelevant Dickens and Shakespeare are, so I didn't read them until after college, at which point I discovered how misguided I had been. But yes, definitely, there is great literature from the 90s, 00s, and 10s that young people are often not exposed to!
I think they're overrated - for teens. I know why we inflict them on kids, but they're hard to appreciate until you're an adult.
I know a super-smart fourteen year old. He tells me The Hunger Games and Harry Potter are the best books he's read.
When I was in my teens I was reading:
Herman Hesse
Thomas Mann
John Barth (which shows how old I am...)
John Irving
John Updike
Doris Lessing
A lot of SF, classic/mainstream and otherwise
Literal piles of electronic and computer hobby mags
OMNI magazine
Articles in Encyclopedia Britannica about tensor analysis and simultaneity which I totally failed to understand
A buy-weekly-and-keep popular subscription encyclopedia I talked my parents into getting for me.
Of those, OMNI made the biggest impression because it hit an art/science/futurism sweet spot that I haven't seen copied since. (Mondo 2000 was on a different moon of the same planet. Wired is a very poor imitation.)
The buy-weekly encyclopedia was unexpectedly useful too, because it covered things like art history and politics I'd never have thought about otherwise.
I think 14 is as much about curiosity, creativity and emotions as raw intellect. So if you're just creating a reading list about stuff to think about in a clever way, you're going to be missing a lot of potential for more rounded development.
I'd think about experiences as well as books. Go to sports. Go to an opera. Go to art galleries. Go see bands. Travel and have adventures. Go to a political debate. Go see some classical Greek tragedy or comedy. Couch surf with strangers and take the kid along. Go hiking a long way from the Internet. Teach some survival skills.
If the 14 yo doesn't want to have the fam along, offer free tickets and travel for them and friends. (Not so much for the travel...)
And so on. Leave the compiler theory books for later.
I agree with your entire comment except the very first sentence. I think all the stuff you mention is fantastic for 14-year-olds – Harry Potter and (the first) Hunger Games are great and absolutely "new classics" – but so are some of the standard classics. It's true that most people will appreciate them more as adults, but that doesn't make them useless. Of course time is limited, and prioritizing is tough, so maybe some of the experiential stuff you mention is worth prioritizing above old crusty books, but I still think a good mix is a good goal.
