Okay, I get that not all teen boys are trivia nerds.  I was, and so were all my friends, so that might explain part of my bias.  Forgive me for that, but here is the one thing I wished exists back when I was a teen.  Mental Floss.  Started in 2000 at Duke University, it was created as an educational magazine, but fun.  Over the years, it grew into a national publication and featured contributions from such trivia kings as Ken Jennings (best known for winning a whole lot of Jeopardy) and A.J. Jacobs (best known for reading the Encyclopedia Britannica cover to cover). The magazine is now a bit of an empire, with games, T-Shirts, books and a regular trivia blog.  It's those books I'd particularly like to feature.

Mental Floss writers, like the writers at Cracked, rely on humour to make the point.  Historical information is often presented in schools and textbooks as dry, bland dates and names, but here they highlight the oddities and the insane, while still giving the bigger picture of the events.

Two history books, History of the World and History of the United States, cover, obviously, the history of the world and the history of the United States respectively..

Forbidden Knowledge covers more controversial information, facts about crime, drugs, censorship, etc., all sorted by chapter according to the seven deadly sins.  Don't worry, nothing they wouldn't learn in history class.  It's just packaged in a more appealing way.

Be Amazing uses the concept of a self-improvement or how-to books to explain the history of nation-building, x-rays, and pretty much everything else.

A number of smaller books cover more random subjects, including Scatterbrained, What's the Diffrence, Cocktail Party Cheat Sheet.and Genius Instruction Manual, all offering condensed stories of significant cultural and historical people and events.

Because most of the books are bite-sized or at least feature chapters that aren't connected, this is great for quick reading or for short sessions, and the fact that they aren't too complicated make them good choices for guys who don't have a lot of patience for longer material, or claim they don't have time to read.