16 books · Ages 7–12 · Graphic Novels, Chapter Books
Jeff Kinney's journal-format series has sold over 275 million copies because Greg Heffley is the kid nobody wants to admit they recognize. The humor is in the gap between how Greg sees himself and how the world sees him, and that gap never closes. Nineteen books, a do-it-yourself journal, and a universe that keeps expanding because middle school never stops being awkward.

Start at the beginning: Diary of a Wimpy Kid
This is a sequential series — each book builds on the last. Start with book 1.