To be on this list the book must satisfy the following conditions:
- It doesn't require an enormous amount of background material to understand.
- It must be a fun book, either in recreational math (or something close to) or in philosophy of math.
Here are my two contributions to the list:
- What is Mathematics? Courant and Robbins.
- Proofs that Really Count. Benjamin and Quinn.
So, my favorite recreational math book growing up was Mathematical Mysteries, by Calvin Clawson. It's light on rigor, but it contains a lot of interesting mathematical concepts.
Also, I think it's important to list Herbert Robbins as an author when talking about What is Mathematics?, seeing how he was the one doing the actual writing.