Which laptop is best for a 14 y.o boy about to enter high school?

Well it depends on a lot of things. What's your price range? Does he do lots of computer-gaming? Does he plan to do graphic design? Videography? Audio mixing? Is the current computer he uses most a Macintosh or Windows? These are all things that you need to take into consideration when buying a new computer, and if you're thinking of a laptop (which in this case you are), then you need to take into consideration where he's going to use it. I say that as in, will he be using it a lot in bed, or at a desk, or what? It's a good question because some laptops have one big air intake on the bottom, and when used on a bed it suffocates and gets burning hot and sometimes overheats. It's more effective having a big intake on the bottom though, so if it's used primarily on a desk, it's nominal, otherwise there are other ways to go.

I understand this isn't an actual answer, however if you're at a computer store, this is all good information to throw at the person helping you so they can help you choose the best comp.