Used car for 16 year old son.

[spareparts]

I agree on the Cherokee, mine has held up well under my right foot. Just make sure to get 2 wheel drive so he won't feel like he needs to get mud on the tires.

[tsubaki]

Cherokee, he's gonna tear it up but at least you can work on it and have a chance of repairing it.
Definitely the 4.0 engine.

[CaptJ]

I like the idea of a car he can work on/has to work on. Teaches him to repect what he owns and drives. Naturally he must have the desire to wrench but it should come. My dad bought me my first car when I was fourteen 1980 from a boneyard and my '68 camaro convertible was my baby. Even with the plywood floorboards.
Civics, Corollas, Altimas are great cars and easy for him to do the brakes, oil changes...maintenance.
A little two seat pickup truck like a reg cab ranger may helppost pone you from becoming a grandfather for a little bit.
Lots out there right now good luck