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I don't know where reliability stands on your list, but there are a few cars that I can think of that would make great kid cars for around $20k.
Volkswagen GTI MKV
I have one. It's a fantastic car. A great place for a kid with some money to start. It has all the practicality in the world while having a nice balance of performance that'll allow him to have plenty of fun without getting into too much trouble. The drawback is that reliability is less than stellar. 2007s with 40,000 to 50,000 can be had for $16k plus.
MINI Cooper (S)
These are still popular cars. And they're pretty amazing. It has the practicality of a hatchback and some performance that'll put some great smiles on his face. Definitely a very sweet ride. Plus, chicks dig them.
E46 BMW 3-Series
Definitely a very solid car. They are very nice, quick and drive very well. Only thing is it's a BMW so maintenance will be a little pricey.
Mazda 3
Great little car. You just can't go wrong with one. I think it should be on everybody's list. It has everything you want out of an economy car in a nice, sporty package.
2002-2007 Subaru WRX
The kid-est kid car of them all. It performs well and is pretty decently reliable. It comes both as a sedan and a wagon and both are plenty sporty. There is plenty of aftermarket and community around these things too. Insurance is pretty steep though.
My family bought me (and the family) a $20k car when I got my license. I have similar rules to what the OP is giving his son. The thought of being on my own for everything if I wreck the GTI (or even get a ticket) alone is enough to scare me into doing my best to drive responsibly and safely. As a result, I have yet to have any major trouble in it.
Also, I don't know about most people, but for me, driving a car that the family bought is kinda embarrassing. Between me being shy and the number of kids who would just say "yeah, well I don't get everything handed to me," I don't try to flaunt it that much.
Volkswagen GTI MKV
I have one. It's a fantastic car. A great place for a kid with some money to start. It has all the practicality in the world while having a nice balance of performance that'll allow him to have plenty of fun without getting into too much trouble. The drawback is that reliability is less than stellar. 2007s with 40,000 to 50,000 can be had for $16k plus.
MINI Cooper (S)
These are still popular cars. And they're pretty amazing. It has the practicality of a hatchback and some performance that'll put some great smiles on his face. Definitely a very sweet ride. Plus, chicks dig them.
E46 BMW 3-Series
Definitely a very solid car. They are very nice, quick and drive very well. Only thing is it's a BMW so maintenance will be a little pricey.
Mazda 3
Great little car. You just can't go wrong with one. I think it should be on everybody's list. It has everything you want out of an economy car in a nice, sporty package.
2002-2007 Subaru WRX
The kid-est kid car of them all. It performs well and is pretty decently reliable. It comes both as a sedan and a wagon and both are plenty sporty. There is plenty of aftermarket and community around these things too. Insurance is pretty steep though.
What are you saying? Your family doesn't crash? I think it tells a lot of you that a) you're going to be putting your kid in an 18k sportscar (he's male, he wants something fast I'm sure) and b) "Safety isn't a concern, I've taught him well".
I laugh at the kids whose daddy buys them $20k cars for their sixteenth. Most think it makes them a badass. I know a guy who got a brand new 2006 GTO when he turned sixteen, but he's a rare breed that doesn't have to brag about it. How about you spend $8k on his first car, and when he wrecks it spend the other $10k?
My family bought me (and the family) a $20k car when I got my license. I have similar rules to what the OP is giving his son. The thought of being on my own for everything if I wreck the GTI (or even get a ticket) alone is enough to scare me into doing my best to drive responsibly and safely. As a result, I have yet to have any major trouble in it.
Also, I don't know about most people, but for me, driving a car that the family bought is kinda embarrassing. Between me being shy and the number of kids who would just say "yeah, well I don't get everything handed to me," I don't try to flaunt it that much.