After raising two kids through college, I will say the very first car needs to be a cheap, beater. You don't want to keep full coverage with a 16 year old, in a Jeep. Both of mine have totaled a car before they were 18. They were accidents, nothing stupid was being done, but the vehicles were still toast. Make him earn the Jeep. 12 months with no accidents or tickets in a beater, then he gets something else. If he doesn't have to earn it, he won't respect it. If he doesn't respect it, it will end badly. If you don't decide to do that now, you may be deciding after a couple of destroyed vehicles.
If it isn't earned, it has no perceived value. Earning something gives it worth. If you get him something else, to start, and he pitches a fit about it, tell him that you will match whatever he has saved up so he can buy something on his own. Unless he is completely an idiot, he will say thanks.
A buddy of mine called me when his son had pretty much destroyed a civic by driving it where it shouldn't be driven. Mostly cosmetic damage, but a lot of it. He asked me if I thought it was a good idea to give the kid his old Titan. WTF? No it isn't a good idea. Make him drive the Civic in the condition that he made it. You don't reward bad decisions. You don't break something through misuse and get a better thing to replace it with.
Full disclosure here, my daughter had three cars replaced in two years before we came to the conclusion that we were rewarding bad behavior. She took the last one to a body shop without telling us about the single car accident. The body shop called us because the vehicle was in my wife's name. We paid the repair bill, put the car on Craigslist, and sold it before she knew it was out of the body shop. She went without a car for over a year and we didn't help her get another one until she straightened up, got her GED, and enrolled in college. She is in her third year of college and she is still driving the 2003 Forrester with a salvage title that we let her drive. She is happy to have it, no matter how bad it looks.