My first car was a Triumph TR3, got it when I was 16, paid $200.00 for it. It actually looked a lot like this one.
http://www.rmauctions.com/images/cars/az09/AZ09_r131_01.jpg
What a blast driving on those curvy West Virigina roads. The Lucas electronics sucked, and sometimes the lights would all just shut off, usually in a dark and dangerous stretch of road. Starting it up was an adventure every day, often required priming the carbs, a push, and popping the clutch in 2nd gear, and maybe just the right amount of choke.
But it always started and ran fine once it was running. Only 2 seats, but I took as many as 5 friends with me a lot of times. It took us everywhere we wanted to go. With those low doors, you could reach out and touch the road if you wanted, and man, was it good on the curves. When you went 70, you knew that, by God, you were doing 70!
I think every guy should have a car when he's young that forces him to work on it a bit so he can learn at least enough about cars to keep it going. There's something you can use for the rest of your life, unlike, say, calculus.