Wow other people have had a lot of cars too! Thanks for sharing everyone! DSM Rob- Your name fits you well lol. That is a lot of DSMs! To the people with M5s in their teens or early twenties, hat's off to you. That is some boss ****.
Here is my list:
Age 16: Red Ford Bronco II
Age 17: 1988 Cavalier Z24 Convertible Anniversary Edition (My dad still has it!)

Age 18: 2000 Pontiac Trans Am (Intake/Exhaust/Chip ~ 13.3 @ 108 ~ Traded for Corvette)

Age 19: 1999 Corvette Convertible (Stock ~ 13.7 @ 102 ~ crashed then rebuilt and sold)

Age 21: 1999 Jaguar XJR (Factory Supercharged V-8 w/ 370hp/387tq ~ Intake, 13.7 @ 102 ~ Couldn't afford to fix it, so I traded for MS3)

Age 22: 2008 Mazdaspeed3, and a New 2007 Ninja ZX-6R (Stolen after 3 months of ownership, but I'm glad its gone because street bikes are too much for me)
Incase you are wondering how I've got these cars, I worked hard, built good credit, and financed them. And, I do miss the Corvette, and I miss my Trans Am A LOT. Love the MS3 though. Ideally I should have bought another Trans Am to have in addition to my MS3, instead of that stupid Ninja, but live and learn.