Drove parents cars until graduating college in 1986. I paid for college, they let me drive one of their cars. (Pontiac Safari Station Wagon, Chrysler Cordoba, Pontiac Phoenix, '80 Toyota Celica Supra.) I think it was a good deal.

'80 Toyota Celica Supra - bought from Dad when I graduated
'76 Chrysler Cordoba - bought from Dad when I got married, needed 2nd car (6-8 mpg, good thing I lived close to work)
'85 Toyota Celica Supra - Super Dark Red - best car I've owned
'90 Ford Explorer - 1st new car (for wife) - kids on the way
'94 Ford Explorer - 2nd new car (for wife) - a little nicer than the 1st one
'93 Pontiac Bonneville SSEi - 3 kids don't fit in a Supra but I should have kept it (the Supra) around for fun.
'00 Dodge Grand Caravan - 3 kids and a dog going on vacation don't fit in Explorer
'85 Toyota Celica Supra - Black this time, sick of driving big cars
'06 Toyota Highlander - 3rd new car (for wife) (anybody see a pattern?)
'97 Toyota Camry - from inlaws for kids to drive
'05 Chrysler Crossfire SRT-6 Roadster - replaced Black Supra that was turning into a money pit.

Bikes
'82 Yamaha Seca 400 (brand new out of the crate in '86)
'84 Honda Nighthawk S
'85 Honda V65 Sabre
'88 Kawasaki Concours
'99 Honda ST1100