The first car I ever drove regularly was my mom's 1986 Chevy Celebrity Eurosport; the radio barely worked and the doors were rusted through; my dad bribed the service guy to pass the inspections every year. After about 6 months of that I moved up to my late grandfather's 1988 Chevy Celebrity; my brother claimed that one and I was left with a wood paneled 1992 Oldsmobile Station Wagon, which my friend lovingly named the Station Wagon of Doom since the shocks were shot and the brakes barely worked by the time 2002 rolled around!
The first car I bought was the 1995 Toyota Corolla in 2004...I was not really sad when it went to my cousin after I bought my first new car (2010 Civic Coupe; still driving it), it was a matter of convenience when I bought it more than anything.