First car: 1987 Cutlass Ciera, 4-Door, 2.5L, 4-cyl.
Bald tires, paint comes off when I was it (damn sparkly paint!), driver-side door doesn't open from the inside, no air conditioning, transmission slips BADLY (takes about 30 seconds from 0-55, and that's if I'm lucky), won't go over 55 unless I have at least five miles of continuous running, battery-acid-eaten rear seat, multi-function knob on steering column pops off/missing parts, no fluid in the radiator (leaks out after half an hour), no oil change in two and a half years. However, it does have an awesome 'custom' Rockford/Fosgate symbol spray-painted on the back, and a kick-a$$ sound system that swaps between this and my new car.
Second Car: 1999 Ford ZX2, 2.0L 4-Cyl.
Perfect everything, Kenwood head unit and cd changer, Kicker ZX600 Amp (600 watts), two Rockford XLC 12"'s, Pioneer 6x9's in back, and Pioneer 6 1/2"'s up front. Niiiiice.