first car - '84 BMW 325e, because I wanted to be different. Only $1500. Was great...when it was running.
Second - '89 Toyota Celica ST. It was a friends' car, we traded. The car was tough, and I kicked the crap out of it. This, above all else, is what sold me on Toyota reliability. Finally sold it at 240,000 miles, after a lifetime of abuse from multiple generations of college students and harsh Midwest winters. It was rusted through all over the place, and had a whole host of other problems, but was still running.
The Celica really was impressive. Great mileage, fairly fun to drive (more so than a Corolla, at least, with about the same mileage), surprising amount of room for hauling stuff (but not much legroom in the back), and reliable beyond anything I've seen. Tons of road trips in that car.