Inspired by this Doc Searls post listing all the cars he has owned.
81989 Plymouth Laser* - The twin to the Mitsubishi Eclipse. I bought this upon graduating from college in 89 and getting my first real job. By all accounts it should have been a solid car. I apparently bought one that went down the assembly line the day before a long weekend, or maybe on the first day of hunting season. It was a lemon with electrical gremlins that I never did figure out. I had to make sure I always parked it pointing downhill, or at least on a flat surface as it frequently needed to be push started. The real advantage of it though was that the back seat was only useful to midgets, so it was functionally a two seater and kept me from having driving duties back in my bar hopping in Buckhead days.
1991 and 1992 Mazda Protege - My wife had a 91 Protege, and I was so impressed with it that I dumped the Laser and bought one myself. It was the base model with a stick shift. It was a great car that gave me no troubles at all. She had the luxury version with power moon roof, power windows and all that.
1996 Isuzu Rodeo - With the arrival of a child in 1994 we quickly realized that life as a two sub-compact family was less than convenient. When we bought the Rodeo I traded in my Mazda and took Michelle's 91 Protege as my daily driver. The Rodeo was a great vehicle. We had no problems with it for 4 years.
1997 Mazda 626 - Right after Y2K the transmission stated to act up in the 91 Protege. Since I had already rebuilt the transmission once about 3 years previous, this seemed like a good time to bail. 150K miles out of a 4 cylinder engine is nothing to be ashamed of. I replaced it with a 97 Mazda 626 with 36K miles on it. I'm still driving the 626. It just passed 120K a few weeks ago. I plan to get at least 150K out it, hopefully more.
2001 Mazda MPV - As a two child family we found the constant lifting toddlers up and down into an SUV to be a royal PITA. In early 2000 we went to the DC Auto Show for a day out and found the MPV there. We wanted the fold down seats of the Honda minivan but didn't have Honda money. The MPV provided a lot of the same features for far less. Reviewers always claimed that V6 engine was under powered but it never bothered us. It's a freaking minivan! I don't think it ever saw a shop for anything other than routine maintenance.
2005 Dodge Durango - With the addition of a horse to the family, we needed something capable of pulling a horse trailer. The MPV obviously wasn't going to do it. I considered keeping the minivan and getting a beater truck for a tow vehicle, but the wife vetoed that plan. I'm still not convinced that we made the best financial decision, but having a HEMI under the hood certainly can be a lot of fun. The truck was coming off a one year corporate lease, and I got it for about 50% of the list on a new truck. It's the most loaded vehicle we've ever owned. It has every single option available on a 2005 Durango. The HEMI is amazing. Towing 4000 lbs of horse and trailer at 60 mph the RPMs are comfortably under 2000. Unfortunately the mileage when towing is not-so comfortably under 10 mph.