People are often surprised to find out what kind of car I drive. When they do, they look at me like I've just told them I eat BBQ baby flesh (actually it's much better boiled). Strangely enough, I didn't start out as a car guy. In fact, I always kind of hated those guys. They always seemed like they were over compensating.
As it turns out I've kinda turned into one of those guys. These days, my friends are surprised if I can keep a car for longer than a year. It actually started one day when I accompanied a friend of mine looking for a car. He was interested in the 350Zs when they first came out. It must've been something the car salesman slipped into my coffee because ever since I've had a penchant for cars.
Here's a brief history of my cars.

1985 Honda Accord LX (not my actual car, too few dents)
This was my first car. I got it the day I turned 16. If I recall right it had about 80k miles when I got it and power everything. Over the next six years I put over a 100k miles on that car. As Hondas are prone, it was nice good reliable transportation. With a little work here and there it held up nicely till near the end which lead to my next car.

1999 Saturn SL1 (again, not actual car but same color)
I got this car for 3 reasons: 1) I started looking for new cars because I could tell the Honda was on it's last legs. Good thing the Saturn dealership was at the bototm of a hill. I litterally had to coast the Honda in. 2) I was taken in by the advertised sales experience. At that time, buying a Saturn was unlike buying any other car. In fact, it was akin to buying pretty much everything else in this country. There was a listed price. You paid the price. You took your product home. There was no concept of sales jousting. To this day, I absolutely dread dealing with car salesmen. In fact I was just at a Ford dealership and even Vince Neil doesn't reek of that much desperation these days. 3) It had PLASTIC DOORS!! Great for someone whose previous car had tons of dents.
This was also my first brand new car. I remember distinctly asking the car salesman if I had to let the car idle for 15 minutes in the morning before I could drive it. The only disappointing thing I remember about it was that they didn't take my picture and put it on the wall as they did for all the other customers. I showed them when they tried to start the trade in they just got!

2002 Toyota Prius (Not actual car but actual MOON BLUE color, not to be confused with Purple)
Not really sure how I ended up with this car. Being a bit of a gadget otaku I went into the dealership to find out more about this new "hybrid" technology. Next thing I know I'm signing paper work for what appears to be a visually purple car, but the salesman is constantly reminding me that it's "moon blue". In any case, it was a fun car. Not much in terms of performance, but filling up once every month was fun. There's also this game that all Prius owners play in which they try to maximize their MPGs. For example, driving just slow enough so the mechanical engine never kicks in. I once got it up to 75mpg. That was a great day. Yet it was still purple which lead to the next car.

1969 Mercedes 280SL
It was about this time that I had gotten bit by the car bug, that and I was tired of being told I was driving a purple car. This car had been floating around in the family for years. I traded my Prius to my folks for it. I think most people thought that I'd get rid of it once summer past. I kept it for the next year. This thing was work of art. It had a wood dash, over sized steering wheel, and the sound of the engine was amazing. Alas, like 40 year old cars are prone things starting to go wrong with it and finding parts was becoming difficult. That and finding a gas station that sold leaded fuel too. Which lead to the next car.

1955 Porsche Speedster Replica (2003 actual)
At the time this seemed like the ideal solution to my 280SL blues. It had the classic stylings of a vintage car, but he reliability of something that was built the last year. Alas, I drove this thing for a week before I realized that these cars were truely built for the Southern California weather. With the top up the cars visibility was similar to that of being inside a WW2 Sherman tank. On top of that, being a true speedster it didn't really have side windows like we think of them today. They were more of translucent cut aways that sat on the door edge.
Luckily, with the help of my Dad, I was able to actually return the car to the dealership (a first I'm sure) which then lead to the next car.

2001 Audi TT Quatro
This car was the next logical step. It had the styling queues of the Speedster (much more so than the Boxster) but the reliability (and visibility) of a modern car as well as the performance. This thing ran like it was on rails. On top of that it could handle adverse weather like a Hummer. I drove it all the way back and fourth between Seattle and Sun Valley without any problems (except the cop nailing me doing 100 in a 50 zone). It had seat warmers too. Girls love seat warmers. The stock stereo was strangely really good too.. Days like today in Seattle I really miss this car.
Which leads us to my current car.

2005 Ford Mustang GT
Not sure how I got hooked on this car. Probably saw a commercial or saw one on the street. In any case, I slowly became obsessed with the new Mustang design and all things Mustang. I waffled for the next year on whether I should get one or not. By chance, I ran across a guy that had one for less than a year and had done much of the work to it that I was planning on doing. I pulled the trigger. It's a very different car than it's predecessor, but equally fun. It doesn't handle anywhere near as well, but 350 rear driven horse power off the line is a different kind of fun. In addition, there is nothing like the throaty sound of this car speeding up the freeway ramp. I think one of the reasons that I've kep this car so long is the many modifications I've put into it. I'm sure it can do the Kessel Run now in less than 13 par secs.
So that's my car history. I think people are the most surprised by what I'm currently driving. I still can't get a straight answer what people expected me to be driving (perhaps something more Moon Blue).
What are you driving? What do you think your car says about you?