My car history started with a 1990 Dodge colt.

My dad bought it for me and my brother in the summer of 1998 for the princely sum of $2500. It was awful. He bought it off of a guy who took two ruined cars and made one seemingly OK car out of them. Only the wiring harness looked like it was put together by gibbons, and the car shorted it self into a stall every time it went over a bump.
The fuel gauge showed 1/4 tank, no mater the actual level, and eventually the transmission stopped going in reverse. We sold the car to a friend with a garage for about a grand after a winter of me being stranded constantly.
My next car was a Mazda 1987 RX-7 which I bought with the remaining cash from the Colt, and some of my own money. My dad said I was a idiot, and was soon proven correct.

The car blew an apex seal after six months. It taught me how to drive stick though, and to this day it is the car I have been the fastest in (212km/h), so it holds a special place in my heart.
I drove it on one seal down to the local Mazda dealership and made a straight trade for a 1983 RX-7.

It was wonderful. Light and nippy, and I thought I looked really cool in it. This car gave me a sense of freedom I haven't been able to replicate yet.
It ran almost faultlessly for two years until the summer of 2001, when, after returning from the Canadian GP (and starved of my "cool car" in a city of amazing machinery) I promptly blew an apex seal in the engine when I missed fourth and hit second on an enthusiastic down shift.
I bought a parts car, stole the engine out of it and helped a local garage owner install the new engine in my pride and joy.
Two years later, while returning from a stint as a guide in the mountains the car's suspension collapsed...probably from rust. I still had the chassis of the parts car, and started the task of moving the working bits from my daily driver into the parts car, a job I would never complete.
To get me around while I re-built the parts car I bought a 2000 Honda Civic DX special edition hatchback.

It was reliable as all that, and had a nice, subtle spoiler, in addition to the Acura Integra alloy wheels which came with the DX special edition (apparently built to celebrate the final hatchback Honda would bring to NA...aside from the SiR.
While I was secure in the knowledge that the car was never going to leave me stranded I got really bored with the car really quickly. I was pressured into buying it by my dad...and it was an automatic. I missed driving a manual something fierce. I started to drive the car faster and faster, trying to make it more engaging. The day I was chased by the police, after taking a corner way too fast was the day I decided I needed to do something about it.
I was awarded some stock when the family business was sold in 1998 and went public, and after holding on to it for five years (as all the family had to do according to our selling agreement) I sold a good chunk of it. I wanted a more interesting car, and was once again pressured into buying something I really didn't want.

The car was comfortable, and I still think it was good looking, but it was almost as boring as the Civic. I didn't drive it very often, and sold it a few years after.
In 2005 I got rid of the Civic, replacing it with my current car, a 2001 Legacy.

It's not glamorous, but I have had it for four and a bit years now, and am still not bored. It can fit lots of stuff, handles reasonably well, and the AWD system makes me feel like a driving god in winter.
Hands down best car I have ever owned.
I also owned a Chevrolet Suburban for a long time, it hauled the RX-7s around a few times a year, but mostly lived at a friends house in the country, until it was stolen, never to be heard from again.

There was also a 1983 Mazda GLC I drove around for a month...since I decided I didn't want to drive the RX-7s in winter anymore. Eventually the brakes broke, and they were going to cost more than the entire car was worth to fix. I loved that car for the month I owned it...cars with really short wheelbases are wonderful.
I sold it to the guy who told me the brakes were shot...I think he turned it into an ice racer.