1988 Buick Century - Hand-me-down from my sister, used to be my grandmother's car. My sister rear ended someone with it before I got it, and had pushed the radiator into the block. The thing ate oil + antifreeze like you wouldn't imagine. It finally degraded to the point that it couldn't be driven anymore.
1989 Dodge Shadow - Only had this one for about 3 months - I made a left turn on yellow and got T-Boned by someone in a hurry
2001 Oldsmobile Alero - Had this thing on a lease and turned it in at the end.
2003 Pontiac Vibe - Got this after the trade in, also on a lease (bad decision). I was driving this back and forth from Chicago to Indiana every week when I was in college, and racked up way too many miles on it. About 9 months ago, I had to buy out the lease at the end because of the mileage. A week ago, the thing developed a rod knock... so it was shot. Traded it in (and got raped for being so upside down)
1953 Ford Mainline - This one I picked up from my wife's old landlord. She was living in the city, and the landlord could not drive it anymore due to a back injury. Anyways, it was eating up one of his garage spaces (~$200/month if he rented it), so he wanted to get rid of it. I had just bought the house, so I was really short on cash, but I offered him $300 for it and he took it (mostly because I promised him I wouldn't chop it). The thing needs a little work, but it runs. I will be restoring it as time and money permit. Will be a fun drive-in car for the summers (hopefully this summer!).
2006 Ford Mustang - Well, I figured if I was going to get a new car, I was gonna be screwed anyways from the trade in... so I might as well have fun while I was doing it. If not for the vibe, I could have gotten the GT... but as it sits I only got the v6. Still the best car I have owned (by far).