We'll start with the senior year ride. And since I grew up in NYC, I'm talking about college, not high school!
1) 1990 (?) Civic Wagon. I didn't actually own this car, but I claim ownership since I was the one who sent it to its demise. Originally owned by my brother-in-law, who sold it to my brother, who let me drive it to/from school. I moved out of college in this car, and got into the first accident on Broadway. Second accident was in Chicago, which sent Grandma to the hospital (God bless her, she was a strong woman) and cut our cross-country trip short. Don't know how we limped back home to NYC, but we did. Then I think the car was junked. I think this is how the wagon obsession started.
2) 1991 (?) Infiniti G20 sedan. I can't believe I forgot the model year! I know it was an early model since the 1993.5 got the high-port (or is it low port?) version of the venerable SR20DE engine. I also know it was a '91 or '92 since I had the dreaded 5th gear pop-out! I remember getting a heavy-ass package from UPS with my new transmission in it. It came from a G20t model, so it had the factory LSD, though I don't think I put it to good use because I was just a punk ass kid street racing bum at the time. I also remember my Greddy exhaust which I thought sounded great. I think this car is still sitting around the parent's farm somewhere.
3) 2000 MR2 Spyder. Moved to Cali so I had to get a convertible. It was the peak of the dot-com boom and we all thought we were living the good life. Well, I did for a few months before my company closed and I was making car payments with unemployment checks. Great car though, glad I was able to keep it for so long. I didn't put the top down as much as I should have. This car got my started with real driving, i.e. autocrossing, twisty road rallies and open track days! I sold it to a nice woman at Stanford medical school, and I still look around for another one considering how cheap they are.
During my MR2 ownership I went through a bit of a Nissan fanboy phase. Kids were just starting this "drifting" thing and 240sx's weren't completely ridiculously overpriced just yet. I may have helped contribute to their price inflation...
4) Smashatch - that's the name for the first 240sx I bought. A tree had fallen on the hatch and it was completely fubar'ed. Of course, I thought I could just take a Sawzall to it and make myself an El Camino. I was wrong. Living in an apartment with no parking didn't help. I sold it for 3x the price.
5) Creamy - yellow and grey two-tone coupe. I thought it was hot shit, but it probably was just shit to everyone else on the road. It had a working HUD which was nuts for 1991 in-car technology. Cleaned it up a bit, removed some tacky vinyl and drove it around for a bit. Replaced 3 of 4 fuel injectors so there wouldn't be gas spurting all over the hot engine. Sold it for more than twice what I paid.
6) OneLiner - black 240sx coupe with R32 Skyline taillights and the almighty SR20DET! The name is a play on the Japanese name for the 240sx hatchback (180sx) and the Coupe body with GT-R lights. Most people would call it a OneVia (for Silvia), but I had to be different. This car was awesome! Super light chassis, craptastic tires and stout power from an otherwise stock SR. Probably only 200hp, but it felt like a lot more. I even went to the track once, and despite the plastic-fantastic big-wheel like traction afforded by $100 tires (meaning $100 for ALL FOUR), I had lots of fun. My buddy called it the "Beater Battle" since he brought out his 'other MR2' to have some fun. I sold this one for a tidy profit as well. I would still get another one.
7) 2004 WRX wagon - this was the "family car" to replace the Spyder. It was still a compact sports car, but with rear seats that could (barely) fit a baby seat. Had the works done to it, but unfortunately I never got to track the beast. Went to a Subie rally once, but everyone was just sitting around. I took her up Mt. Hamilton myself and boy was that fun! Brembos were amazing, Stage 4 upgrades on the EJ20 was ridiculous. It still oversteered a bit, but you could just manhandle the car and it would do no wrong. Didn't help me improve as a driver, but it was an awesome car. Sold it to a good friend of mine at work, so I know she's in good hands.
8) 2008 VW Passat wagon - yup, another wagon. This was the first German car and we got it at a very good price. I wanted an STI wagon, but it wasn't any bigger than my WRX. The new A4 Avant is nice too, but about $10k too much. And it felt slower than the Passat, which has the same motor, but doesn't carry the weight penalty of AWD. It's a family wagon, FWD is fine. I'm actually surprised by how much I like this car. I don't think I would ever "love" it, but it's a dman fine vehicle. The small details in design and functionality really make you appreciate good engineering. I expect to drive this one for a long while, at least until the kids are out of school (elementary, not high).
That's the list! I'm actually disappointed that it's only 8 and not 10. I could count the G35, but I always think of it as the wife's car. If it were mine I would have modified something (anything!) a long time ago.