I needed a car for high school and my parents gave me a budget and said "go pick something out, let us look it over and if it looks good we'll pay for it but then it's your responsibility."
1976 Buick Le Sabre Custom sedan - this was 1985, I was a Junior in HS, the car was pretty much perfect, it had 80k miles, a 350V8, loaded, owned it for one week b/c I totaled it, 100% my fault.
1970 Chevrolet Caprice Classic sedan - this replaced the Buick and while it was clean, rust free, etc, it was an awful car. It had a SB 400, God only knows how many miles (I would say it rolled over twice because everything was worn out on it.) When I went off to college my parents offered it to me, I turned it down because I couldn't afford to keep it on the road, it was constantly breaking down. It looked pretty sharp, it was a North Carolina car, but it was pretty well worn out.
The rest are cars I purchased and owned :
1992 - new 1992 Saturn SL2 5-speed manual, blue/black with light grey interior, I purchased this new from Saturn b/c GM financing was a then amazing 6.9%, I wanted a Honda Accord coupe, Honda financing was 14% - I had the car for 18 months - someone hit me on the way in to work and it was totaled.
1993 - 1993 Ford Probe GT V6 5-speed manual, black w/red interior, pretty well loaded. I put 3 exhaust systems on this car, it was constantly in the shop, fun car when it wasn't at the Ford dealership but after a few years the expense and dealership pain outweighed the fun part.
1998 - 1995 Toyota Avalon XL - gold w/beige leather it had like 25k miles on it - I traded in my Ford Probe and gave Avalon to my wife and then I took her 1991 base Toyota Camry 4 cylinder automatic. Her Camry had 100k miles on it, I put another 120k miles on it.
2002 - 1999 Toyota Camry LE - 4 cylinder, automatic red w/beige cloth - this had like 14k miles on it - I bought this car to replace the '91 Camry, my wife liked this Camry better than the Avalon so then I took over the Avalon.
2003 - new 2003 VW Passat GLS 5-speed manual black w/black leather - another new one I bought - I drove the Avalon for about 6 months, hated driving the Avalon everyday and so I traded it for the VW.
2006 - new 2005 Subaru Outback XT Limited 5-speed - black w/black leather - the VW was rear ended and totaled while I sat at a stop light, I wanted a wagon, Outback fit the bill.
2005 - 1993 Nissan 300ZX 5-speed - blue w/black leather - I had wanted a 300ZX ever since I was in college, I found this one about 100 miles away w/43k miles on it, original owner, so I had it for 7 years and sold it to a friend to make room for the replacement weekender. I put about 5k miles on it, it looked better than when I got when I sold it.
2008 - 2008 Honda Accord EX-L V6 automatic silver w/grey leather for the wifey to replace the '99 Camry - I sold the Camry to a buddy, it had 99k miles on it, he gave it to his son, his son still drives that Camry.
2012 - 2009 C6 Corvette Z-51 6-speed manual w/19k miles, cyber grey metallic over black leather - this replaced the 300ZX.
2015 - new 2016 Subaru WRX Premium black w/black cloth, 6-speed manual - this replaced my Outback which I traded in at the dealership for the WRX. I really loved the Outback but it had around 125k miles on it, it was due for the timing belt/tune up service plus a wheel bearing and I knew it was time to dump a bunch of money into and drive it for 5 more years and hope I was done spending money on it or get rid of it, I chose to get rid of it.