Great idea Ron. Okay, I will give this a try. My pictures attached are not my real cars but rather pictures from the web. I will even admit to one car that I wish I never bought - can you guess the one car that was embarrassing to own?
I was also born 1955.
First car at 15: 1962 Ford Fairlane 500 4 door 260 V8 that I thought was fast. Low mileage car (42K) for $200. I sold this car because I had a line on a 1967 ford fairlane GTA 390 four speed car for $600. It turns out the guy still owed $900 and the car was repossed. 
My car had light green bottom and white top.
Second car was at 17 years old. It was a more-door 1965 Chevy Bel Air with a 283 double camel hump heads with a three speed manual on the floor for $300!
This car was fast and earned me my first and only wreckless driving ticket. I was caught power shifting on graduation day in front of school. I later beat that ticket in court (cop did not show for hearing). Car was stolen/stripped within 6 months of buying her. Wheels, tires, carb, and all my tools from the trunk were stolen. My friends did a valve job on her in training school and screwed up the valve guides - car smoked horrible after that valve job, then one day had a carb fire and wrecked the wiring - i had enough - got $40 for scrap. 
My car was black with chrome reverse wheels.
Third car was bought new when I turned 18 and needed a good gas mileage car for trvelling to work - 1974 Ford Pinto
I drove this car 1 year and put 18,000 miles on her. Then I was disabled in August 1974 and could no longer drive a manual transmission car. I held this car until August 1975 when I traded her in.
My car was mettalic green.
Fourth car was bought in August 1975 - a 1975 Ford Elite. I had hand controls installedand drove this car until 1993 with 125,000 miles and no significant problems ever. My best car ever! 
My car was light blue with dark blue padded top.
Fifth car was bought in 1993 and was a garage kept original 1976 Thunderbird with 20,000 miles. This car still had the original tires. I paid $6,000 for her. It had the 460 cubic inch beast. I had the carb rebuilt, hand controls installed but could not ever transfer in and out easily as I could in the Elite. It was at this time I got an offer to buy a van with low mileage (900 miles) already equipped for a disabled driver. So I sold the car to my Barber’s brother in Germany for $7,500 and he paid the $750 shipping fees.
My car was white with red paaded 1/2 roof.
Besides my 1993 ford van that was driven until 2004, I bought a 2002 Ford van already equipped for a disabled driver (1,000 miles) in 2004 off ebay from Michigan - which I drive today.
The only other old car I bought was in 1989 - 1964 Chevrolet Impala SS convertible for $3,500 and invested another $7,000 in her up to 1994 when I sold her at carlisle for $11,000 to buy the 1993 ford van. This was a great car 283 two barrel, two speed auto with torquoise body, white top, and white and aqua interior - put together all original.
My car was torquoise, white top, white and aqua interior.
Now you know my history of cars - of course my wife has had many cars as well - but that is another story.
Curt