I'm 50.
1st Car at 16:
1980 Pontiac Sunbird
This was my first car. It sat behinds someone's garage for a few years because it didn't run. I bought it for $100. All I had to do is put a new distributor cap on it and put the wires on right and it ran. Only had 60k miles on it. The exhaust rusted out sitting in the snow so I fixed it with a few soup cans. Took out the back seats as mice chewed them up and put two huge speakers and sub back there....lol.
Next car was a 1983 Plymouth Caravelle:
Basically like any of Chrysler's K cars back then. Big piece of shit but was low old lady miles when I got it. I ended up selling to a coworker who got his girlfriend knocked up and they needed a reliable car. I gave them a good deal on it to help them out.
Next was a 1988 Chevy S10 4x4 extended cab Pickup:
This is the car I loved the most in my life. I bought it with about 80k miles on it but it was mint. Had the big 4.3L V6 and it could get up and go pretty good for a little truck. Mine had a some lift added to it compared the one in the picture. It was 4x4 and the extended cab had these little fold down seats in the back that folded out of the side of the wall and you had to sit sideways in the back. Only a midget could actually use them. I used it for hunting and fishing and drove it with little issue for 300k miles when the body started to rust out bad. I sold it to my cousin and he put another 100k on it and ended up using it for auto cross racing at the end. She went out with a bang, a great well used truck. RIP.
After that I owned a 2001 Saturn S-Series, a 1996 Chevy Corsica, a 2002 Chevy Malibu, 2005 Ford Explorer, 2014 Suburu Forester, 2012 Kia Forte, 2014 Kia Soul, and 2012 Honda Civic.
So I have owned 11 so far not counting a few I bought cheap, fixed and flipped. I usually roll with older used cars because they're actually more reliable than 2018ish or newer cars and I can usually buy 2-3 low milage used older cars for the price of a brand new car right now.