My dad gave me his car when I turned 16 in 1992. It was a white 1971 Ford Galaxy 500. There was no way to hide in this thing, so I just had to embrace it. It was indestructible and the size of an aircraft carrier. This was during the big hooptie car craze, so it was actually very popular. I had about 100 black guys stop me and offer to buy it.
Looked like this one, but not nearly as nice.
After a few years, I purchased my 1st car. A 1986 Pontiac 6000 STE. Had a very fast 3.8L V6 in it. Got it up to 138mph. Pontiac tried to make it look all space age and digital inside. Lasted me all through college.
Upon graduating, I leased a 2000 Honda Civic Si. Also damn fast. Identical to this one. I think that lease was $159 a month.
In 2003, I turned in the lease and bought a Ford Exporer Sport Trac. Very functional.
Then in 2005, I bought my current F150 SuperCrew 4x4 when all the car companies panicked. Ford offered "employee" pricing and I picked it for $28,000. Currently has 160,000 mile on it. I have no plans to get rid of it any time soon. I havent had a car payment in 9 years.
Debating picking up a slightly used Accord or something (and keeping my truck). Using that as a daily driver for a few years, and then handing it to my daughter when she starts driving.
I love looking at all the nice cars, but never had the bug to spend any money on them.