And now after reading through this whole thread, I can weigh in as an official car guy (but not a gear-head).
Cars I've owned in order of preference:
1972 Chevy Impala. Lift kit in the rear, mag wheels, nitrous hook-up. At age 17. I lost my licence 3 time for speeding, paid over $1000 every 6 months for insurance when I was legally allowed to drive. I eventually sold it to someone who used it at Flat Rock speedway in Michigan. Stories made this car, not GM.
2015 Cadillac. Paddle-shifting vehicle with all the safety enhancements (like lane control, blind spots indicators, back-up cameras, self braking, etc). I put paddle shifters below tiptronic shifting, but well above manuals. I drive a twisty country road to work. Google puts it at 17 minutes drive time. I listened to AC/DC this morning and made it home in less then 6.
1996? Pontiac GTP Special Edition, limited availability wheels. This thing was so f*cking boss, I couldn't stop without gas station attendants asking what it was. It would top the list, but it's nickname was "bullseye". It was run over by trucks on 2 separate occasions (the 1st in the parking lot as I was dropping off my 1st car payment), had the left side trashed while parked on a street (probably also a truck), and then developed computer issues.
2009 Nissan Altima. A little more "family" then I like, bit an overall good ride
2011 Cadillac Yep, another one. This one was more entry model, but as my aged back was failing, comfort reigned supreme, and it delivered.
1969 Ford LTD "convertible". It was so f*cking big, it didn't fit in the garage. It could literally fit a BMW mini in the trunk. Convertable in quotes, because the top didn't go up. I still drove it in Detroit, all winter, as my only vehicle.
2002 Pontiac Vibe. A very sensible vehicle.
1975 Ford Grenada, the "Stealth Mobile". So named because I didn't get a single speeding ticket with this vehicle. It is assumed the rust absorbed radar. I was often profiled in this vehicle though. I am white, but I feel the poor black mans plight, because on some level I was similarly victimised by the police for driving this in nicer neighborhoods. It had a model airplane glued to the hood. When I drove, the propeller spun. I still think that's hilarious.
2015 GMC Sierra, 8' Bed. It holds everything.
2002 Dodge Neon. OK, this enters the shit list, but it was oddly fun having a vehicle I simply abused ontil I sold it for waaaaaaay more than any sensible person should have paid for a vehicle that had a broken speedometer, broken gear indicator, broken radio remote (yeah, it had a remote for a 3'x3' car) and broken air conditioner (in Tennessee). I parked it at the front of my house, it sold before I could walk 100' into the house. Thank you escalating gas prices.
2001 Dodge Dakota. Mini-trucks have both use and are easy to drive, but I'm not a fan of the manual transmission. Simply inefficient. The paint peeled off this thing like it was washed monthly with a brillo pad.
1998 Monte Carlo. This car looked cool, but it had so many issues, one day I dropped it off at the dealership and said Fuck you, fix this or I am done. I then walked to a Nissan dealership and decided to buy the first car I saw. As I came to my senses I told the dealer I needed to think about it. He dropped the price $2000. Deal done. Haven't owned a chevy since (sorry dad).
1982 Ford Escort. This thing sucked so much, it stalled one day, I got out and called a friend to tell him if he still needed a car, it was his - free. It was 2 years old.
I'm probably missing a few. cars are a little like women. Some are better than others, all are fun to ride, but as the years go on, you forget some of the in-betweeners).