1989 Camaro RS with t-tops. A bad ### high school ride, my first car, gifted used from the folks (purchased for $6k or so), after I pulled a college scholarship (which was the deal struck some years earlier). Loved it, but folks had to sell it after pops lost his job (insurance was a small fortune...). Sad day seeing it go, even sadder that my dad felt like he let me down.
1986 Cougar - I think it was some time around this year. Dad purchased for a song from my grandmother to replace the Camaro, put a spoiler on it and some shiny sporty wheels and surprised me with it. Awesome, and after being back on the yellow school bus for a year, I'd have taken pretty much anything gladly
1988 Honda Prelude - Sporty little car, used off the Honda lot . Got it in black and put in one of those little red back-and-forth lights like in KITT. So stupid, but that's what teenagers do.
1998 C5 Corvette. Bought it new right out of college. Was my "I have arrived" car, but was kind of ridiculous for a 22yo to be driving it. Granted I was living in my parents basement still but had a decent job set up right after graduation and enjoyed it, pulled some hot chicks in it, one puked into the passenger side floorboards. Was a great vette design after years of clunkers from GM.
2000 Blazer - traded in the vette after deciding to go back to school, for something more practical.
Owned a motorcycle somewhere in here after getting rid of the blazer. Almost killed myself on it one night on the grand central. Decided after that no more motorcycles, ever. If I want to go fast, I'll do it in something that won't eject me and turn my melon into missile and leave me a vegetable in the end.
2002 BMW E46 M3 - purchased new in my last year of law school, after almost getting kilt on the bike. Awesome car. Got that ridiculous Laguna Seca Blue color, gorgeous, real head turner. Total waste of money as I would move back to manhattan and trade it in for something more practical soon enough
2004 Mini Cooper Sport. Traded in the M3. Drove this a couple years before going no car in Manhattan for a while (zipcar emerged somewhere in this period, good stuff).
2010 Audi A5 - purchased new off the showroom floor, awesome car. Beautiful and a blast to drive. Needed a car because I met this hot chick in another part of Brooklyn I wanted to spend some more time with. (6 years married and three kids later, I got my wish and then some....)
2012 Audi Q5 - With first kid en route, needed to go bigger. Also a great car
2014 BMW X5 - another kid on the way and wanted something slightly bigger. Leased this for three years and hated every minute of it. 400hp was awesome, but harsh, uncomfortable, jerky, overpriced. Decided no more BMWs. Traded that in to get a
2016 Yukon Denali. Bought certified pre owned with just 16k on the odo. Great family car. Really a truck, and drives like one. Massive, captains chairs, rear seat entertainment, and the engine from the Escalade so it moves. We'll keep this a decade, really the ultimate family mover.
2006 Land Rover. Bought used as a second car and loved it, except it had some engine glitch that would cause it to randomly stall. Totally unsafe. People talk about these cars having "ghosts" in the computers, and I saw why. FIL and I one night smoked several cigars in it with the windows closed when he was visiting in winter after our second arrived. That stench never left, and at trade in time my salesman called me out on it: Eventually got rid of it as a trade in for a
2015 Jeep Wrangler Sport Rocky Ridge Edition. Bought new. Bad ### weekend toy. Basically looked like a military humvee, Tank green color and jacked up on 35" tires, big bumpers, winch. Could drive this thing in then let rugged terrain, but mine saw at worst some pot holes in the mall parking lot. Really loved it for cruising around on a nice summer day but after the third kid arrived it was time for a more practical 2nd car. So only owned it a year, 2600 miles, then recently traded that in for a
2017 Audi Q7. Awesome car. Most incredible tech I've ever seen in a car. Love the design right down to the details. Blast to drive. Quicker than the 330hp suggests. Only complaint is I wish it had captains chairs, would make life easier getting eldest kid into the back row. But the reviews were stellar, so far we agree, and it just proved up for me that we like our Audis so much, such solid cars. It's not as spacious as the Yukon, but such a pleasure to drive.
With the Yukon and Q7 we are pretty set now, though Mrs. O wants me to get a weekend toy as a third car to replace my Jeep. I've got my eye on a ~1980 Jeep CJ7 Renegade for around $15-20k; I'd leave the doors off and top off year round and garage it, just bring it it on nice spring and summer days to toke on a cigar while running local errands; something like this:
https://classics.autotrader.com/classic-cars/1980/jeep/cj-7/100798787
I've taken a bath on nearly all the cars I've bought over the years, bought cars that were stupidly expensive and wasteful, financed them, and barely owned them long enough to break them in, be I've wised up a bit as an older Otis. We are finally at a spot where we own all our cars outright and it's a nice thing to not have to make a car payment. Hopefully won't for many years (ever?)