I don't know years but this is the rough order:
First car, 17 years old:
90'something Pontiac Grand Am SportProbably the foxiest car I've owned. I bought it off my sister who thought she could buy a new car, move into an apartment and not work all in the same month. It was a sport tuned 2 door with all red dash lights, a 'stealth' CD player, full sunroof and drove like a go-cart (in a good way).
I was never a car person but I just happened on a really decent car for high school and early college. Axle broke at a stop light first year of college (very lame death). Back seat was tiny (still managed to bang in it), was low as hell (bumps were painful), and I got a 72 in a 25 school zone ticket that was transferred into "Failure to obey traffic control signs" so I didn't lose my license (it was my 2nd day).
1992 Chevy CorsicaThis car went through hell. It was white (initially) with red interior and I drove it until it fell to pieces. I got $75 extra because I could actually drive it to the junk yard for cash-by-weight trade-in. It never left me stranded or failed. Just all the little things broke (window controls, dash stuff, arm rest, door handles, radio etc). I think taps was playing as it was driven off through the great mounds of metal.
1998 Buick CenturyHunter green and fuckin' awesome. I love Buicks. You don't go left or right in a Buick, its port and starboard. I could fit 6 people in this car and 5 dead hookers in the trunk. The thing ran forever and was so damned comfortable. The back AND front seats were bench seats (hence 6 people). This car had quite the personality at my work place and school, everyone loved the Buick.
Once my boss said I should think about getting a more respectable car since I was moving up in my career and I laughed at him, "That's what you would do".
The end goal for this car (and my girlfriend's matching red buick regal) was to have a demolition derby in a local quarry with shotgun passengers firing paintball guns out the window at targets painted on the cars. Sadly the Regal got totaled while parked and the Century's brakes broke a few years later (170+).
2000-somethin' Chevy ImpalaDidn't last long as it was just a transition vehicle. Notable event is some plastic chain got caught on the exhaust (catalytic converter) melted, and got my girlfriend and I pretty fucked up driving upstate once. We had to pull over at a rest stop and just passed out on the grass for 45m.
2002 Buick LeSabre (Current)Return of the Buick! This car is ballin'. Pressure sensitive windshield wipers, headlight sensitive mirrors, heated seats, heated mirrors, driver profiles, auto-everything. It even has an automatic feature to drive 55 in the left lane with your left turn signal on. The ultimate old man's car.
I really do love it. Again, seats 6, windows are splinted up in the back since they are off their tracks (I have better things to spend $500 on). This car has a nose ring since the hood-pop cable broke and wasn't long enough on the inside so I routed it out the front with a ring on the cable. Honestly, its the best place to have a hood pop cable.
1992 Harley-Davidson XLH 1200 Sportster (Current)My vehicle of choice. I've put 6,000+ miles on it this summer alone. I love this bike. It is completely mechanical (not fuel injected or computerized in anyway) so I can work on every part of it without crazy specialized tools or expensive chips. I've ridden it down to Virginia and up to the finger-lakes of NY. It is loud, fast, powerful and just falls into corners; it's nimble as hell. For the longest time I didn't "get" motorcycles. Now I do, and I love them.
The bike has a lot of custom parts (it is hard to spot the model for most folks) including:
Forward foot controls (regular sportys have 'under the hips' controls)
Custom gas tank
Bullet signals (old style ones were huge bug-eyes)
Performance air filter (matches tank)
Corbin seat (with obnoxious flames, soon to be fixed)
Lowered rear suspension
This winter I am going to take off the fenders and tank and get them painted, not sure on the color yet. Also getting a new rear fender as this one is pretty worn out and I don't like the style of it. It'll be an opportunity to re-wire the whole thing as well.
The fun bit about Buicks and Harley's is if you ever met me, they're the last thing you'd think I'd drive/ride. I probably look like a guy who should be driving an Audi but fuck'em, cars are a necessary evil and bikes should be heard a few blocks before you see'em.
Last weekend's ride through west jersey farm country, I had the bags on (not typical) because I was bringing someone some wine.

