I guess I'd have to pick two. My first car, and my "first" car.
The first actual car was a 1989 Ford Escort, powder blue, with a terrible electrical drain somewhere in the system. So we unhooked the battery any time it was going to sit more than a day. I didn't drive it very much, I was 16 and rode the bus to school, but my dad drove it some. He patched holes in the floorboards with sheetmetal, pop rivets, and some kind of viscous black rustproofing sludge.
The one time I do remember driving it turned out to be the last time. I guess I was feeling rebellious or something (this was after my parents split up) and so I decided to go on an "adventure" and took it out for a drive with no particular plan. I ended up:
lost
at a Walmart in the town north of us (I bought an embarrassing CD there)
lost in the rain
drove too fast down a looping on-ramp and went straight into the grass, fortunately not making it all the way to the highway
lost in the rain and the dark
took a wrong turn at a fork in the road, left would've coincidentally taken me towards home, I went right
the car started to overheat and I pulled over
By this time, I was totally overwhelmed and exasperated and scared. I started walking back the way I came, hoping to find somewhere I could identify with an address and then call home to get help. I had a borrowed cell phone but I didn't want to call when I couldn't say where I was with any certainty. Well, mom called me first, and somehow was able to ascertain my general location, and came and got me. The car ended up getting towed later. It was apparently a bad water pump that did it in, and it went to the scrapyard, to be replaced by a bizarro version of itself, a 1988 Chevy Nova in powder blue that never ran and sat in our garage until it, too, was cut up for scrap. (My mom's boyfriend had some hand in bringing this abomination home and I denounce all knowledge of it.)
My "first" car was the first car I actually used on a regular basis, a 1998 Ford Taurus in dark green. (My plea to my grandma to buy me a 1992 Mercury Cougar XR7 from ebay was rejected and she got me this instead.) Now, this car was perfectly fine when we got it. Not special or cool, but a functional appliance of a car. No, the sketchiness accrued gradually over several years of ownership. To attempt to summarize:
A deer jumped in front of me and mashed up the hood and the plastic radiator support; this part actually got fixed nicely by insurance so it pales in comparison to the rest
I spun it on some slush and hit a farmer's barbed wire fence, scraping up the front bumper slightly
A Bronco backed into me in the Kmart parking lot and cracked the side of the rear bumper
I backed it into a picnic table at my friend's house by being a dumbass and broke the taillight (I later swapped the broken one and the good one for 1996-spec taillights from the junkyard, thus gaining sweet amber turn signals)
I misjudged the angle while parking at work one morning and smashed in the right rear door on the bumper of my boss's truck (he wasn't too mad since i only added some paint to his chrome bumper)
The rear brakes would lock up bad in the snow and I spun it more than once, this could have been also due to bald rear tires
I discovered that it burned a lot of oil when the oil light came on one day and I had to add 4 quarts to get it back to full (later I went on a road trip to Philadelphia and had to add oil during the trip; this has become a recurring theme in my life)
The turn signals quit working completely one winter and then started working again in the spring (the check engine light also did a similar thing)
In case the body wasn't mangled enough, I lost control in the snow (again, a recurring theme here) and overcorrected and slid sideways into someone's yard and took out their gas meter with the driver's door; the fire department and police were there, it was a fun time, the car got towed, it was mostly cosmetic damage but we had the underneath checked out and they might've replaced the oil pan or something I forget
Pretty sure it leaked coolant real bad too
eventually I sold it to a friend for 500 bucks and he drove it until the coolant thing got out of hand or something
So yeah, a lot of self-inflicted wounds there. And deferred maintenance. And Ford oil/coolant/turn-signal problems. Recurring themes in my life. *sigh*