Mine was a 1965 Ford Mustang with no backseat and holes in the floorboard that I drove for about 6 weeks before I crumpled it. However, the rig I got after that I went through HS with... a Ford F100 with 3 on the column. I paid $600, which I financed at $50 per month. This was pretty much it, except mine was a different color. I had the biggest tires that would fit on the original rims, a kickin' 8-track player, and a cool scene shade on the back window.
A '62 Vomit Comet with a two speed Merc-O-Matic automatic transmission mated with it's pathetic 101 HP single carb straight six. Yes, it was as slow as it sounds, but beat the hell out of walking.
Got my license in 1989 and my first car was a total Guido jet black 1988 Iroc-Z. Auto with a shift kit. And...I totaled it after driving for only 6 months.
Ha, mine was a 67 Mustang with no power steering, no power brakes, no a/c or defrost, primer colored rust bucket with a straight six and a broken fuel gauge. I bought it for $500 and I swear I pushed that thing all over town because I always ran out of gas. It sounded like a lawnmower. My GF's dad at the time could always hear me coming around the block! You learn how to drive pretty quickly when you're driving something that hard to drive, that's for sure. After that experience you could drive a regular car through a tornado in your sleep and not get a scratch on it.
'90 Pontiac Grand Am. The front windows were not attached to the track, so I had to manually push the windows up and down. When I hit a bump sometimes the windows would come off the track and slide down inside the door with a big THUD leaving only 1/3 inch of window to pull them back up. Hurricane season I did some interesting things to keep the windows sealed securely. Plenty transmissions problems with it. Then the engine was jackhammer loud even with the best lube jobs.
1971 Toyota Celica I loved that car. Edit: I got it in '78 with a "if you can get it to run, or get it out of my driveway, you can have it" deal