Not in high school, but when I was 18, my parents got me an old beat-to-hell Honda CRX from a friend who was moving away. They sold it to us for $20 because they needed to get rid of it and the transmission needed to be fixed anyway.
God, the memories of that stupid car and the countless breakdowns I had in it before I finally got a real job making good money and could afford a new car on my own.
The following stuff had to be fixed (not necessarily in this order) while I had the car:
Starter died.
Alternator died
Radiator died (this is when I got rid of it)
Fuel Filter clogged up, causing the car to jerk around when applying the gas (looked like it had never been changed. This on a 13 year old car with 120+ thousand miles.
Engine blew up inside and had to be replaced completely. Mechanic admitted he screwed up when he worked on the car last and ate the cost of the new engine so we only paid for labor.
Transmission had to be repaired.
Struts needed to be fixed but never did (front end shuddered a LOT at 55 mph and higher, which made it loads of fun to drive on the freeway)
Right front tire blew up. Somehow a stone worked into the sidewall and basically caused the tire to shred. Fortunately I was only going about 25 mph at the time.
Old alarm installed by previous owner had an exposed wire somewhere under the hood that kept brushing against the side of the engine compartment and triggering the alarm, somehow. Finally figured out how to disconnect the alarm. Real fun when this stupid thing starts wailing while you're on the freeway.
Battery died. Got a new one free under warranty.
Odometer died at about 130,000 miles. I put maybe 9,000 miles on the car before I got rid of that POS.
Replaced a broken headlight but screwed up the aiming on the new one.
Right front marker light screws fell out so half the time the turn signal would be hanging by a wire.
Right front turn signal got busted out.
Uggggghhhhh....
Also had some old guy back into me and crack the right front side body panel. Woo-hoo. Almost improved the looks of the car as it was.