Mine are mechanical mishaps induced by teenage driving of my first Datsun, a 710 Hardtop.
While driving around 45 mph and nearing a corner, my friend screams "PUNCH IT!" and so I did, got sideways, over-corrected, and smacked the curb, shredding rim and tire. My friend laughed non-stop for the next 24 hours.
While driving around late night, the same friend dares me to run over a 4' clump of Pampas Grass. I thought "Well, that's an easy one!" and proceeded to accerate toward, up, and stuck on top of that clump of grass. My friend laughed non-stop for the next 24 hours.
I also experienced the loose wheel lug nuts problem, but I didn't realize it until I heard a "BANG!" while driving down my street, then a griding noise, and finally, noticing one of my wheels pass me up and smacking into the neighbor's hedge.
Last, I was playing it "cool" by not setting the handbrake while parked in the garage, even though our driveway was sloped. I was inside attending to important business when I heard a "CRUNCH!" and ran out to see my car had done a slow, backward roll into a palm tree.
Funny, those memories still haunt me to this day, and I haven't seen that friend in years either!