This topic has been immensely entertaining. I'll chime in (don't have any pics, though).
First major one was in my first car (a 97 Camry) when I was 16 or 17. I was driving home one night in heavy rain and thought I was the baddest driver around. Granted, I knew that little car pretty damn well and just how it handled, but I got a little too ballsy and decided to "drift" through some turns. First 2 went quite well. It's when I hit the third curve at 50MPH and pulled just hard enough on the E brake to lose control that things went south real quick. I over corrected (of course), "re-corrected," and finally turn 180* and slid off the 15 foot embankment somehow managing to dodge 4 huge trees on my jolting decent. That night put the much needed fear of God in me.
The second face palm moment is Taco related. I had just, a week prior, got my 06 4x4 DCSB sport 6 speed home from the dealership (this past May). The truck was in excellent shape aside from some tire wear, no body defects whatsoever. I decide to take her out on a maiden 4x4 voyage to the back of the farm. Everything goes well nearly the entire time of navigating logs, sink holes, creeks, ditches, rocks, hills, etc., was loving my new truck right up until I decide to head home and drive fairly quickly through a flat grass field where I knew there were no obstructions (so I thought). Turns out there had been a rather large tree downed since the last time I was there (more than the clearance offered by my stock truck on 265/70/17's). I never knew what happened until I had cleared it and went back to see what had fallen off the truck. Sure enough I found the downed tree trunk laying right next to my now dislodged spare tire...
Luckily, upon further inspection I discovered the only other damage was to the now warped skid plate I was very happy to have installed.