My two worst;

As driver - Got rear-ended by a semi on the way to work twice in succession. Not as serious as it sounds (light up ahead turned green, did not know my car was in front of him) but it gave me neck and back pain that was thankfully not permanent but I had to go to work on an important case before being able to go into the chiropractor. So I had to suffer at work for 5 hours before I could get away.

Overall - was front passenger in a car where we had stayed up all night, then left on a 5-hour trip at 2 AM. Sometime after sunrise, the driver fell asleep while driving on the interstate, drifted into the median, woke up and overcorrected, sending the car off the highway where we did a 3/4 rollover. Luckily, no one was hurt. Even more luckily, the car came to a stop about five yards from a ravine.