My great great (maybe another great) uncle accidentally shot and killed himself while hunting. He was climbing over a fence and the gun went off. I think that was back in the 1930s.
My great great grandfather was killed in the 1950s or 1960s when he crashed his car into a combine harvester.
In the 1990s, my dad came out of his high school to leave. At the school, kids had to parallel park against the curb because the parking lot was reserved for staff. Anyway, my dad came out to his 1974 Ford LTD to find that some jerks who always bothered him had parked their small Mazda truck against his bumper so my dad couldn't leave. My dad went into the school and gathered a bunch of friends together and they literally carried the truck out of its parking space and dropped it in the front yard of the school.
Not long before I was born, my dad was driving a white C4 Corvette from the car dealer where he worked. He put a dealer license plate on it to make it legal and went to get gas. After getting gas, he drove to his best friend's house to show his friend the Corvette. My dad was in a hurry to get it back though. He sped off and while leaving his friend's street, he drifted around a corner and the license plate (which was held on by a magnet) flew off and landed in the road. My dad's friend saw it happen and had to sneak onto the dealer lot to give it back before my dad got in trouble.
Another time, my dad was driving a '93 Mazda RX-7 from the dealer and decided to "go the long way" back to work. He put the magnetic license plate in the window because the magnet wouldn't attach to the fiberglass/plastic body panels. He was speeding around, doing burnouts, and drifting through corners and a cop saw him. The license plate had fallen out of the window, so the cop was seeing a teenage kid driving an expensive sports car and being a dummy on the streets. The cop pulled him over and screamed at him and stuff rattling off an endless list of infractions, which would be bad for my dad at keeping his job. Luckily, my dad's boss, Bob, was known throughout the police departments as a friend. My dad was like, "Uh I work for Bob. You know, Bob?" The cop was like, "Oh yeah! I know Bob! Haha yeah he's awesome!" The discussion went on about Bob and the cop eventually said, "Yeah alright I'll let you go this time." My dad left scot free.