A very good friend of mine used to be absolutely notorious for losing his wallet.
For a while he lived in an apartment complex with a little man-made stream running through it. His dad went to visit him one time, and saw some money floating down the stream. By the time he got to my friend's apartment he had fished out a few credit cards, a couple hundred dollars, my friend's driver's license, and the wallet itself.
Another time this guy, one other friend and I were driving to Vegas from Orange County on a very windy Friday afternoon. Traffic was almost at a dead stop, and people were hanging out their windows, yelling at one another, and generally starting a fun and rowdy Las Vegas weekend while still on the road. I wanted to join the fun. But just to make sure I wouldn't fall out of the car when I climbed onto the passenger side window, I decided to open the door and slam it shut. What I didn't know is my friend had stashed his wallet (filled with about $500) between the door and the seat. So when I opened the door, the wallet flew out and money started swirling around like on that old Don Ho gameshow. Just at that moment traffic started to move. The guy who is not an idiot and was driving started to move, and I yelled "STOP THE CAR!!" So me and my buddy jumped out and started chasing loose bills all over the freeway. We managed to recover about $200.
And I haven't even mentioned his keys.