Besides rods and reels I've seen some weird stuff tossed overboard. I was on board a boat once when a sex blow up doll was discovered while looking for a blanket. The inflatable full size doll was blown up and tossed overboard. On the way back in, we caught a nice dodo under it.

This wasn't the same one that GS and I saw tied up to the weather buoy a few years later.
The most expensive thing I ever saw go overboard was a nice engraved O/U shotgun. The guy was shooting clay birds off the transom and lost his footing. I've also seen a couple outriggers cut in half by poor shooting. I've seen people get bored and take out a 44mag pistol and start shooting at the trolling lures.
I've seen camera's, hats, bikini's, cigarettes, gaffs, ghetto blasters, shoes, lures, rubbers (Trojans), tampons, portable fighting chairs, hammock's, frying pans, poker chips, backgammon boards, dice, beer, whiskey, and even money tossed into the deep blue.
I've also seen and done the flying human trick. With the boat running at full throttle, you do a running jump off the transom into the rooster tail of the wake. Creative flyer's will do flips. This normally happens when people have had to much to drink. Last time I was airborne into the rooster was about two years ago. I won't do that any more even if money is on the table as a dare. I was sore for weeks. When I was in my twenties, I'd stand on the outboard engine while at full throttle and chug a beer to impress the girls.
