Don't know about 'craziest', but I've had a number of crazy fishing experiences.
In the 60's (the 1960's for the young folk here) I fished for sewin, the Welsh name for a migratory trout, on the River Teifi in West Wales. I was camped in a trailer at a nearby campground. I'd go out just before dusk, plant myself in the river among a row of other fishermen, and wait for the sun to go down.
Sure enough, just as it got dark, there was a "mad hour". I couldn't see a thing, and had to rely on the sound of the splash of the sewin, fresh from the ocean, trying to knock the lice off their backs.
I was fishing an Alexander, and would hit a fish virtually every cast. Occasionally, the fish would break the line or I'd flip the fly off during the back cast. That was fun, standing in the middle of the river in the pitch dark with the fly rod under one arm, a flashlight under the other arm, and attempting to tie on a new fly &/or leader.