Not the dumbest, but perhaps one of the more memorable.

I once tried to take this good looking blonde fishing in the dark at the back pond.  Got my truck stuck, then proceeded to get dad's truck stuck while shucking his front ring and pinion trying to get my truck out.  Just couldn't quit and nearly buried a tractor getting them both out.  Fish could have lived in the ruts I dug in the hayfield and about the time I got everything pulled out I could make out his shadow standing on the back porch watching the show from ~300 yards away.  By the time I got everything back to the house a small crowd had gathered and was waiting for the outburst. Hilarity struck when he broke out the "she sure is perty" line after assessing the damage.  

I have no doubt, the decision to square bale instead of round bale for the next two weeks was made in his sleep that morning.