I have had some really strange local legend titles - often through commuting, where some of the longer segments are on roads that people wouldn't normally repeat. The oddest one was a segment near St Jean Pied de Port in the Pyrenees, which I used three times as it was a quiet way out of town and became the local legend on a segment 900 miles from home.
I briefly had a share of a KoM into Basingstoke. I was on a good day on the club run and there were two of us lining up for the sprint on the B3400, propelled by a solid tailwind. To my surprise I held his wheel up through Newfound and so was well placed for the sprint, probably the second time in 20 years of club runs, I've taken that one. I promptly sat up, and my friend continued past to the top of the rise, where the Strava segment turned out to end. He synchronised his ride, which was 4 seconds faster over the segment, about an hour later than me, at which point I was no longer equal top of the tree. I still had bragging rights for the sprint.