My grandad spent the night in jail. He and several buddies were in the Air Force and traveling and didn't have enough for a motel so the local sheriff put them up in an unused cell. Got the prisoner b'fast in the morning, thanked the sheriff and drove on.
So, does this count?
Worked with a guy that had to go to some out of the way places to do an equipment survey for a government contract.
He picked a time when some reunion was taking place in one town, and all the rooms were gone.
The local cops were nice enough to offer him a cell for the night.