A couple of spooky stories come to mind...
-- When I was at WNAK in 1990-91 doing nights, I always heard strange noises coming from the third floor of the building (Bob Nielson had an apartment up there, but he supposedly didn't stay there often) and had weird things happen in the control room (e.g., piles of records falling, pots on the board turned up without explanation, strange humming in the mic and headphones). Just before I left, I was let in on the "secret" that the building was a former funeral home, and the studio was the former embalming room. I always wondered if that place was haunted.
-- Working at the old WILK building on Franklin Street doing overnights in 1989, I was told to stay out of the basement because homeless people would climb in there through a window and sleep there on cold nights. One night I heard some strange noises coming from the basement, so I called the engineer, who told me to go down and look around. As I got to the bottom of the steps, a cat (which had come in through the broken window) jumped out and ran past me. Somewhere on the wall is the imprint of my heart, which had leaped out of my chest.
A couple of quick funnies (though I cannot verify all of them actually happening)...
-- The story of Jim Ward taking a call live on his call-in "swap show" and having the caller yell the "F-word" repeatedly.
-- The automation at 104.9 in the late 1980s needed a babysitter to change the reels and spin if the system went down. If the system failed, a cart machine triggered and played "I think I'm in trouble" by Lindsey Buckingham. However, one day that song was mistakenly added to the rotation on one of the reels, causing major confusion when the babysitter went into the automation room to find the problem.
-- WNAK, when it first switched to a computer automation system a few years ago, played the exact same playlist week in and week out. Every song and commercial was the same each corresponding day for several months.
I'm sure I could go on and on...