Well then... spill. Tell us what tidbits you heard please :)

There was actually a musician who incorporated phone scanners into his work (under the appropriate stage name "Scanner"): https://en.wikipedia.org/wiki/Robin_Rimbaud https://www.discogs.com/Scanner-Scanner/master/1767734

In the '90's I worked with a bunch of ham operators in a building next to Route 95. Perhaps the most interesting call that we heard was a guy who kept switching between his wife and his girlfriend. IIRC (it was many years ago) neither one was happy with him.

Late 90's, I heard all sorts of stuff. The one that really stands out was a girls basketball coach who was in town for a tournament on the phone with a prostitute, talking to her about the need for discretion.

Cordless phones were pretty common during that era, and they were just as trivial to listen into. Teenage me had a hard time looking the neighbors in the eyes afterwards though...

Oh yeah, I remember when they started advertising with 'encrypted' cordless phones.

You just needed an old analog TV. The UHF tuner would pick up AMPS.