These are flyers from a radio program called The Radioman that ran decades ago. They are all black & white and all somewhat stark. They all share a similar layout, and while I am certain they all belong to the same program, I cannot guess if the 11:00 AM program is a re-run of the 9:00 AM program. It may just be the same program in a different time slot.
It's not always visible in my scans, but the the image always has Xerox burns but the framing logo and time slot are crisp. On the originals I can see white paper tape, a product used in flyer design in the 1980s. WECS only came on air in 1979, so that collaborates the bottom end of our time frame. Wikipedia notes an early 90s era which jives with what little else we know.