Ann Meara had her own comic genius. I would recommend younger Freepers search youtube for Stiller and Meara videos. Along with Nichols and May plus Bob and Ray, Monitor Radio was “must listen” on late 1950’s weekends
Another great radio show was "When Radio Was," but it was quite a bit earlier, with the original Jack Benny Show, Burns & Allen, Fibber & Molly and The Shadow. I used to stay up as late as I could on weekends, listening in bed, because I'd fall asleep while it was on (the local station aired it Friday and Saturday night, I think starting @ 11pm.)
Mark