You’re familiar with his work and his voice–he wrote the the basis for A Christmas Story and narrated it–and he had a long-running radio program back in the northeast where he would spend an hour minus commercials taking a topic and going off on a monologue with diversions about it.
In the middle 1960s, from whence these particular episodes come, contain the similar reflective humor from the curmudgeon genre. Kids these days, these modern things aren’t as good as they used to be, and so on. A little like Andy Rooney, but less cranky. A little like Dennis Miller, but less arch.
Sheppard covers different things, such as the difference in radio broadcasting technology, how Americans envy other countries their sense of stuffed shirt pomp, going to shows and the movies, regional accents, and so much more.
Each disc has a single episode on it, so the sample size is only eight shows, but it made for amusing but not laugh-out-loud funny on various car rides. My beautiful wife, however, did not like it, so perhaps the appeal is more towards the curmudgeonly amongst us.