I grew up listening to Jack Benny, and I was born in the 80s. KNX-1070 in Los Angeles used to play old time radio every single night, with Saturdays dedicated to comedy. It was great and really helped me to bond with my father.

I would caution you against trying to shield your son against “problematic” content, if by that you mean stuff that isn’t up to the precise current standard of political correctness. For one thing, such an effort is doomed to fail. For another, it may keep him from getting to experience some of the best comedy ever. For an obvious example, I’m grateful to have also grown up with the films of Mel Brooks, many of which are about as “problematic” as they come and yet still funny and even profound.