My tween son and I have been listening to Jack Benny radio programs for approximately two years. They're funny and clean, and mostly not problematic. And they're guaranteed to knock my son out at night.
The sad part is every single person associated with the show passed decades ago. We literally have no one to thank.
So, thank you Jack, Mary, Dennis, Rochester, Phil, and Don. You too Kenny, even though you kinda sucked.
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.
Anderson was a black comedian getting top billing and a high salary. His character often gets the better of Jack Benny, and is always treated respectfully (as respectfully as any of the characters, anyway.)
Compare that to "Amos and Andy" where two white actors play blackface and are often the butt of the joke.
I know someday he'll be ready for Lenny Bruce and Richard Pryor, but frankly, I'm just trying to get a boy to bed... ;-D
Recently, I enjoyed seeing Ernie Anderson in the original Brewster’s Millions. There’s something very satisfying about seeing his face instead of only hearing his iconic voice.