Sam Spade and Effie are the worst at it.
Same for comedians. Some can pull it off, some can't. Jack Benny's shows are still fresh and funny. Bob Hope's are cringeworthy.
I need to listen more to Hope. Red Skelton is unlistenable.
Jack Benny's stuff is the gold standard, but he did get funnier with age. The shows from the ‘30’s are hit and miss. Phil Harris is the funniest of OTR IMO. They're treasures which will stand up forever.