Jack Benny presented himself on the air as an eternal 39 year old miser who didn't see the value in extravagance, even when it came to his on-again, off-again girlfriend (and real-life wife), Mary Livingston. Over the course of a grand total of 33 years between radio and television, Benny created his own little world that became the stuff of legend.
On the air, Benny had a housekeeper/valet/chauffeur, one Rochester Van Jones (Eddie Anderson), who was anything but your normal stereotypical African American of the period. Instead, Rochester proved to be as sly as a fox, often getting the better of Benny. Over the course of 23 years on radio (1932-55), Benny went through 3 bandleaders, most notably Phil Harris, who was spun off into his own series with wife Alice Faye, and Bob Crosby (Bing's brother). Most people might think that Dennis Day was the only "boy singer" Benny had, but that's not true, either. Day, who also landed his own show, was the 2nd one to occupy that gig, after Kenny Baker.
Day's role otherwise was that of a naive, well-meaning, but dim-witted 20-something who did his share of annoying and aggravating Benny. Then, there's announcer Don Wilson, often the target of jokes about his girth (as illustrated when the cast did a cartoon for WB, "The Mouse That Jack Built"; Wilson was represented by a plus-size mouse). Often heard from as well were Sheldon Leonard, Frank Nelson (neither of whom factor into our sample episode), and Mel Blanc.
Let's take a trip to 1948. Benny is able to smoosh together a satire of the Tyrone Power film, "Nightmare Alley" with a send-up of frenemy Fred Allen's Allen's Alley. Harris' character even uses Kenny Delmar's signature catchphrase, "That's a joke, son!".
If you ain't laughing, you ain't trying, pilgrims.