Billboard vs Jimbo: The Jack Benny Show

I'm guessing you all have heard The Jack Benny Show so there's little need into going on and on about the show.

And I'm sure you have heard the show from many different eras, from the 1930's to the 1950's.  They are all different.

I think the show was probably at it's peak when Dennis Day, Phil Harris and Mel Blanc were on it; this would be the early 1940's before Dennis and Phil left for greener pastures.

Doing a bit of research, it seems that the funniest moment of the show was probably not the famed, "You're money or your life" question to Jack in a holdup scene but rather the evening when Don Wilson fluffed a line about famed news commentator Drew Pearson in which Wilson called him, "Drear Pooson."

From On the Air; An Encyclopedia of Old-Time Radio:

Immediately the writers summoned [Frank] Nelson to the booth and without Benny's knowledge or permission, changed his coming lines. Nelson was leery ("Nobody ad-libbed with Jack," he recalled years later) but agreed to do it if the writers would take responsibility. 

The scene arrived. "Oh mister! Mister!", Benny called. "Are you the doorman?"

At his absolute surliest, Nelson snarled, "Well who do you think I am, Dreeeeeear Pooooooson?"

Benny was instantly convulsed. "He began to laugh", Nelson recalled; "he slid down the mike to the floor, got up, staggered clear across the stage to the far wall, turned around into the curtains, pounded the floor some more. We're on live and laughter is going on through this whole thing." - Excerpt from On The Air; An Encyclopedia of Old Time Radio