Before Jack Benny became the loveable skinflint he did in the 40's and 50's he was a much more sarcastic wiseacre in the 1930's. Though these episodes of the podcast are of less-than-ideal quality, they give you an idea of Jack's early character.
First his very first program going back 91 years to May 2, 1932. This is nowhere near what the program would become as Jack is less the star as he is the emcee of the Canada Dry program.
Then from March 8, 1936 for Jello, Jack takes the gang to the Central Park Zoo. This would have been much funnier with Dennis Day and Phil Harris.
Finally on April 5, 1936 in the middle of the Benny-Allen feud, Jack takes potshots at Fred Allen's radio program Town Hall Tonight with a parody entitled Clown Hall Tonight.
Apologies for the audio quality. These shows were not well preserved.