Jeremiah has never heard Jack Benny. Phil has him listen to three radio broadcasts from the 1940s. The two discuss Benny, his comedic style and influence. 

The episodes discussed are all available on archive.org:

March 28th, 1948: https://archive.org/details/JackBenny_HQ_601/JB_1948-03-28_Your_money_or_your_life_-_Ronald_Colemans_Oscar_is_stolen.mp3

April 4th, 1948: https://archive.org/details/JackBenny_HQ_601/JB_1948-04-04_Borrowing_Bing_Crosbys_Oscar.mp3

September 11th, 1949: https://archive.org/details/JackBenny_HQ_601/JB_1949-09-11_First_show_of_season_-_Stop_the_bus_-_Jack_is_only_heard_in_the_last_few_minutes_o.mp3