Jack Benny became one of the most influential entertainers of the 20th century - by being the top radio comedian, when the comics ruled radio, and radio was the most powerful and pervasive mass medium in the US. In 23 years of weekly radio broadcasts, by aiming all the insults at himself, Benny created Jack, the self-deprecating “Fall Guy” character. He indelibly shaped American humor as a space to enjoy the equal opportunities of easy camaraderie with his cast mates, and equal ego deflation. Benny was the master of comic timing, knowing just when to use silence to create suspense or to have a character leap into the dialogue to puncture Jack’s pretentions. Jack Benny was also a canny entrepreneur, becoming one of the pioneering “showrunners” combining producer, writer and performer into one job. His modern style of radio humor eschewed stale jokes in favor informal repartee with comic hecklers like his valet Rochester (played by Eddie Anderson) and Mary Livingstone his offstage wife. These quirky characters bouncing off each other in humorous situations created the situation comedy. In this career study, we learn how Jack Benny found ingenious ways to sell his sponsors’ products in comic commercials beloved by listeners, and how he dealt with the challenges of race relations, rigid gender ideals and an insurgent new media industry (TV). Jack Benny created classic comedy for a rapidly changing American culture, providing laughter that buoyed radio listeners from 1932’s depths of the Great Depression, through World War II to the mid-1950s.