In "On the Air: The Encyclopedia of Old-Time Radio" by John Dunning, one of Jack Benny's most well-known comedic moments is highlighted. During a skit where a robber threatens him with “Your money or your life!”, Benny's reaction unfolds with increasing hilarity as he pauses to contemplate the choice between losing his money or his life. This moment showcases Benny’s unique ability to blend suspense with comedy, keeping audiences engaged with his timing and the absurdity of the situation.

This gag is emblematic of Benny's style, characterized by his signature blend of wit and charm. By taking a moment to think it over, he builds tension while simultaneously creating a comedic scenario that leads to laughter. Benny masterfully navigates through the absurdity of the threat, demonstrating how he uses character and humor to turn a serious moment into a memorable comedic experience that resonates with listeners even today.