One of America's most beloved comedians, Jack Benny, captured audiences with his unique style that boiled down to the first line he uttered on radio: "This is Jack Benny talking. There will be a slight pause while you say, 'Who Cares.'" With impeccable timing and a penchant for becoming the butt of his own jokes, Benny's approach became keys to his enduring success. He was one of the first "natural" comedians, performing in a suit and tie and delivering jokes conversationally. On both radio and television, Benny excelled as a "reaction" comedian—earning laughs from his sidekicks who deflated his ego and poked fun at his notorious stinginess. Some of Benny's most memorable laughs came from his reactions. When faced with the demand "Your money or your life," his delayed response, "I'm thinking it over," epitomized his comedic brilliance. Born in Chicago but raised in Waukegan, Benny showed an early talent for the violin. As a teenager, he was an accompanist at a local vaudeville house and was offered a job with the Marx Brothers, which his parents made him decline. Eventually, he performed with Cora Salisbury before finding success as a solo act. Originally performing as Ben Benny, he changed his stage name to Jack Benny after a complaint from entertainer Ben Bernie. Adopting a sophisticated air, he was labeled "Jack Benny, Aristocrat of Humor" and even sang novelty tunes like "After This Country Goes Dry, Goodbye Wild Women, Goodbye." His Broadway appearances were met with mixed reviews, yet he honed his self-deprecating style and fall-guy persona that audiences came to adore. Benny's radio career began in 1932, hitting its stride by the late 1930s with a stellar cast including his wife Mary Livingstone, Don Wilson, Phil Harris, Eddie "Rochester" Anderson, Dennis Day, and Mel Blanc. Each sidekick had the opportunity to lampoon Benny's vanity and legendary thrift. Despite the jokes, Benny, known as one of the kindest men in show business, disliked the perception of him as a tightwad. At times, he curtailed "cheap jokes" to reshape his image. Unlike his contemporaries who relied on boisterous humor, Benny's shows featured thoughtfully scripted gags that evolved week to week. His mild catch-phrases like "Now cut that out!" didn't tire audiences, and his running gags, such as his perpetual age of 39, became beloved staples. Benny's radio tenure lasted until 1955, and he ventured into television from 1950 to 1965. He starred in "To Be Or Not To Be" alongside Carole Lombard, one of his cinematic highlights. Benny's influence extended beyond his shows; he was deeply moved when a school in Waukegan was named after him, the sports team humorously called "The 39'ers." Well into his 70s, Benny could still claim a youthful appearance and continued to attract audiences in live performances up until his passing. President Ford remarked upon Benny's death, "If laughter is the music of the soul, Jack and his violin and his good humor have made life better for all men." Benny's legacy as a comedic pioneer endures, leaving an indelible mark on American entertainment.