As a person who is interested in exploring the history of the entertainment industry I have seen a lot of film and television from long before I was born. A lot of things don’t hold up through a modern lens. Especially when it comes to comedy which can date easily. But when I look at the work of comedian Jack Benny, a man who has been entertaining people on the stage since the 1910s, I never fail to genuinely crack up the same way I do when I listen to modern comedians. I first discovered him in television reruns of The Jack Benny Program and his stuff holds up really well. He had a sharp sense of humor and he understood comedy better than anyone. Probably one of the reasons why he was one of the most popular performers for decades in the mid-20th century.

Benny was born Benjamin Kubelsky in Chicago in 1894 to parents who immigrated from Poland and Lithuania. Kubelsky studied the violin at age six with his parents hoping he would become a professional musician, although he hated the “practicing” part. Kubelsky did play in the high school orchestra but he was such a poor study, not just in music but in all his classes, that he was ultimately expelled. He didn’t do well in business school either but he discovered a way to make money using his violin in 1911 on local Vaudeville stages for $7.50 a week. It was even Vaudeville where he first became friends with the Marx Brothers. He was especially close with Zeppo Marx and at one point he entertained the idea of touring with the brothers (which his parents refused to let the teenager do).

Benjamin Kubelsky had actually changed his name twice. The first time was when the famous violinist Jan Kubelik feared that Kubelsky would damage his reputation due to their similar sounding names, which caused Benjamin Kubelsky to change his name to Ben K. Benny, and the second time was when Benny developed his one-man act “Ben K. Benny: Fiddle Funology” and received legal pressure from fiddle performer Ben Bernie, which caused Ben K. Benny to ultimately change his name to Jack Benny.

In Vaudeville, Benny performed violin music alongside pianist Lyman Woods for five years, slowly integrating comedy into their music act the more they performed. When the duo reached the Palace Theater (a mecca for Vaudeville talent) it was not a successful gig, nor were his gigs playing for the U.S. Navy during World War I. Although the sailors would boo him, Benny could often joke his way out of being heckled because he was a quick ad-libber, which once saved his performance from bombing. This actually helped establish Benny as more of a comedian than a musician, and in later years he would lean more into his comedy.

It looked like Benny might become a movie actor in 1929 when MGM signed a contract with him, his first role being The Hollywood Revue of 1929, but he did not have a lot of box office success. Benny starred in the 1935 MGM films Broadway Melody of 1936 and It’s in the Air, a lot of Paramount films from 1936 to 1940, and 20th Century Fox’s Charley’s Aunt (1941) which was one of Benny’s best films and one of his personal favorites, but Ernst Lubitsch’s 1942 black comedy To Be or Not to Be, set in Nazi-occupied Warsaw and starring Benny as a Shakespearean actor, is probably Benny’s most highly-regarded feature film and it is now considered a classic of American cinema despite many audiences in 1942 finding it in bad taste to make a comedy about Nazis during World War II. But Benny was well-cast and Lubitsch even pictured Benny in the role of Josef Tura while writing the screenplay.

Other films include George Washington Slept Here (1942, Warner Bros.), The Meanest Man in the World (1943, 20th Century Fox) and the film which featured Benny’s last starring role in a film The Horn Blows at Midnight (1945, Warner Bros.) which he often referenced when joking about being a box office failure later in his career.

During his lackluster career in the film industry, Benny turned to radio, which he was reluctant to try at first but soon started mastering, transitioning successfully from nightclub life to radio life, first being introduced to a wide audience by Ed Sullivan in 1932.

Benny’s weekly radio show The Jack Benny Program launched Benny’s popularity into the stratosphere in a radio run that lasted from 1932 to 1948 on NBC and from 1949 to 1955 on CBS with consistently high ratings. Jack Benny created a persona on his radio show that many listeners loved. That of a vain, penny-pinching and easily exasperated snob who could clear a room with his horrible violin-playing and assume it was because they didn’t appreciate his talent. Benny’s character was so hilarious and sharply defined that years into the show’s run audiences would eventually laugh at a joke before it was even told because they could predict how Benny would react to certain situations.

Other cast members included Mary Livingstone, Benny’s real-life wife and a naturally funny comedian in her own right who Benny first met through his friendship with Zeppo Marx and whose brother would go on to produce Benny’s radio and TV work; Eddie Anderson as Benny’s valet and chauffer Rochester; Don Wilson as the announcer and frequent sidekick; plus talented actors like Phil Harris, Mel Blanc and Frankie Nelson would often show up regularly and be equally hilarious.

The network television version of The Jack Benny Program, which is where I first discovered what a comedic genius Benny was, aired on CBS from 1950 to 1964 and on NBC in its final season from 1964 to 1965 and was just as funny as the radio show and arguably more so now that Benny’s deadpan facial expressions were added to the comedy stew. His move where he puts his hand on his face out of exasperation and stares out at the audience became a signature.

The television show featured many celebrity guest stars including John Wayne, Dick Van Dyke, President Harry Truman and even stars who rarely did television like Marilyn Monroe and Humphrey Bogart. Rod Serling once played himself in an episode that parodied The Twilight Zone and even Walt Disney appeared in an episode where Jack Benny tried to hit Walt up for free tickets to Disneyland and ended up escaping the wrath of Walt’s pet tiger by flying away on an umbrella à la Mary Poppins.

The Jack Benny Program was one of those shows that skewed towards older audiences in the age of baby boomers and it was a part of the wide variety of programs in the sixties purged by network executives to appeal more to younger audiences, but Benny grew weary of television’s demands by that point anyhow.

But I fully recommend checking out Jack Benny’s work. Especially The Jack Benny Program which is one of the rare comedies from the post-war era that feels timeless, despite the fact that it sometimes makes contemporary references that go over my head, but the Looney Tunes and Merrie Melodies series (which by the way featured an animated parody of Jack Benny’s show in the 1959 cartoon The Mouse that Jack Built written by Ted Pierce and directed by Robert McKimson) are similarly contemporary while remaining funny decades later. Somehow Benny just knew how to be both timelessly and universally funny. I can still watch it today and laugh.