The legendary Jack Benny was a gentle, generous man with no shortage of famous friends—and so beloved that even a headline-making scandal couldn’t put a dent in his popularity.
1. He Was A Reluctant Maestro
Jack Benny was born Benjamin Kubelsky in Chicago, Illinois, on February 14, 1894. His parents bought him a violin when he was six years old, hoping one day he would become a great musician. The good news was he loved the violin. The bad news was he loathed practicing. Still, he became an accomplished player—mostly to get out of doing things he considered way worse.
2. He Stunk At School
Benny hated school and homework. He was a daydreamer who played hooky frequently. When he did go to school, he pulled pranks, and they were disgusting. He enjoyed stuffing Limburger cheese into his homeroom radiators to stink up the entire class. He flunked out of high school and business college. His own father fired him from the family store.
It seemed the only thing Benny could focus on was that violin, so at 17 he joined the orchestra pit at a local vaudeville theater, ready to make some noise.
3. He Could’ve Toured With Groucho
Before the legendary Marx Brothers brought their comedy act to Hollywood, they toured the vaudeville circuit with their mother Minnie, stopping in Benny’s hometown of Waukegan, Illinois in 1911, Minnie noticed how quickly Benny picked up new music and offered him a job playing for her sons on tour. His parents wouldn’t hear of it.
They considered show business immoral and a waste of his talents—but they couldn’t keep him home for long.
4. He Heard Crickets Chirp
A year later, Benny was out of the pit and playing on stage with pianist Cora Salisbury. His parents only agreed to let them tour together because Cora was a respectable widow who promised to keep Benny safe from “loose” women. When Cora left the act, Benny toured for five years with musician Lyman Woods. They thought they’d hit the big time when they booked The Palace Theater on Broadway, but the act fell totally flat. With nowhere to go but down, Benny made a brave decision.
5. He Found His Voice
In 1917, Benny joined the Navy, often taking part in talent shows to entertain his fellow sailors. One night, the salty crowd booed his sappy song choice so loudly that Benny completely froze. But then he made a life-altering hail mary: Speaking to an audience usually gave him the shakes, but out of pure self-preservation, he managed to ad-lib a few jokes—mostly at the captain’s expense—and the men roared with laughter.
From then on, he began incorporating more comedy into his act. By the end of WWI, his violin was just a prop. He changed something else too.
6. He Gave Himself A Nickname
Back when Benny was performing with Cora under his real name, Benjamin Kubelsky, famous violinist Jan Kubelik had a hissy fit over the sound-alike name and threatened to sue. Benny started performing as Ben K. Benny, but in 1921, lawyers for comedian/fiddler Ben Bernie put pressure on him to change his name once again. This time he chose a nickname that sailors called each other: Jack.
Soon, the whole world would know him by that name.
7. He Was Best Friends With A Comedy Giant
Benny met fellow comedian George Burns during their earliest days in vaudeville, even before George married Gracie Allen and formed the iconic Burns and Allen duo. Neither of them would ever be the same again. Benny thought Burns was the funniest man alive, and sometimes would only have to look at him to start laughing.
They adored each other and were nearly inseparable for over 50 years—which meant George knew all of Benny’s guilty little secrets.
8. He Was A Ladies’ Man
Benny liked to say his shyness kept him from being great with the ladies. George Burns told a much more scandalous story: He claimed that Benny “slept with every girl from coast to coast”. He especially liked married women, and traded their names and phone numbers with other actors touring the circuit. Of course, this was when Benny was single. When he was in a committed relationship, he was all in—so much so that he almost married the worst person for him.
9. He Had A Crazy Ex-Girlfriend
Benny had an intense romance with a dancer named Mary Kelly. She was thirsty for drama and kept dumping Benny just so she could win him back again. She’d declare they had to get married, then say it was impossible because she was Catholic and he was Jewish. She’d tell him she never wanted to see him again, then demand to know why he hadn’t written.
“I guess she liked tormenting herself and me," Benny once said. By the time he finally ended things for good, his real wife-to-be was just around the corner.
10. He Slighted The Wrong Girl
The love of Benny’s life was his wife of 44 years, Mary Livingstone. She was only 17 when they met in 1921, and still known as Sadie Marks. Zeppo Marx had dragged Benny to a Passover Seder where the host thought Benny might like to hear his daughter Sadie play her violin. He thought wrong. Benny had no interest in listening to an amateur audition and told Zeppo it was time to go.
But Benny had made a terrible mistake: Sadie heard every word. She watched them leave—and began plotting her revenge.
11. He Wasn’t Good With Faces
The next day Sadie brought three of her friends to Benny’s matinee show and told them not to laugh at any of his jokes. He didn’t recognize her from the night before, but the stony-faced teens in the front row sure got under his skin. Two years later, Sadie tried to say hello to him backstage at a show in San Francisco. He didn’t have a clue who she was and politely brushed her off. The tables would soon turn in a hilarious way.
12. It Was Love At Third Sight
In 1926, a friend set Benny up on a date with the now 21-year-old Sadie. He fell hard and fast for the “smashing brunette with a vivacious smile," but she seemed unimpressed and declined a second date. Desperate to win her over, Benny showed up at the hosiery counter where she worked the next day. This time, he had a plan.
By the end of his visit, Sadie had broken her store’s sales record for stockings and Benny had a new girlfriend. Would you believe he almost lost her again?
13. He Forgot To Tell Her Something
Benny and Sadie dated for the next year, though he spent most of it on the road. He was mad about her, but just couldn’t—or wouldn’t— tell her he loved her. Sadie assumed this meant he wasn’t serious about their relationship, and when another suitor proposed, she accepted. Benny panicked and popped the question himself.
He and the girl he ignored at the seder married on January 14, 1927, unaware they’d soon be building their new life together in the Hollywood hills.
14. He Was Ready For His Close-Up
In 1929, Benny’s agent convinced movie mogul Irving Thalberg to go see one of Benny’s performances. This led to a five-year contract with MGM. His first picture, Hollywood Revue of 1929, was a huge success. His second, Chasing Rainbows, was a massive flop, and the next few weren’t much better. Benny got tired of waiting for the right vehicle for his talents and begged MGM to drop his contract. Thank goodness they did, because he was about to hit it big.
The Hollywood Revue (1929), MGM
15. He Was The Right Man For The Job
In 1932, soon-to-be TV icon Ed Sullivan invited Benny to perform on his popular radio program. His first words ever on radio were “This is Jack Benny speaking. There will be a slight pause while you say, Who cares?” Canada Dry was looking to sponsor its own radio show and decided to build one around Benny. He quickly became a household name and found fame with various sponsors on NBC and CBS. The Jack Benny Program was one of the highest-rated radio shows for over 20 years. So what was its secret?
16. He Flipped The Script
Benny took the standard radio format of telling a joke and introducing a song and crafted a style that became the blueprint for the classic sitcom. He understood most of the 30 million people listening from home were families, so he wanted to turn his cast into a family that audiences could relate to. He did this with running jokes, recurring characters, catchphrases, and also ditching sight gags that only an in-studio audience could see. Maybe most importantly, he decided everyone but the star should have the last laugh.
17. He Was A Laughingstock
Benny knew he’d get more laughs being the butt of his best jokes. He portrayed himself as a vain, put-upon, penny-pinching bachelor, surrounded by characters who always got the better of him. These included his sardonic valet, Rochester, the skirt-chasing bandleader, Phil Harris, multiple oddballs played by voice-master Mel Blanc, and several wise-cracking female foils played by his wife, now known as Mary Livingstone.
But there was just one problem: He was almost too convincing.
18. He Wasn’t Cheap
Benny was a generous man, but the public expected him to be as miserly as his TV persona. He didn’t want to spoil the illusion, so when it came to tipping at restaurants, he’d tell his servers to add any amount to the bill they wanted. It was always less than what he was willing to give, and he said, “If I sign the bill, no matter what I do, it’s not enough. If they sign the bill...they’re happy and I’m happy”. More than just a gimmick, Benny’s fake cheapness became a source of pride.
19. He Had A Favorite Joke
Benny’s “masterpiece of stingy jokes” went something like this: A thief holds Benny up, snarling the line, “You’re money or your life”. A long pause goes by—so long the impatient thief yells, “Come on, hurry up!” Annoyed, the notoriously cheap Benny finally says, “I’m thinking it over”. The in-studio audience laughed at this bit for over two minutes straight. It was an instant classic—just like his most famous fib.
20. He Was Forever 39
One of Benny’s most popular schticks was his straight-faced claim that he was only ever 39 years old. It was such a long-running gag that when he finally agreed to turn 40 for his 60th birthday in 1954, it made the papers. He devoted an entire show to the celebration only for his “sister” to call him at the end and tell him his birth certificate was off by a year, and that he was still 39.
But there was one big lie that everyone actually believed.
21. His Famous Feud Was Fake
Many fans thought Benny’s ongoing, on-air feud with radio star Fred Allen was the real deal, but the two were actually close friends. The comedians used to fling hilarious insults at each other over the airwaves thanks to their writers collaborating on such stunts as Benny hosting an “I Can’t Stand Jack Benny Because” write-in contest and Allen turning out to be the “surprise” celebrity judge.
But let’s face it. Everybody could stand Benny, especially his daughter.
22. And Baby Made Three
In 1934, Benny and Mary adopted their daughter Joan. They were waiting for another child, but that baby was late. Mary decided to take the frail-looking baby Joan home just for a few days to care for her, but she wound up falling in love and keeping her instead. Benny joked that he wasn’t impressed with the skinny, wrinkly little thing, and asked Mary “Is this the one you picked?”
It would lead to one of Joan’s favorite conversations with her father.
23. He Lost A Sweet Argument
Joanie was the apple of Benny’s eye, but he used to tease her by saying it took him two days to love her because she was such an ugly baby. Later, when he and his 7-year-old daughter were arguing over who loved the other more, Joan made the winning point, “I loved you all my life and you didn’t love me until the second day”.
Growing up with such a famous father meant sharing him with the world—or, at least, the neighborhood.
24. Everybody Knew Who He Was
In 1938, a magazine article named Benny the most recognizable voice in America, ahead of then-president FDR. Across the country, especially during the summer, a person could sit outside and not miss any of The Jack Benny Program because it was blaring through nearly every open window in the neighborhood. Somehow Benny remained humble—but he was only human.
25. He Loved Being Famous
Joan said her father loved being famous and never tired of meeting his fans and signing autographs. Once, she said, he took a trip to the Caribbean where nobody seemed to know him. After going a whole day without anyone asking for an autograph, he couldn't stand it anymore. He hopped on the next plane and went home to his fan mail. But it wasn't just praise he found in those letters.
26. He Responded To Fan Mail
Benny constantly received letters from grifters asking for money. One such person claimed to be a farmer who needed $50,000 to buy tractors to save his farm. He even sent photos of his sad, sickly-looking horses, waiting to be free of their plows. Benny mentioned the farmer to George Burns and—surprise!—he’d received the same letter and horse pics. So they came up with a hilarious scheme:
They both responded by sending the man two checks, well, two photos of checks for $50,000.
27. He Was Comfortable In A Dress
Benny started making films again and had a big hit with the 1941 comedy, Charley’s Aunt, in which he spends most of his screen time in drag, pretending to be the aunt of two Oxford classmates. Years later, Benny agreed to star in the Broadway revival of Hello Dolly as Dolly Levi opposite George Burns. Unfortunately, it never panned out, but you might be surprised where else he showed up.
28. Call Him An Easter Egg
It’s up for debate, but many believe Benny makes an unclear, uncredited cameo in the background of a nightclub scene in the 1942 classic, Casablanca. At the time, at least one theater offered free passes to anyone who could spot Benny in the picture. The film’s press book supposedly admitted Jack visited the set one day and decided to be an extra, but even famed film critic Roger Ebert wasn’t sure. Either way, there was no missing Benny in his next film.
Casablanca (1942), Warner Bros.
29. His Father Needed Convincing
Benny’s next movie was To Be Or Not To Be, a screwball comedy about a husband-and-wife acting duo set during Germany’s occupation of Poland. But someone in his family hated it...at first. His dad didn’t understand that the film’s opening scene, which featured Benny in a German uniform, was satire. He was so upset that he stormed out.
When Benny finally convinced him to watch it all the way through and he loved it. He later claimed to have watched it 46 more times. It’s just a shame that Benny’s favorite film was soon a source of heartbreak.
To Be or Not to Be (1942),United Artists
30. The Show Couldn’t Go On
Carole Lombard, who played Benny’s wife in To Be Or Not To Be, said shooting the picture was the happiest experience she’d ever had making a film. It was also her last. Tragically, she lost her life in a plane crash just before the movie premiered. She was only 33 years old. When Benny found out he was so distraught he couldn’t attend the preview screening. He also canceled his next radio show, something he rarely did.
To Be or Not to Be (1942),United Artists
31. He Blew It, All Right
Benny’s 1945 comedy The Horn Blows At Midnight, in which Benny plays an angel sent to end the world, was such a box-office dud that Benny used it as a punchline for years. In one of his better-known jokes, Benny waits at the Warner Brothers Studio gate for a security guard to let him in. “I was in The Horn Blows At Midnight," he says to prove his ID. The lowly guard responds, “I know. I directed it”.
Flop or not, Benny was still a major get for one Hollywood power player.
The Horn Blows at Midnight (1945), Warner Bros.
32. Benny Helped Win The Battle
For years, broadcast networks vied for top radio ratings, with NBC usually coming out on top. By the end of the 40s, television was on the horizon and CBS executive William Paley knew NBC would be unbeatable if he didn’t make a bold move. Sponsors, not networks, owned all the shows, so during what is now known as the Paley raids, Paley swooped in and signed Benny and other stars to CBS, ensuring the network’s dominance during the golden age of television. Benny was better than ever.
33. He Didn’t Miss A Beat
The TV version of The Jack Benny Program premiered Oct 28, 1950 and ran until 1965. It worked seamlessly in tandem with the ongoing radio show because it was practically the same. At last, folks at home got a good look at the characters they knew and loved, especially Benny with his signature fingers-to-the-face gesture and hilarious deadpan expression.
Mary Livingstone, however, rarely made an appearance, and for an unfortunate reason.
34. He Found A Solution
Mary had become increasingly nervous about appearing in front of any audience and was now at a point where the thought sent her into a panic. Benny’s answer to the problem was to have Joan read the radio lines live to the in-studio audience while Mary’s pre-recorded lines played at air time. Benny’s writers gradually wrote Mary off of the TV show, and changed the way they wrote for others as well.
35. He tried to Right His Wrongs
Eddie Anderson’s trademark rasp and comedic timing made his rockstar role as Benny’s wise-cracking valet, Rochester, a fan favorite. Early scripts leaned heavily into negative African-American stereotypes for laughs—even if Rochester always got the last one. Following WWII, Benny instructed writers to steer clear of jokes that perpetuated inequality. He also refused to play any theaters or stay in any hotels where Anderson wasn’t welcome. And he didn’t only have Anderson’s back.
36. He Spoke Up For Friends
Some of Benny's guests stirred up controversy: Shortly after Liberace appeared on Benny’s show, newspaper columnist John Crosby wrote a vicious article about his struggle to understand the popularity of the musician who looked like his “auntie”. When reporters asked Benny to comment, he gushed about Liberace being “the nicest person you’d ever want to meet” and said he was honored to have him on his show and would do it again soon. Is it any wonder that one huge star chose Benny’s show to make her TV debut?
The Jack Benny Program (TV Series 1950–1965), CBS
37. He Was Marilyn’s First Choice
Marilyn Monroe’s first TV appearance was on The Jack Benny Program in 1953. She was promoting her film Gentlemen Prefer Blondes and guest-starred as herself in a dream sequence. According to Benny, she didn’t want any money for the spot, but said she’d love to have “a really nice car," so he gifted her with a black Cadillac convertible. Marilyn may have played his dream girl, but someone else was his big celebrity crush.
38. He Put His Foot In It
Mary and Benny’s friends loved to tease him about his massive crush on actress Greer Garson, especially after one incredibly embarrassing encounter: He was out for a morning walk in Beverly Hills when Greer drove past, stopped her car, and called out to invite him and Mary to a get-together. Benny crossed the street to get her address and slipped on “the only mound of horse manure on Roxbury Avenue in 50 years”. He may have felt like a loser, but he was about to be a winner.
39. He Won!
As a gag, Benny made a surprise appearance on a 1957 episode of the quiz show The $64,000 Question. After answering his first question correctly he had to choose whether to play and risk his winnings, or quit while he was ahead. Benny decided to split. His category had been violins and he took home a whole dollar. And speaking of his trusty instrument...
40. He Saved Carnegie Hall
After years of convincing people he was a tone-deaf fiddler, Benny began playing charity concerts with his violin in earnest and realized his dream of playing Carnegie Hall. He returned to the venue in 1961 to help his friend, renowned virtuoso Isaac Stern, save it from demolition with a two-hour fundraising concert that aired on CBS called Carnegie Hall Salutes Jack Benny. By that time, he had upgraded his strings.
41. He Treated Himself
Another musical dream came true for Benny in 1957 when he got his hands on a coveted Stradivarius violin, which he bought for $16,000. Years later, he willed it to the Los Angeles Philharmonic Orchestra. It’s said that he once quipped, “If it isn’t a $30,000 Strad, I’m out $120”. Did you know, he was even a penny-pincher in animated form?
42. He Made A Great Mouse
In 1959, the Warner Brothers cartoon The Mouse That Jack Built spoofed Benny’s show. The cast voiced their animated counterparts—mice living in a hole in the wall of the real Benny’s home—but it’s a studio musician trying to mimic Benny’s “awful” violin playing in the score. “Man of a Thousand Voices” Mel Blanc provided the rest of the vocals in one of the few cartoons where he shared that credit.
The Mouse That Jack Built (1959), Warner Bros.
43. Someone Studied Him
Famed late-night talk show host Johnny Carson idolized Jack Benny and confessed to trying to emulate his iconic style. Johnny had once been an usher in the studio for Benny’s show and said he used to imitate the comedian’s gestures and sly pauses. Benny later became a frequent guest of Johnny’s, especially after The Jack Benny Program ended its long run.
44. He Bowed Out
The last episode of Benny’s show aired in 1965, but the star certainly didn’t retire. He performed stand-up and popped up on several popular TV shows. In January of 1974, Benny was all set to star in the film version of Neil Simon’s play The Sunshine Boys when he started feeling unwell and had to drop out. He pushed for George Burns to take his place, and it turned out to be a good decision; the following year Burns won the Oscar for the role.
45. He Made George Cry
In October 1974, Benny suffered a dizzy spell and numbness in his arms. Then, after experiencing stomach pains that December, he received a devastating diagnosis: He had pancreatic cancer. On December 22 he went into a coma, leaving the world just four days later. He was 80 years old. At his funeral, George Burns broke down giving his eulogy.
Bob Hope stepped in, saying, “This is the only time when Benny’s timing was wrong. He left us much too soon”. That he did, but not without arranging a last surprise for Mary.
46. He Sent Flowers To His Sweetheart
Whenever Benny was away from Mary on a trip, he would send her roses. The day after the funeral she received a single long-stemmed red rose from a florist. It happened the next day, and the day after that. Thinking it was a mistake, Mary went to the shop to inform them of Benny’s passing. They explained he’d arranged a rose delivery for every day of the rest of her life. She lived until June 30, 1983. It was maybe one of the few times Benny thought that far ahead.
47. He Never Had A Plan
Though he was once the most famous person in America, and helped shape the television industry in its earliest days, Benny’s tombstone describes him simply as “a gentle man”. Of his life and career, he said “Everything good that happened to me happened by accident...I never knew where I was going”. Humble words from someone who accomplished so much in just “39” years.
48. He Fell For It
Jack and George were both on friendly terms with Albert N. Chaperau, a charming Nicaraguan diplomat who, unbeknownst to Benny at least, had a secret side hustle of smuggling jewelry from Europe to New York for his wealthy friends. While on vacation in Cannes, Benny and Mary ran into Chaperau and accepted his gracious offer to bring their purchases home for them because he said his status meant he didn’t have to pay those pesky customs. Lies, Jack! His gullibility would soon come back to haunt him.
49. Someone Made An Enemy
Elma Lauer, the wife of Supreme Court Justice Edgar J. Lauer, was one of Chaperau’s best customers. She spent boatloads on expensive gowns and jewelry and zero on tariffs. When the Lauers fired their German maid over her political loyalties, she ratted them out to the US Customs Office. This resulted in a major scandal and an investigation into Chaperau’s other clients—which brings us back to Benny and Burns.
50. They Took The Stand
Charges that Jack and George had conspired to smuggle $2,131 and $4,885 worth of jewelry respectively soon arrived. George pleaded guilty and paid a $15,000 fine. Benny initially pleaded not guilty, but switched when his lawyer convinced him it was the only way to avoid jail time. The judge shamed him for being so gullible, ordered him to pay $10,000, and suspended a six-month prison sentence.
Thankfully, the public didn't hold it against him. In fact, Benny became more popular than ever.
Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19
