Could one poor decision lead to a man’s downfall? That’s the story of George Jessel, whose career imploded because of one moment. Not only that, Jessel’s list of personal scandals became longer than his list of film credits. How did this happen? Let’s check the facts and see.

1. Fate Stepped In

George Jessel was born on April 3, 1898, in New York City—more specifically, Harlem. Both of his parents were Jewish and they were both involved in show business. Jessel’s father wrote plays and mom worked selling tickets at the local theater. Jessel’s father had not done well as a playwright and did not—under any circumstances—want his son to work in the theater.

Dad would have gotten his way, but fate cruelly stepped in.

2. He Had To Work

Yes, Dad didn’t want Jessel in the theater, but he couldn’t stop him. This was for a tragic reason:He didn’t live long enough. When Jessel was just 10 years old his father passed, and Jessel was required to bring home an income.

He started appearing in Vaudeville shows to bring money home for his family. Sadly, this wasn’t enough to put food on the table. Unattributed., Wikimedia Commons

3. His Mom Stepped In

Jessel’s next desperate attempt to become the breadwinner for his family was an inspiration. You see, mom worked at The Imperial Theater and she noticed that the patrons were often bored while waiting for the show to begin. With mom’s help, Jessel formed a threesome of ushers that entertained the patrons of the theater. They called themselves The Imperial Trio after the name of the theater.

This was certainly the start of something big.Architecture and building. v.56 1924., Wikimedia Commons

4. He Cried About It

Jessel learned a ton about show business while working the aisles at the Imperial, so he was soon ready to move on to bigger things. At the age of 20, he produced and starred in his own solo show, George Jessel’s Troubles. He then moved on to music: His first hit song was “Oh How I Laugh When I Think How I Cried About You”.

The plan was for Jessel to be laughing all the way to the bank.Photo by Mishkin, Wikimedia Commons

5. They Lost It

In 1919, Jessel was ready to make it big. He got a role in the silent movie The Other Man’s Wife. Set during WWI, the studio dedicated the film to the women who stayed at home while their men went to fight. I’d like to say what a great job Jessel did on his first film but I can’t—and it’s for a sad reason. The film has been lost forever.

Sure Jessel was making money as a film actor, but he never forgot the stage.Bert Sharkey (1886-1953), Wikimedia Commons

6. He Called Home

Jessel excelled in his vaudeville act and it soon became his bread and butter. There was one gag that he often repeated where he would pretend to call his mother and it always began the same way. “Hello, Operator! Fentingtrass 3522. Hello, Momma? Georgie!” Because of this engaging gag—with his unseen, but very Jewish mother—people often referred to him simply as Georgie.

Audiences loved to see Jessel call home, but would they love him doing anything else?Fox Films, Wikimedia Commons

7. He Was Number One

In these days, making movies was a step down from appearing on Broadway, and Jessel soon found his place there. He quickly became the number one leading man in Broadway productions.

One role that made him famous was in the drama The Jazz Singer. The play is about a Jewish actor who struggles against his father and his religion. He wants to be a famous jazz singer and his father won’t allow it. This was something Jessel could relate to—his own father was against him being in show business.

There was, however, something scandalous about this play.Warner Bros., Wikimedia Commons

8. It Is Forbidden

One thing that was pretty ordinary back then—but completely forbidden now—is performing in blackface. In his vaudeville act, it was common for Jessel to do this. In The Jazz Singer, which was actually based on the true story of Al Jolson, the character has to perform in it—it’s actually part of the story.

The play was a huge hit, but was it big enough for the big screen?Film studio, Wikimedia Commons

9. His Demands Were High

Warner Bros had already made Don Juan using a new system called Vitaphone to add sound to silent films. Now they were ready to use it again with The Jazz Singer.

Jessel was the one who had made the role famous on Broadway, so they turned to him for the film role. Remember, at this time Jessel was the number one guy on Broadway, so he wasn’t that eager to do the film. When he submitted his salary expectations to Warner Bros, they turned to their plan B.Los Angeles Times, CC BY 4.0 ,Wikimedia Commons

10. He Missed Out

Since the play was originally based on the real life story of Al Jolson, Warner Bros had what I would think was a very obvious idea: Get Jolson to play himself. So, when Warner Bros found out how much money Jessel wanted to be in the picture, they turned around and hired Jolson. But there was more to the story than that...http://pd56.org/the-jazz-singer/, Wikimedia Commons

11. He Wanted More

You see, Warner Bros did want Jessel to play the part of Jolson—they just couldn’t afford him. In fact they already owed him money from some of his past films. So, the obvious question I’b be asking is: If they couldn’t afford Jessel, why could they afford Jolson? There was one really good reason. Jolson had offered to help pay for the film.

While Jessel probably thought saying no to Hollywood and sticking to Broadway shows was the best option, this may have been the worst career move in history. unknown - press photo, Wikimedia Commons

12. It Was The End Of An Era

The Jazz Singer went on to become a classic. It was the first full length film to have lip-synchronous singing and synchronized music at the same time. The film also was the end of an era: Silent film wasn't long for this world.

Being attached to a project like that would immortalize any actor who starred in it. Jolson went on to a huge and successful career, while Jessel’s career was…well…meh. But was it really just The Jazz Singer that brought Jessel’s career down?Warner Bros., Public domain, via Wikimedia Commons

13. He Was Too Much

One of the other reasons that many people give for Jessel’s lackluster career in films is that he was too ethnic. A lot of Jessel’s on stage comedy revolved around being Jewish, including his famous call to his mother. Directors tended to see him as just one thing—and not capable of anything else.

Regardless, Jessel was convinced that The Jazz Singer had been his one chance at stardom and he spent a lifetime complaining about messing it up.

Sadly, there was more disappointment ahead.Acme Newspictures, Inc., Picryl

14. He Crashed

Jessel had clearly missed out on The Jazz Singer, and things were only going to get worse. In 1929 the stock market crashed and Jessel found himself in a financial mess.

He tried putting on stage plays, but people were in no mood for theater—they just wanted to put food on the table. Because of this dire financial situation in America, his stage plays flopped. But even though Jessel was in financial stress, he always had time for a joke.National Archives Photo, Wikimedia Commons

15. He Couldn’t Go Any Lower

One day, when Jessel was at his lowest point financially, he was sitting in a club with some show business friends. There was an announcement that Jessel had a telephone call. Jessel didn’t move an inch, and his friends wanted to know why. After all, it could be a job offer.

Jessel told his buddies that knowing his luck, not only would the call not be about a job, but he’d also rip his coat while walking to the phone. Jessel had hit rock bottom, but things would soon be looking up.George Karger, Getty Images

16. He Went Up

Jessel spent some time in Europe, and when he returned his career took a much needed upswing. In 1930, he appeared on Broadway in the musical Sweet and Low opposite Fanny Brice. Brice would go on to be the inspiration for the musical Funny Girl starring Barbra Streisand.

Instead of capitalizing on his reborn career, however, Jessel turned his attention to marriage.Bain News Service, Wikimedia Commons

17. He Did It Twice

In 1930, Jessel met and married Florence Courtney, who was an actor herself. The marriage was going fine until Courtney had a religious epiphany and…well…Jessel didn’t. This led to the two getting a divorce and then—to everyone’s surprise—getting married again.

The couple had stood the test of time—and divorce. Surely nothing could stop them now. And yet something did.Bettmann, Getty Images

18. She Had A Long Name

While Jessel was settling into his second marriage with Courtney, he met someone special, whom he called “the one great love that you never find a second time”. Luckily the woman also had a shorter name: Norma Talmadge.

Talmadge had been a huge box office draw in the era of silent films, but the advent of the talkies had not been kind to her. Jessel didn’t mind: He was in love. There were, however, a few obstacles in his way.Royal Atalier, N.Y., Wikimedia Commons

19. It Was A Love Triangle With Four Sides

Jessel was still married to Courtney when he met Talmadge. But it gets even messier. Talmadge was also married...to Jessel’s poker buddy. The truth was that Talmadge was separated from her ex-husband, Joseph M Schenck, who she was also in business with.

Because of their successful business relationship, Talmadge couldn’t convince Schenck to divorce her. The situation seemed hopeless—what could these love birds do?Bain News Service, Wikimedia Commons

20. It Was A Miracle

Jessel was so sure that Talmadge was the one, in 1932 he got a divorce from Courtney. This wasn’t well thought out because at the time, Talmadge was still married and unlikely to convince her husband to divorce her.

But in 1934 a miracle occurred. Talmadge finally got her husband to agree to divorce. Talmadge didn’t waste any time and immediately headed south for what they called a Mexican divorce. So, what the heck is a Mexican divorce?Keystone-France, Getty Images

21. She Wanted It Quick

In those days, it was not easy to get a divorce in America. You had to do annoying things like prove there was adultery or at least bad behavior. In Mexico—at this time anyway—all you really needed was a strong desire to get away from your spouse.

Talmadge got her Mexican divorce quickly and efficiently, just like Charlie Chapin had and how Marilyn Monroe would one day in the future.

Talmadge was now free from her husband and Jessel didn’t waste any time.Bettmann, Getty Images

22. They Tied The Knot

Just ten days after Talmadge had gotten her Mexican divorce, Jessel married her. This was on April 23, 1934. It had taken a lot of maneuvering to get here, but life was now going to be a bed of roses for the happy couple. Or so you’d think.

Don’t forget, this is Hollywood. Five years after all this hassle to get married Jessel and Talmadge called it quits. The marriage may have been over, but the drama was just getting started.Hulton Archive, Getty Images

23. She Was A Showgirl

Before long, Jessel got himself back in the headlines again. In 1940, he started dating Lois Andrews, a showgirl. While this doesn’t sound like a headline inducing story, you have to understand that Jessel was 42 at the time, and Andrews was still a teenager. The two dated and then shocked the country by deciding to get married.Boston Public Library, Picryl

24. He Gave Her Some Help

Around this same time, Jessel saw that his career as a performer was drying up. He made the decision to start producing musicals. Jessel wanted to help his new young wife get her career going, so he gave her minor roles in his films.

He also gave her something else: a daughter, whom they named Jerilyn Jessel. Yes, Jessel’s teenage bride was now a teenage mom.

Andrews, however, wouldn’t get a chance to get too comfortable: Her status was about to change yet again—this time not for the better.Boston Public Library, Picryl

25. She Got Demoted

By 1942, Jessel had married and had a child with 16-year-old Andrews. That same year he had another idea for her: How about a divorce? In two short years, Andrews had gone from teenager to wife to mother and now to single mom.

Nice guy that he was, Jessel continued to offer her minor roles in his musicals. He didn’t, however, offer her a role in this next film.Film Favorites, Getty Images

26. He Made A Gem

Jessel didn’t only produce musicals, he also made a foray into film noir. In 1947, Jessel produced Nightmare Alley for 20th Century Fox. This was a vehicle for Tyrone Power to change his reputation. He wanted to play a dark character and Jessel’s Nightmare Alley allowed him to do it.

Unfortunately, the film was a flop, and most critics thought it was too harsh. Modern day critics, however, have a different opinion of the film and now consider it to be a “gem of film noir”. Producing films wasn’t Jessel’s only pastime: He still had time to roast.Movie studio, Wikimedia Commons

27. He Roasted

Besides producing films, Jessel had another career: host. At this time there was something called the “banquet circuit” and Jessel made a living roasting his fellow celebrities at fancy dinners. Eventually this turned into a members only club called the Friars Club of Beverly Hills. Jessel, along with legendary comedians Milton Berle and Bing Crosby, were the founding members.

Jessel was becoming the most sought after host and TV executives took notice.Macfadden Publications page 2, Wikimedia Commons

28. It Was A Sure Thing

In the 1950s there was a TV series called Four Star Review that featured a rotation of hosts. Based on Jessel’s success here, ABC offered him his own show. The George Jessel Show had Jessel in his element.

It was a weekly roast of special guests all from show business. It seemed like it was a sure thing for success: It turned out to be anything but.ABC, The George Jessel Show (1953-54)

29. They Got Sued

The first problem with The George Jessel Show was a big one. One of the sponsors of the show—the BB Pen Company—sued ABC because some of the local stations that aired the show preempted it so that the pen ads weren’t always aired. The lawsuit that BB Pen Company brought to the courts was for $1.5 million.

The next problem was not about advertising, it was about quality.Boston Public Library, Picryl

30. He Got Canceled

The reviews for The George Jessel Show were worse than bad: They were abysmal. One critic placed the blame squarely on Jessel’s shoulders. He praised the guests, and even the production personnel, but for Jessel he saved his most unpleasant remark.

He called the show a “shabby excuse for entertainment”. They canceled the show after being on air for just six months. Was Jessel’s TV career over? Hardly.Boston Public Library, Picryl

31. He Tried It Again And Again

Of course, getting canceled hardly kept Jessel off the airwaves. In 1958, Jessel had another show, this time more of an interview and variety show. It aired from September 1958 to June 1959: less than a year. At least it lasted longer than the last show!

There was even another try in 1968: George Jessel’s Here Come the Stars. This one also didn't last a year. It seemed that Jessel couldn’t make it work on the small screen.

Where Jessel did flourish was in the headlines—but not the good kind.George Jessel Productions, George Jessel's Here Come the Stars (1968–1969)

32. He Was Back In The Headlines

In 1961, when Jessel was 63 years old, scandal reappeared in his life. Actress Joan Taylor came forward with a stunning announcement: Jessel was the father of her daughter Christine. Jessel was quick to deny the accusation—but then he said something that landed him in even hotter water.General Photographic Agency, Getty Images

33. He Took It Seriously

When Taylor announced that Jessel was the father of her child, Jessel didn’t take the news very seriously. Instead of making an official statement, he just said that being the father of an illegitimate child of Taylor’s was a compliment.

Someone must have given him some strong advice because soon Jessel was telling a different story. He indeed was the father, and he agreed to pay child support to Taylor.Michael Ochs Archives, Getty Images

34. He Donated

Jessel was very philanthropic and, over the years, donated his talent to the USO. He went overseas to entertain servicemen in WWI and II, Korea, and Vietnam. He became so well known for his hosting abilities that he received this title: “The Toastmaster General''.

Jessel says that at this time he was traveling a whopping 13,000 km (8,500 miles) every week.Ben Martin, Getty Images

35. He Got Recognized

Because of his devotion to the USO, Hollywood wanted to honor Jessel. They couldn’t exactly give him an award for his acting as he hadn’t really wowed audiences that much with that.

In the end, the folks at the Academy Awards cooked up a special offer for him: In 1969 he received the Jean Hersholt Humanitarian Award. I can say with some certainty that Joan Taylor didn't applaud too hard when that was announced.

Jessel surely had two opposing sides, and that was also true politically.Ron Galella, Getty Images

36. He Wanted Them To Go

Jessel had a particular comedy style that had been very popular—but it was now fading. There was something else that people thought was outdated: His response to the situation in Vietnam.

Jessel very openly supported sending Americans to fight in Vietnam. While he wasn’t alone in this opinion, it would probably have alienated a good chunk of his fans.

Jessel had been coming across as very conservative politically, and then he did a complete about face.United States Army Heritage and Education Center, Wikimedia Commons

37. He Played For Both Teams

When it came to equal rights, Jessel moved from the right to the left team. He spoke out against race-related prejudice and anti-Semitism. He even found himself kicked off a televised interview once.

Jessel was talking about The New York Times and decided to compare it to Pravda, which was the propaganda machine of the USSR. The interviewer on theToday Show didn’t feel comfortable with Jessel’s comparison and shut the interview down.

University of Southern California, Getty Images

38. He Bared All

In 1975—when he was 77 years old—Jessel wrote a tell-all autobiography called The World I Lived In. Well, the world he lived in contained a few romantic entanglements with some big stars of the time.

According to Jessel, he had affairs with femme fatale actress Pola Negri, torch singer Helen Morgan and wild girl Lupe Velez, AKA the Mexican Spitfire. Whether this is the truth or an old man fantasizing about what could have happened, we’ll likely never know.

Yes, Jessel was fond of spinning yarns—and it was hard to tell what was true and what was just said for a laugh.Andrew L. Stone Productions/United Artists, Wikimedia Commons

39. He Wanted A Favor

As he got older—and as his cohort began to pass—Jessel became famous for his eulogies at funerals, especially for famous people.

Once when Jessel was sitting around with his pals the Marx Brothers and Jack Benny, an older man walked up to Jessel to ask a favor. The man wanted Jessel to write and perform a eulogy for…get this…his dog. Jessel was outraged and told the man that he did not do eulogies for animals.

What the old man said next made Jessel change his mind.Denver Post, Getty Images

40. He Did An About Face

The old man continued to try and get Jessel to perform a eulogy for his dog. As a last resort he offered Jessel $2,500. Then he went one step further. He said he would donate $25,000 to the United Jewish Appeal. Jessel’s reply to this has gone down in history. He accepted that man’s offer and added: “You didn’t tell me the dog was Jewish”.

Hulton Archive, Getty Images

41. It Was A Morning Drink

The Hillcrest Country Club had a special table put aside for comedians and Jessel often sat there to hang out with fellow funny men like George Burns. One day Burns was shocked to see Jessel wolf down three shots before it was even nine o’clock in the morning.

When Burns asked Jessel what was up, he got a reply that made him laugh.Joan Adlen Photograph, Getty Images

42. He Had His Reasons

George Burns wanted to know why Jessel was slugging back the drinks in the morning, and Jessel was ready with an answer. He asked Burns if he had heard that his ex wife Norma Talmadge had passed.

Burns was shocked because Jessel’s ex had been gone for 35 years. So, why was he drinking now? He told Burns: “I still miss her”. It seemed that nothing could stop Jessel’s humor, not even his own demise.Bain News Service, publisher, Picryl

43. He Wouldn’t Quit

Once he hit a certain age, giving eulogies for departed friends and fellow performers took up most of Jessel’s time. As the time for his own eulogy approached, Jessel just kept right on working.

By this time the poor man had advanced arthritis and was blind. Sure he was a bit of a relic from a bygone era, but there were enough people out there who remembered him and wanted an easy laugh. Sadly, Jessel’s days were numbered.Gotfryd, Bernard, photographer, Wikimedia Commons

44. He Lives On

In early March 1981, Jessel—now 83 years old—was still performing. On the 23rd of that same month, Jessel had a heart attack and it was all over. Sadly, it seemed that we would never hear the sound of his distinctive voice ever again. Well, it wouldn’t be forever.

You can still hear it every time you watch the animated series Futurama. Voice actor Billy West used Jessel’s voice as an inspiration when he was creating his popular character Dr Zoidberg.John Preito, Getty Images

45. He Brought An Unwanted Date

Jessel was against prejudice of any kind and it wasn’t just about the words he used, it was also in his actions. Back in the day, there were some restaurants and clubs that didn’t permit Black people to enter.

One day, Jessel showed up at the door of the Stork Club and asked for his table. This wasn’t unusual in itself as Jessel was a regular at the club. The problem was who his date was: performer and civil rights activist Lena Horne. Studio publicity still, Wikimedia Commons

46. There Was No Reservation

Even though Jessel had made a reservation for himself and his Black date, the head waiter at The Stork Club was trying to find some reason not to seat them.

He pretended that he couldn't find the booking and then asked Jessel who had made the reservation.But Jessel had a quick and witty response: “Abraham Lincoln”. The waiter was flustered and found a table for Jessel and Horne.

Jessel’s life was full of anecdotes like these—probably enough to fill a book.Time Inc.; photograph by Alfred Eisenstaedt, Wikimedia Commons

47. He Invited Her In

Shirley Temple was a rare thing: a child star who continued to have a career as an adult. In 1964, Jessel told a 35-year-old Temple that he wanted to discuss a role with her for one of his films.

When Temple got to Jessel’s office, it became clear that Jessel was after something other than her acting ability. It started with Jessel putting his arm around Temple. Then it just got worse.Unknown author, Wikimedia Commons

48. She Got Out

According to Temple, while Jessel had his arm around her, he also managed to get his pants off. His arm then went from her shoulder to her chest. Temple had faced this kind of casting couch behavior back when she was just 12 years old, so she knew enough to go into attack mode.

She kicked Jessel in his groin and she fled. With behavior like this, Jessel becomes a very unlikeable man. He did, however, have a whole different side to him.Internet Archive, Picryl

49. He Found Them

Shortly after he’d divorced Norma Talmadge, Jessel found out that his ex-wife already had a new lover who happened to be a doctor. This infuriated Jessel and he wanted to let her know how much. Jessel then found out that Talmadge and her doctor lover were in Florida together.

He flew all the way there and found Talmadge’s hotel room.He entered the room with a plan: a dangerous one.Keystone, Getty Images

50. He Wasn’t Alone

Both Talmadge and her lover were in the hotel room and it soon became apparent that Jessel wasn’t alone either: He’d brought a pistol with him. Jessel fired some shots at the lover and somehow managed to completely miss him.

According to comedian George Burns, the shots missed the doctor, but hit a gardener who was two blocks away. The gardener lived, and the story went down in Jessel history.

Joan Adlen Photograph, Getty Images