The Complicated Life Of Errol Flynn

Born in Tasmania in 1909, during the Golden Age of Hollywood, Errol Flynn became one of the most recognizable movie stars in the world. Best-known for his roles as a suave swashbuckler, his good looks and charisma made him one of Warner Brother’s most popular talents. Although Flynn may have been at the top of the Hollywood totem pole, not everything was as it seemed. There was a darker side to Flynn that involved countless women and a destructive hedonistic lifestyle. See the person Errol Flynn really was, and how his pedal-to-the-metal outlook on life led him to an early grave.

Trouble From An Early Age

Flynn school picture
Evening Standard/Getty Images
Evening Standard/Getty Images

Errol Flynn was born in Tasmania on June 20, 1909, and after spending some time in Papua New Guinea, he returned to Australia in 1926, to attend a fancy grammar school.

Nevertheless, that didn’t last all that long as he was expelled from the school. This was his first real encounter with public controversy, something he would become very familiar with in his professional life. While some stories claim that he was expelled for stealing, Flynn boasted that he was kicked out of the school for having intimate relations with a school laundress.

False Information

Flynn in a tuxedo
Sasha/Getty Images
Sasha/Getty Images

In 1980, one of Flynn’s biographers by the name of Charles Highman, falsely published in his book, Errol Flynn: The Untold Story, that Flynn had worked as a Nazi spy before and during World War II.

He claimed that Flynn had arranged for the movie Dive Bomber to be filmed on location at the San Diego Naval Base in order to provide the Japanese information about American warships and defense information. Highman also penned that Flynn was experimental and had numerous affairs with other men. It was only later that Highman admitted he had no evidence to back up his claims.

It Didn’t Take Him Much To Blow Up In Popularity

Flynn in Captain Blood
Warner Bros.
Warner Bros.

After having a few small parts in a limited number of films, Flynn found himself being considered for a big-time role in the big-budget 1935 swashbuckler film Captain Blood by Warner Bros. Although he was essentially unknown at the time, his initial screen test proved to be enough for the studio and the part was his.

The studio’s judgment turned out to be right and the movie was a smashing success, turning Flynn into a major star in the blink of an eye. By 1940, he was the fourteenth most popular actor in the US and the seventh in the UK.

He Was No Stranger To The Bottle

Flynn sitting down
John Kobal Foundation/Getty Images
John Kobal Foundation/Getty Images

Throughout his life, Flynn was known for his alcohol abuse. At one point, he even managed to get thrown out of a party hosted by William Randolph Hearst at Hearst’s Castle. On top of that, he once got into a physical altercation with director John Huston on the set of The Roots of Heaven for his behavior, resulting in him getting knocked out in one punch.

As a result of his drinking, he was banned on most sets from touching alcohol, so he was known to inject his oranges with vodka to get his fix. After his death of a heart attack, it was concluded that his liver was in such bad shape he would have died within a year anyway.

He Wasn’t Loved By All Women

Flynn and Davis
Bettmann/Getty Images
Bettmann/Getty Images

Although Flynn was a renowned ladies man for most of his life, there was one actress that saw right through him. She was Bette Davis, whom he worked on numerous films during the height of his career. Davis couldn’t stand Flynn, with him accusing her of slapping him overly hard in scenes just because she didn’t like him.

Davis attributed her hatred for him because she was forced to share a screen with someone she thought could only act in swashbuckler films. She once even told an interviewer, “He himself openly said, ‘I don’t know really anything about acting,’ and I admire his honesty because he’s absolutely right.”

He Was Denied From Serving In World War II

Errol Flynn in front of blue background
Silver Screen Collection/Getty Images
Silver Screen Collection/Getty Images

Even though he was a Hollywood star, that didn’t stop Flynn from answering the call of duty when the United States became involved in World War II. Although he tried to enlist in the military, he was rejected due to numerous health concerns.

Furthermore, Warner Bros. tried to cover up that he had been rejected, as it didn’t look good if their biggest action star was having health problems. This resulted in rumors spreading that Flynn had dodged the draft. Later in his life, he proclaimed that his only regret was not serving in the war.

His Son Was Lost And Never Found

Sean Flynn at a party
Earl Leaf/Michael Ochs Archives/Getty Images
Earl Leaf/Michael Ochs Archives/Getty Images

Flynn only had one son, Sean, who also became an actor. However, he eventually put acting on hold to follow his true passion for journalism. During the Vietnam War, Sean traveled to southeast Asia as a war correspondent for Time Magazine. Tragically, Sean disappeared while in Cambodia in 1970.

In 1984, he was eventually declared as dead although his body was never recovered and his cause of death was never confirmed. Luckily for Flynn, he wasn’t alive to suffer through this kind of loss.

Playing Robin Hood Defined His Career

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Warner Bros.
Warner Bros.

At the age of 28, Flynn starred in the 1938 film The Adventures of Robin Hood. The film turned out to be the 6th top-grossing movie of 1938 and was Warner Brothers’ first large budget color film using the three-strip Technicolor process, costing $2.47 million, it was the most expensive Warner Bros. film to date.

The film was hailed by critics and is still held in high regard today with Rotten Tomatoes writing in 2019 that “Errol Flynn thrills as the legendary title character and the film embodies the type of imaginative family adventure tailor-made for the silver screen.” It also won three Academy Awards.

A Relationship That Was Surprisingly Never Intimate

Flyn and Havilland in Captain Blood
Silver Screen Collection/Getty Images
Silver Screen Collection/Getty Images

Over the course of his career, Flynn made a total of nine films with Olivia de Havilland, more often than not as a romantic couple. Of course, rumors began circulating that the two were romantically involved off-screen.

Although this wouldn’t be a first for Flynn, de Havilland was firm in her response that there was no such relationship going on. She even later admitted that she felt a romantic attraction to Flynn but never acted on it out of respect for his marriage.

Flynn Found Himself In Deep Legal Trouble

Errol Flynn on trial
Bettmann/Getty Images
Bettmann/Getty Images

In 1942, Betty Hansen and Peggy Satterlee, two 17-year-old girls accused Flynn of inappropriate behavior at the Bel Air home of Frederick McEvoy and on Flynn’s yacht. The press had a field day with the scandal, although many members of the public sided with Flynn against the accusations.

The trial occurred in February 1943, with Flynn’s lawyer putting the girl’s character into question, citing that Hansen had an affair with a married man and Satterlee had an abortion, which was illegal at the time. He also accused the girls of working together in order to avoid prosecution themselves. Although Flynn was acquitted, the scandal permanently damaged his image.

He Had A Connection With Cuba

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Pinterest
Pinterest

In 1958, Flynn went to Cuba to self-produce Cuban Rebel Girls. There, he met Fidel Castro, as he was a supporter of the Cuban Revolution. Flynn went on to write a number of newspaper and magazine articles for the New York Journal American and other publications, documenting his time with Castro.

He was also the only journalist who was with Castro the night he learned about his victory in the revolution. Although many of his writings were lost in 2009, they were eventually rediscovered in a collection at the University of Texas at Austin’s Center for American History.

When Drinking Wasn’t Enough

Flynn on a boat
Hulton Archive/Getty Images
Hulton Archive/Getty Images

While it was well known that Flynn was a rampant alcoholic, that wasn’t the only substance that he was known to ingest. Over the years, Flynn began experimenting with a series of other substances.

According to his second wife, he was determined to experience as much as he could, which led him to try opium in the 1940s. Unfortunately, opium would become another addiction that he would struggle with for the rest of his life.

A Sick Joke

Errol in tuxedo
Silver Screen Collection/Getty Images
Silver Screen Collection/Getty Images

Flynn’s friend, director Raoul Walsh claims to have played a prank on Flynn the day after the death of John Barrymore. Supposedly, Walsh bribed the mortician to release the body to him. He then set the body up on a chair holding a drink inside of Flynn’s home.

In his autobiography, My Wicked, Wicked Ways, Flynn notes, “As I opened the door, I stared into the face of Barrymore. His eyes were closed. He looked puffed, white, bloodless. They hadn’t embalmed him yet. I let out a delirious scream. My heart pounded. I couldn’t sleep for the rest of the night.”

Always On The Prowl

Flynn and Nora
Bettmann/Getty Images
Bettmann/Getty Images

While on trial for the allegations of Betty Hansen and Peggy Satterlee in 1942, Flynn’s attention was on something else rather than possibly being found guilty.

That something else was Nora Eddington, a 19-year-old woman who was working at the cigarette cart at the courthouse during the trial process. It wasn’t long before the two struck up a romantic relationship, and the two were married in 1943. The couple had two daughters although they divorced in 1949.

He Was A Peeping Tom

Errol Flynn at home
John Kobal Foundation/Getty Images
John Kobal Foundation/Getty Images

In 1941, Flynn bought an 11-acre property on Mulholland Drive where he built a two-story colonial-style ranch house that he dubbed as “Mulholland Farm,” and more privately, the “playhouse.”

Inside of the house, Flynn had secret passageways that he had fitted with peepholes and two-way mirrors so he could spy on girls as they changed or were in the bathroom. On top of that, he also installed microphones so that he and his friends could listen to the women discussing the men.

He Was Quite The Womanizer

Flynn on fishing trip
Bettmann/Getty Images
Bettmann/Getty Images

Even before becoming one of the most famous actresses in the world, Flynn was known for his love of women, which only increased the more popular he became. According to his close friend David Niven, “Flynn’s attitude to women perhaps began with his strained relationship with his mother, Marielle. From age five, Flynn witnessed her affairs with other men, and she abused him regularly.”

Throughout his life, he was married three times and had countless affairs, with some of the notable women, including Joan Bennett, Ann Sheridan, Ida Lupino, and numerous others.

Issues With Director Michael Curtis

On the set of Robin Hood
Bettmann/Getty Images
Bettmann/Getty Images

Despite working together on several films over the years, Flynn and director Michael Curtiz were not friendly. It’s assumed that one of the primary sources of their animosity was that Flynn’s first wife, Lili Damita, had initially been married to Curtiz. On numerous occasions, the two became involved in physical altercations.

The first was when Flynn was struck by a sword without a protective tip that Curtiz had instructed to be removed, causing Flynn to grab him by the throat. The second happened after 25 of 125 horses died after Curtiz set up a line of tripwires while filming a pack of charging horses for a more dramatic scene.

Another Encounter With An Underage Girl

Aadland and Flynn
Bettmann/Getty Images
Bettmann/Getty Images

In the last two years of his life, Flynn was involved with yet another scandal when he traveled with a 15-year-old secretary named Beverly Aadland. The underage girl was also Flynn’s mistress at the time, and the relationship had been unbelievably arranged by Aadland’s mother, who would later proudly write a book about her daughter’s affair with Flynn.

In an interview in 1996, Aadland claimed that although Flynn initially forced himself on her, she grew to love him and wished they had more time together.

A Change In Titles

Flynn in a white t shirt
Hulton Archive/Getty Images
Hulton Archive/Getty Images

Errol Flynn was no stranger to embellishing stories or boasting about his accomplishments and exploits. So, it’s no surprise that when he wrote his autobiography, he wanted to title it In Like Me, a play on the saying “in like Flynn,” which refers to Flynn’s ability to seduce just about any woman that he set his eyes on.

However, Flynn’s publicist suggested that he go with something a little less aggressive and the autobiography was titled My Wicked, Wicked Ways.

He Almost Worked With Kubrick And Impressed Ernest Hemingway

Flynn in The Sun Also Rises
20th Century Fox
20th Century Fox

In the 1950s, Flynn met with director Stanley Kubrick to discuss the possibility of acting in his adaptation of Vladimir Nabokov’s controversial novel, Lolita, about a man obsessed with a 12-year-old girl. However, nothing ever happened, possibly because of Flynn’s muddy past regarding underage women.

In the last few years of his life, Flynn went from playing the leading man to alcoholic supporting roles. One of these most notorious roles was an adaptation of Ernest Hemingway’s The Sun Also Rises, with Flynn’s performance being the only aspect of the film Hemingway enjoyed.

Humphrey Bogart Was A Christmas Baby

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Hulton Archive/Getty Images
Hulton Archive/Getty Images

Humphrey Bogart has been hailed as one of the finest American actors to ever grace the silver screen, but success didn’t come easily to the New York City native. He didn’t hit the big time until well into middle age, with three failed marriages and a personal life that was in tatters. Golden Age Hollywood was reluctant to make a leading man of the sailor with a scarred mouth.

Humphrey DeForest Bogart was the eldest child of Belmont DeForest Bogart and his wife, Maud Humphrey. The precise date of the actor’s birth would be questioned for years. While Warner Bros listed his birthday as Christmas Day 1899, historian Clifford McCarty speculated that this was changed from January 23rd, 1900, “To foster the view that a man born on Christmas Day couldn’t really be as villainous as he appeared to be on screen.” His wife, Lauran Bacall, stated in her biography that Bogart celebrated his birthday on December 25, and the federal census records also confirm a Christmas 1899 birthday.

His Mother Was A Picture-Perfect Suffragette

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Buyenlarge/Getty Images
Buyenlarge/Getty Images

Humphrey came from good stock. His father was a successful cardiopulmonary surgeon, but it’s his mother who he had to thank for his creative genes.

Maud Bogart was a commercial illustrator, having received art training in both New York and France. She went on to become the art director of the fashion magazine The Delineator, as well as a militant suffragette, supporting the movement for equal rights. At her peak, Maud brought home $50,000, over $30,000 more than her husband. The star later described both of his parents as unsentimental, but straightforward. “A kiss in our family was an event,” he said.

Prestigious Schooling, Sullen Student

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Bettmann/Getty Images
Bettmann/Getty Images

Humphrey had the advantages that came with an Upper West Side childhood and well-to-do parents. He went to private school until fifth grade, moving on to attend the prestigious Trinity School in New York, before moving on to Phillips Academy, an elite boarding school.

While his parents hoped for their son to attend Yale, Humphrey wasn’t the least bit interested in academia. He was indifferent, moody, and was eventually expelled, supposedly for throwing either the headmaster or groundskeeper into a campus pond. Other sources state the expulsion was for raucous behavior, like smoking and drinking. With no clear future ahead, there was only one thing Humphrey could think of doing.

He Made A Better Seaman Than A Student

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Bettmann/Contributor
Bettmann/Contributor

His parents didn’t know what to do with him, and with no career prospects, Bogart decided to head for the seas, enlisting in the United States Navy when he was 18. To him, it wasn’t war. It was a holiday camp that paid.

“At eighteen, the war was great stuff,” said Bogart. According to records, Humphrey made a much better seaman than a student and is described as a “model” sailor. Some believe that his trademark voice and scar were a product of his service, having been hit by shrapnel during a shelling. Others, including Bogart’s long-time friend Nathanial Benchley, maintain that he was injured when taking a prisoner to jail. Either way, it would shape his career.

From Model Sailor to Struggling Stage Star

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George Rinhart/Corbis via Getty Images
George Rinhart/Corbis via Getty Images

When Bogart returned home from his duty, his father was sick and most of the family fortune was gone. He worked as a shipper and a bonds salesmen before landing a job at William A. Brady Sr.’s company, World Films.

Humphrey tried his hand at almost every aspect of filmmaking but found a talent for none. That was until he made his debut as a Japanese butler in the 1921 play, Drifting. Although he had been raised to think that acting was beneath his status, Bogart found that the late hours and attention suited him. “I was born to be indolent and this was the softest of rackets,” he later stated. Over the next few years, he would perform in several plays, where he would soon find his first real leading lady.

Short Marriage, Lasting Friendship

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Edward Steichen/Conde Nast via Getty Images
Edward Steichen/Conde Nast via Getty Images

While playing double roles in Drifting at the Playhouse Theatre in 1922, Bogart happened to meet the young actress Helen Menken. Menken and Bogart soon struck up a relationship and made it official in May 1926, tying the knot at the Gramercy Park Hotel in New York City.

The marriage lasted less than two years, with Menken telling court officials that her husband valued his career more than her, and she felt neglected. Although the two parted ways, they remained friends for many years. Six months after the divorce was finalized, Bogart married Mary Phillips, an actress much better known than he was at the time. This marriage would last ten years, but would also fall victim to Bogart’s ambition.

From New York to Hollywood and Spencer Tracy

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Donaldson Collection/Michael Ochs Archives/Getty Images
Donaldson Collection/Michael Ochs Archives/Getty Images

The stock market crash of 1929 meant that a lot of stage productions ground to a halt. Out of work actors were now beyond penniless and many camera-worthy faces headed to Hollywood to seek their fortune. Humphrey did just the same.

The young actor landed on his feet when Fox Film signed him for $750 a week. It was there that he met Spencer Tracy, another serious actor. Humphrey was enamored with him, inspired by his approach to acting. The two soon became fast friends, with Tracy coining the nickname “Bogie.” They would star together in one of the first movies to feature sound, Up the River. While the money was pleasing, Bogart was far from satisfied.

The Petrified Forest

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Donaldson Collection/Michael Ochs Archives/Getty Images
Donaldson Collection/Michael Ochs Archives/Getty Images

After work dried up in Hollywood, Bogart, now in his mid-thirties, landed a role as escaped murder Duke Mantee in Robert E. Sherwood’s play, The Petrified Forest. The play was a hit, completing 197 performances in New York in 1935.

Bogart’s performance marked his leap from the “smoothies” he used to play to serious, gritty parts. Critics praised his performance, as did his co-star Leslie Howard. When Warner Bros bought the screen rights, Howard was cast and insisted that Humphrey star with him. Warner Bros had other plans and tried to cast Edward G. Robinson, but when Howard said “No Bogart, no deal,” they relented. The movie was a box office smash and made Humphrey Bogart a household name.

A Favor Remembered

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Bettmann/Getty Images
Bettmann/Getty Images

Bogart knew that he owed his career to Leslie Howard. If Leslie hadn’t have insisted on him being cast alongside him in The Petrified Forest, then it’s unlikely that he would’ve had the chance of another big break.

In 1942 Howard was traveling from Portugal to Bristol, UK, when the aircraft he was in was shot down by the Germans. He was one among 17 fatalities. Some speculate that the Germans believed Prime Minister Winston Churchill was on the flight and that’s why they targeted it. In fact, Churchill traveled along a similar route the following day. Bogart paid homage to his friend by naming his only daughter Leslie Howard Bogart in 1952.

B Movies And Warner Bros Woes

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Bettmann/Getty Images

Although The Petrified Forest had catapulted Bogart from obscurity, he still struggled. Now tied into a contract with Warner that paid $550 per week, he was typecast as a gangster in a slew of B movie dramas.

This was during a time when studios held all the cards, and actors were told what parts they had. If they refused, they could be suspended without pay. Bogart was grateful for his success but didn’t like his new-found role of the gangster. “Nobody likes me on sight,” he once said. “I suppose that’s why I’m cast as the heavy.” Between 1936 and 1940 he was kept on a tight schedule, churning out a movie every two months.

Madness In His Methot

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Bettmann/Getty Images
Bettmann/Getty Images

While Bogart was making movies, it wasn’t as he had imagined it. With no freedom, poor pay, and at loggerheads with studio chief Jack Warner, he was drinking more than ever. He wanted his wife Mary to join him in Hollywood, but she refused, still performing in hit plays in NYC. The pair divorced in 1937, and Bogart married for the third time in 1938.

Mayo Methot was a friendly woman when sober, but a notorious drunk. She was paranoid, and as the pair continued to argue her drinking got worse and her behavior more erratic. Methot stabbed Bogart with a knife, set their house on fire and even slashed her wrists on multiple occasions. He was no angel either, often goading her. Julius Epstein described their marriage as “the sequel to the Civil War.”

Here’s Looking At You, Kid

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Sunset Boulevard/Corbis via Getty Images
Sunset Boulevard/Corbis via Getty Images

The 1940s marked a great change for Bogart. In 1941 he starred in High Sierra, a movie written by his friend John Huston. Although he still played a gangster, the character had more substance and it paved the way for Bogart to be considered a serious star.

In 1942, he landed his first romantic lead role in the classic movie Casablanca, alongside Ingrid Bergman. One of the most famous lines in the movie, “Here’s looking at you, kid,” wasn’t scripted. Bogart improvised it. The simple line became one a pop-culture staple and was ranked the fifth best line in American cinema by the American Film Institute.

Methot’s Nightmare, Lauren Bacall

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Silver Screen Collection/Getty Images
Silver Screen Collection/Getty Images

Over the course of their tumultuous marriage, Mayo Methot had always worried about her husband’s fidelity. It seemed impossible to her that a man in his position wouldn’t take advantage of the plethora of beautiful women around him. Her insecurity was at first unfounded. Then Humphrey met 19-year-old Lauren Bacall.

Bacall was blonde, tall, striking, and the two had instant chemistry. Despite the 25-year age gap, Bogart couldn’t resist her cheekbones and green eyes, while Bacall was infatuated with the handsome older actor. Still new to the industry, Bacall gratefully took the help offered to her by Bogart, who nicknamed her “Baby.” They began a discreet affair, sending each other love letters. The romance almost cost Lauren her career.

All’s Fair in Love and Movies

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Warner Bros./Getty Images
Warner Bros./Getty Images

Not everyone approved of the affair. Director Howard Hawks was very protective of Lauren. He considered her his project, a young actress that he would guide through Hollywood. Of course, he was hopelessly in love with her too.

He told Bacall that she meant nothing to Bogart, even threatening to send her to Monogram, the worst studio in Hollywood, if she didn’t end the affair. Lauren was devastated and Humphrey was enraged. Jack Warner eventually stepped in to settle the dispute, but Hawks would remain bitter about it. He would later say, “Bogie fell in love with the character she played, so she had to keep playing it the rest of her life.” Everything was against the couple, but they couldn’t let each other go. The studio saw an opportunity.

The One That Stuck

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Hulton Archive/Getty Images
Hulton Archive/Getty Images

Shortly after wrapping To Have And Have Not, the studio capitalized on the chemistry between Bacall and Bogart and billed them together for The Big Sleep. Filming was intense and the script was filled with sexual innuendo – by now the affair was tabloid fodder and Jack Warner wanted to milk it for all it was worth.

Bogart was in love with Bacall but torn between staying loyal to Methot. He had reservations about the age difference between them and was concerned that Lauren would leave him if he married her. “I’m afraid that you’ll become impatient and that I’ll lose you,” he wrote in a love letter to Bacall. “But even if that happened, I wouldn’t stop loving you.” In February 1945 he finally filed for divorce, and in May he married Bacall. “No one has ever written a romance better than we lived,” Bacall wrote in her memoir. Little did the pair know how short their time together would be.

The Demon Drink

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Popperfoto/Getty Images
Popperfoto/Getty Images

Bogie had always liked to drink. In his younger days, he preferred scotch but later switched to a martini. Many of his best friends, including Spencer Tracy, became his close confidants through late-night drinking sessions. Someone once said, “Bogart’s a helluva nice guy until around 11.30pm. Then he thinks he’s Bogart.”

His behavior, much like his ex-wife Methot’s, could become aggressive and abusive, and it began to affect his work. He once showed up in his pajamas and refused to work, instead riding a bicycle around the Warner Bros lot. During the filming of Sahara, he supposedly refused to leave his dressing room until he was given a thermos of martini. When asked if he had ever been on the wagon, Bogart replied, “Just once. It was the most miserable afternoon of my life.”

Bogart the Family Man

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Pictorial Parade/Archive Photos/Getty Images
Pictorial Parade/Archive Photos/Getty Images

Although Bogart was 48 years old by the time Bacall became pregnant at 25, he didn’t feel ready to be a father. The couple had been trying for children for three years, so when they finally conceived Humphrey was shocked. Bacall would later say that the day she told her husband she was pregnant was plagued by one of the worst shouting matches they had ever had.

In a letter he wrote to her the following day, he explained he was terrified of being an awful father. Their son, Steve, was born in 1949. They named him after Bogart’s character in To Have And Have Not, the movie that brought them together. The actor wasn’t exactly a natural father, but according to Steve, he tried. “Once I got to a point where I could talk and walk, he was becoming a family man. He didn’t want his children to take anything away from his relationship with his wife. He liked being married.”

Santana Productions and Freedom From Warner

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Silver Screen Collection/Getty Images
Silver Screen Collection/Getty Images

By the late 40s, Bogart was one of the biggest names in Hollywood. He now had a contract that gave him rights to refuse a script, albeit in a limited capacity. The success of Casablanca a few years prior had opened doors hitherto closed to him and he was subsequently offered a more diverse selection of roles.

In 1948, he went out on a limb and opened up his own production company Santana Productions, named after his yacht. Jack Warner was furious and worried that other big names would follow suit, diminishing power from his studio. Bogart did his last film for Warner in 1951. The early 50s saw him make a number of films through his own company, although most were flops. He sold his share in Santana to Columbia Pictures for $1 million in 1955.

The Rat Pack

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Earl Leaf/Michael Ochs Archives/Getty Images
Earl Leaf/Michael Ochs Archives/Getty Images

Few people realize that it was Lauren Bacall who coined the term “Rat Pack.” In the spring of 1955, her husband, by now showing the effects of years of alcohol abuse and smoking, was shooting the breeze with Frank Sinatra following a party in Las Vegas. Looking at the wreckage, she declared, “You look like a goddamn rat pack.” It stuck.

Bogart and Sinatra were firm friends, and it’s rumored that Lauren and Frank had a discreet affair. Bogart had his own mistress, having resumed a romance with his long-standing hairdresser. However, the couple remained happy and together, raising their two children. Bogart had great plans for new films, but his health was rapidly deteriorating. After persistent nagging from Bacall, he finally went to the doctor.

“Goodnight, Bogie.”

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Bettmann/Getty Images
Bettmann/Getty Images

Tests discovered that Bogart had cancer and required immediate surgery to remove a large part of his esophagus. His doctors were initially hopeful, telling the star that he would have to take time off to recuperate. Unfortunately, it soon became evident that Humphrey was not getting better.

Friends and family visited him over the course of the next year and left shocked at the frail man they saw. Years of abusing his body had caught up with him, and he died in January 1957, aged 57. He left behind his two young children and a devastated Bacall. In an interview, close friend Katherine Hepburn recalled visiting Bogart with her partner, Spencer Tracy the day before he died. “Spence patted him on the shoulder and said, ‘Goodnight, Bogie.’ Bogie turned his eyes to Spence very quietly and with a sweet smile covered Spence’s hand with his own and said, ‘Goodbye, Spence.’”