In the “Golden Age” of Hollywood, life wasn’t exactly a breeze for even the biggest stars. Money-hungry studio executives controlled actors’ roles, schedules, and daily lives, feeding bright, young talent to the La-La-Land machine. Actress Olivia de Havilland hated the system. So, she pulled a legendary stunt that’s still talked about in Hollywood. And though she passed in 2020 at the age of 104, her move will be felt in the movie business for decades to come.

Discovered by Hollywood agents in a university production of Midsummer Night’s Dream, Olivia de Havilland signed with Warner Bros. Studios in 1936. Excited to make it in the business, she said “yes” to every role she was offered.

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Her first successful roles were those opposite dashing actor Errol Flynn in The Charge of the Light Brigade (1936) and The Adventures of Robin Hood (1938). The two became an onscreen duo: de Havilland as the beautiful damsel in distress and Flynn as the charming swashbuckler.

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Her chemistry with Flynn onscreen was undeniable, and many people wondered if there was something going on between the two of them off screen as well. But in the end, de Havilland claims nothing went on between them. She had bigger plans for herself.

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After her initial fame, de Havilland was eager to grow as an actress. She wanted to play more complex characters, but she kept getting just more of the same. She was typecast as the ingenue role: innocent, naive, and beautiful, but not much else.

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For example, in 1938 she starred in the romantic comedy Four’s a Crowd as a ditzy rich girl caught up in a financial scandal. Later that same year, she did Hard to Get as… yet another ditzy rich girl. By this point, she was having some serious doubts about her career’s direction.

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So she approached Jack Warner, head of the studio. “I was really restless to portray more developed human beings,” she said. “Jack never understood this … he would give me roles that really had no character or quality in them.”

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Frustrated with Warner Bros., she set out to convince the studio that she deserved better roles. She began by networking. Her idea was, if she could be on good terms with influential people involved in casting, she’d get better parts.

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In the process, she got to know Ann Warner, the wife of Jack Warner. This relationship would be key to her plan: de Havilland had her sights set on a particular role outside of the Warner Bros. studios and with MGM on a little film called Gone With the Wind.

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De Havilland wanted the role of Melanie Hamilton Wilkes, an intelligent and morally dignified character that had agency and complexity. She knew this was the role she needed to take her career to the next level and break out of her typecasted mold.

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After cultivating a friendship with Ann Warner, the two went to Jack. As he put it, “Olivia, who had a brain like a computer concealed behind those fawn-like eyes, simply went to my wife and they joined forces to change my mind.”

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Finally, Jack was persuaded: She was permitted to work on the film, which became one of the most iconic pieces of cinema in American history. She was nominated for an Academy Award for her performance, and she thought that when she went back to Warner Bros., she would continue getting high-quality roles.

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Except, that’s not what happened. In what seemed like some serious pettiness, she was cast in 1939’s The Private Lives of Elizabeth and Essex alongside her former on-screen flame, Errol Flynn. The lead went to Bette Davis, and de Havilland was relegated to playing a lady-in-waiting!

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The quality of her roles didn’t get any better. By this point, de Havilland had had enough. She refused roles she was assigned and stopped working, leading to a series of formal suspensions from the Studio.

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This continued for years, with de Havilland fighting for roles she wanted and outright refusing to play ones she knew were beneath her acting talent. She fought long, drawn-out battles with the studio, always standing her ground.

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After seven years, de Havilland’s contract with Warner Bros. expired, so she said “goodbye,” eager to move on. However, the studio claimed that her contract had not been fulfilled, since all the time she spent not working didn’t count. She was still technically under contract!

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Obviously not one to turn down a proper fight, de Havilland sued the studio. The case went all the way to the California Supreme Court, and, after lengthy court hearings, the judge finally declared in de Havilland’s favor. No studio, he said, could retain contract rights over an actor for more than seven years.

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The decision was one of the most groundbreaking in the industry, and the “seven year rule” is still commonly cited in Hollywood as the “De Havilland Law.” Of course, Warner Bros. was not happy about this loss, and fought to have de Havilland blacklisted from major studios in the industry.

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However, after enough time had passed, she continued to work in Hollywood in a variety of roles for nearly 50 years, all the way up into the ‘80s! Afterwards, she retired in Paris, and continued to serve as a sort of grande dame of Hollywood.

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Olivia de Havilland was the last of the stars of Hollywood’s Golden Era. When she passed in 2020 at 104, she left behind a legacy that paved the way for actors and actresses to have full control over their careers. Of course, her iconic co-star had his own struggles with the industry.

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Once he hit Hollywood, Errol Flynn turned into one of the world’s leading men — the prototypical hero. His road to the top, however, started on the other side of the planet.

Flynn actually hailed from the island of Tasmania. Even as a young boy in the quiet Battery Park neighborhood, he had a brush with celebrity; Errol simply had a knack for the spotlight.

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In World War-era Australia and New Zealand, events known as “queen carnivals” were held to raise money for returning soldiers. It was at one of those festivals that Flynn got his first taste of celebrity.

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There, nine-year old Flynn served as a page boy to Enid Lyons, who would go on to become a major figure in the Australian political landscape. Even at a young age, he was apparently still a charmer.

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Lyons never forgot Errol. She later remembered him as “a dashing figure — a handsome boy of nine with a fearless, somewhat haughty expression, already showing that sang-froid for which he was later to become famous throughout the civilized world.”

As he grew older, Flynn would leave Tasmania. He spent two years at school in England before landing in the metropolis of Sydney, Australia. Even though he was closer to home, things weren’t easy.

In 1926, Flynn enrolled in the prestigious Sydney Church of England Grammar School; he didn’t last long on campus, though. While the official word was that Flynn was expelled for stealing, the actor told another story…

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In his autobiography, Flynn claimed that he was caught in a compromising position with the school’s laundry woman. While no one is quite sure what actually happened, would you doubt Errol’s powers of seduction?

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With his schooling done, Flynn struck out on his own. He tried to find a fortune in tobacco and mining but, before long, he got his first chance as an actor.

In 1933, an Australian filmmaker was looking to make a movie about the mutiny on the HMS Bounty. While Flynn wasn’t actually related to any of those famous sailors, as rumors suggested, he still landed a role.

After that, Flynn set his sights on becoming an actor; he then headed to England, hoping to make his name as a marquee star. While he found work, he also found himself in more trouble…

When working with the Northampton Repertory Company, Flynn threw a female stage manager down the stairs. That attack didn’t end his career, however, as the actor eventually moved on to Hollywood. His star was (slowly) on the rise.

Errol landed a few bit parts before filming a screen test for Captain Blood. He wasn’t a big name actor, but studio executives like what they saw; the movie was a smash hit and Flynn became a star.

In 1938, Flynn landed his iconic role as the star of The Adventures of Robin Hood. It solidified his reputation as Hollywood’s leading man, capable of sword fighting and saving Maid Marian with equal ease.

In his personal life, however, things weren’t as perfect. When World War II rolled around, Flynn wanted to enlist in the armed forces. Various medical issues, however, disqualified him from service.

Neither Flynn nor the studio wanted to admit that the star was unfit for war; consequently, critics derided him as a draft dodger. In the star’s personal life, though, things would still get even uglier.

In 1942, two 17-year olds accused Flynn of statutory rape. The trial was ugly all around. The girls’ character was publicly questioned, and while Errol was eventually acquitted, the world no longer saw him in the same light.

Although the star continued appearing in movies, his career was never the same. Flynn drank heavily and abused drugs; he also became too old to be a swashbuckling leading man anymore.

Eventually, the actor fell into financial difficulties. During a 1959 trip to Canada to try to lease his yacht, Flynn had a fatal heart attack. An autopsy also revealed a life of hard living took a toll on his liver.

Back then, movie audiences were shocked to learn that actors could be so remarkably different than their characters. Flynn’s contemporary James Cagney, right, ran into that same issue with his tough guy persona.

Instantly recognizable for his staccato voice and shock of red hair, James Cagney reached the level of fame where everybody could do an impression of him. That’s how much the actor stood out. His family, however, never expected him to see adulthood.

Born to an impoverished family in 1899, James was perpetually ill as an infant. Two of his siblings died soon after birth, but he somehow pulled through. Once his health was no longer in question, Cagney had the privilege of growing up in the most colorful environment imaginable.

His earliest memories took place in Manhattan’s Lower East Side, an immigrant neighborhood packed with every food, fashion, and language known to man. Although Cagney was a mix of Irish and Norwegian, he learned to speak perfect Yiddish from his neighbors.

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Despite his short stature, Cagney developed into quite the athlete. When he wasn’t boxing or playing baseball, Cagney was dancing. He picked up tap dancing and displayed a freakish ability to master complex steps after seeing them performed just a single time.

Cagney’s adaptability brought him a number of small-time acting roles across New York, though he still held a day job. Toiling away as a bellhop at the Friar’s Club, Cagney came in contact with a bunch of professional actors and figured he was just as talented as them.

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Soon, the virtuoso landed his first professional gig, though not in your typical show. He (pictured third from left) joined the cast of Every Sailor, a comedic all-male drag revue. That brought him more opportunities in vaudeville productions and a couple bit parts in movies.

However, stardom was just around the corner for Cagney. He found his breakout role in 1931’s The Public Enemy, where he cemented his bad boy status by smacking a grapefruit into Mae Clarke’s face. As iconic as that scene became, it wasn’t even in the original script!

The filmmakers were inspired by a real-life anecdote about a gangster flipping an omelet into his girlfriend’s face. Because there was already a grapefruit lying around set, they decided to pay homage to this infamous outburst. It paid off.

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The magnetic Cagney established himself as the premiere mobster actor of the 1930s, highlighted by the classic Angels with Dirty Faces. Meanwhile, he also showed audiences that he could do more than glower at the camera. The tap dancer went back to his vaudeville roots.

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Released just after America’s entry into World War II, Yankee Doodle Dandy provided Cagney with one of his favorite roles. His musical chops earned him an Academy Award for Best Actor. At that point, Cagney could do anything he wanted.

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He continued to shine on the silver screen, with his leading part in White Heat becoming one of the most terrifyingly memorable performances ever. But by that point, Cagney was interested in more than just acting. He wanted to permanently change the way films were made.

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Behind the scenes, Cagney became president of the Screen Actors Guild. While he often played gangsters in movies, he had no patience for the actual mafia, who had a history of interfering with show business. Cagney gave them the boot.

The mobsters, however, didn’t take this decision lying down. Allegedly, they engineered a plan to murder Cagney by dropping a heavy stage light on him. The SAG president’s many connections, fortunately, managed to get the Mob to call off the hit.

Cagney’s idealism also cost him sometimes. Because he supported the anti-Catholic leftists during the Spanish Civil War, producers of Knute Rockne, All American refused to cast him. The silver lining there was that the iconic part went to Pat O’Brien, Cagney’s pal who helped save him from the mafia.

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His unflagging personal convictions also made the leading man a true romantic. The moment he met Frances Willard Vernon — nicknamed “Billie” — Cagney knew he had to have her. The couple tied the knot in 1922 and impressively remained together for the next 64 years.

During the Golden Age of Hollywood, it was typical of A-listers to carry on with countless affairs. Cagney, on the other hand, never cheated on Billie. The beautiful Merle Oberon tried to seduce him once during a USO tour, but the faithful husband resisted the temptation.

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However, Cagney’s hot streak came to an abrupt halt in 1960. Playing a soda-peddling businessman in the comedy One, Two, Three, the actor suddenly felt he lost a step. He was furious at himself for needing dozens of takes per scene, despite positive reviews from critics.

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So the A-lister simply stepped away — for decades, in fact. Cagney lived quietly with his wife, turning down big parts in classics like The Godfather Part II. With his health deteriorating, Hollywood insiders feared the legend would never come out of retirement.

But after 20 years away, the actor stepped back on set. He appeared in a supporting role in the period epic Ragtime, which initially terrified the rest of the cast. However, Cagney emerged as a wonderful mentor, and it came as no surprise when he received an Oscar nomination.

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Sadly, the film icon never took on another part. He died of a heart attack in 1986 and had a funeral that was packed with esteemed collaborators and friends. Ronald Reagan, right in the middle of his second presidential term, delivered Cagney’s eulogy.

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Hollywood stars were often amazed by Cagney’s warmth, a far cry from the callous criminals he often portrayed. The actor had a way of gaining access to the innermost lives of his friends, especially frequent co-star and confidante Humphrey Bogart.

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1. Bogart’s trademark lisp has become one of his many calling cards, though the impediment nearly cost him his career early on. In fact, Warner Bros. studio head Jack Warner actually hesitated to cast him in major roles because of it.

2. In addition to being an A-list actor, Bogie was also an expert chess player. He frequently out-hustled chess hustlers at corner stores and once beat 40 opponents in a single day.

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3. For his role in 1951’s The African Queen, Bogart was asked to do a cockney English accent. When it was revealed that he couldn’t, his character was switched to a Canadian instead.

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4. Though the “Rat Pack” moniker is often associated with the likes of Frank Sinatra and Dean Martin, it was Bogie that was the group’s first leader. The term was actually coined by Lauren Bacall, who called the group “a damn rat pack” after a night of heavy drinking.

5. Bogart was born the eldest child of Belmont DeForest Bogart, a cardiovascular surgeon, and Maud Humphrey, a commercial illustrator. As such, his family was incredibly well off, though his parents fought often and rarely showed emotion toward their children.

6. For 1941’s The Maltese Falcon, a single statue was handcrafted for use in the production. Bogie actually ruined the original when he dropped it during filming, forcing the studio to have a second one made.

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7. Along with his association with the film itself, Bogart is often linked to his famous Casablanca line “play it again, Sam.” Like many other famous film lines, however, this is a misquote, as the actual line is “play it once, Sam.”

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8. While shooting 1948’s The Treasure of the Sierra Madre, Bogart was routinely taking hormone shots in the hope of conceiving a child with Bacall. Unfortunately, the shots made his hair fall out, forcing him to wear a wig throughout the production.

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9. Despite Casablanca being his most memorable performance, Bogie didn’t like the film at all. In fact, Orson Welles once claimed that Bogart called it the worst film he’d ever made!

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10. After being expelled from the prestigious Phillips Academy, Bogart joined the U.S. Navy in the spring of 1918. Though his time serving was short, Bogie actually went on to play a naval captain in 1954’s The Caine Mutiny.

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11. In 1989 32 years after his death Bogart made his final acting appearance in the Tales From the Crypt episode “You, Murderer.” Using unreleased footage, CGI, and a celebrity impressionist, Bogie was brought back from the dead for one final performance.

12. It’s no secret that Bogart was a heavy smoker, puffing two packs of Chesterfields a day. Following his esophageal cancer diagnosis in January 1956, Bogie bit the bullet and switched to filtered cigarettes instead.

13. Bogart’s first film, the ten-minute short Broadway’s Like That, was actually lost until 1963. However, the film’s soundtrack still hasn’t been recovered, leaving it a virtual silent film even today.

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14. Believe it or not, Bogie actually had a bit of royalty in his blood. Through American colonialist Thomas Woodford, Bogart and Princess Diana of Wales were ninth cousins once removed!

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15. Despite 1944’s To Have and Have Not marking the start of Bogart’s relationship with Lauren Bacall, tensions with director Howard Hanks nearly ruined the love affair. Hanks, who’d also fallen for Bacall, tried everything to ruin the relationship until Jack Warner ultimately intervened.

16. During the filming of The Maltese Falcon, Bogart and his co-star Peter Lorre tried to smoke in as many scenes as possible to annoy Jack Warner. Well, it worked, and Warner threatened to fire them if they didn’t stop.

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17. For years, a prevalent rumor asserted that Bogart’s recorded birthday, December 25, was a creation of studio executives and that his real birthday was actually the 23rd. This proved just a rumor, as Bogart celebrated his birthday on Christmas Day for his entire life.

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18. Bogie wasn’t much of a crier, but he always had an unusual soft spot for the original A Star is Born. Every Christmas Day, Bogart would invite friends over for a viewing of the classic film only to excuse himself in a fit of tears midway through.

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19. A frequent co-star of Bogart’s, George Raft actually turned down many of the roles that made Bogie famous. The leads in The Maltese Falcon, High Sierra, and even Casablanca were all offered to Raft before Bogart took them.

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20. Bogart’s first child Stephen was actually named for his character Steve Morgan in To Have and Have Not. Yet the young Bogart didn’t just inherit a name from his father — he inherited the spotlight, too.

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When Stephen Bogart first opened his baby blues in 1949, the little tyke had no clue he was already kind of a big deal. His parents were two of the most revered stars of the iconic Golden Age of Hollywood: Lauren Bacall and Humphrey Bogart.

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Previous to becoming a dad, Humphrey cemented his spot as acting royalty. His star took time to rise, but he quietly impressed in his initial acting roles. Evolving from Broadway to Hollywood films, Humphrey found the big break that defined him as a gangster extraordinaire in The Petrified Forest.

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Audiences grew used to Bogie in tough-guy gangster roles, so it came as a pleasant surprise when Casablanca unveiled the romantic hidden beneath those heavy-lidded eyes. This tender side was all too familiar to his future wife — Lauren Bacall.

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Bacall herself won the hearts of audiences, critics, and Humphrey right from her silver screen debut. The first film she appeared in was their romance-adventure To Have and Have Not. From then on the pair were inseparable.

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Early in their love story scandal reigned supreme: Humphrey was already married and Bacall was just 19 to his 44-years-old. Scheduling fueled their electric chemistry, as they continued right into subsequent production for their next film, The Big Sleep.

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Three months after the ink dried on Bogie’s divorce papers, he and Bacall, whom he fondly called Baby, swapped vows in a quaint countryside ceremony on May 21st, 1945. But that didn’t slow down their careers.

During their honeymoon period, the actors made two more films together, Dark Passage and Key Largo. As their relationship grew stronger, they set their sights on a new milestone.

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After sewing up their latest film romances, Bogart and Bacall decided it was time to start a family. Welcoming their son, Stephen Humphrey Bogart, named for a character in the movie they met making.

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Soon, the power couple welcomed a second child, daughter Leslie Howard, in 1952. Of course, they continued their tradition of using their films as name inspirations, taking hers from Bogart’s costar in The Petrified Forest.

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Leslie grew up and pursued totally not entertainment-related endeavors, becoming a nurse and passionate yogi. She shares her passions with husband, prominent yoga guru and author Erich Schiffmann.

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The usually private, Leslie gave a rare interview to Harper’s Bazaar about her parents in 2015. She remembered, “My mother always described my father…as very sentimental and romantic. He often gave her beautiful jewelry — and almost every piece was engraved with a sweet sentence or thought and his initials or name.”

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With three failed marriages in the books, it took Humphrey a while to find his truest love. Both of them publicly and privately adored each other. So, it was tragic and unfair that their marriage and family life came to an abrupt, and rather grim, end.

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The film Goliath is remembered for his toughness and a particular brand of masculinity. But sadly, Bogie wasn’t invincible. When the doctor delivered the news his terminal diagnosis he felt destroyed: esophageal cancer.

Only a few final months together followed. Bacall later recalled in her memoir the torturous decline. She wrote: “He looked so unlike Bogie — still mercifully unconscious…enclosed in another world, protected not by me, but by those raised bedsides, with those bottles and tubes sustaining life.” He died at 57 years old in 1957.

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After his father’s death, Stephen recalled what life was like being raised by his single mother. “I think she eventually started to do things she wanted to do for herself,” he said. “She always wanted to move back to New York because her mother lived there. And I think that was important for her. And she also got into theater.”

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Bacall remarried in 1961 to actor Jason Robards, and eventually gave her son and daughter a half brother named Sam. Ultimately the marriage didn’t last; alcohol addiction led to their divorce in 1969.

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Sam was the only one of Bacall’s children to inherit the acting gene. His most notable role was as Henry Swinton in Steven Spielberg’s A.I. Artificial Intelligence. Plus he nabbed a Tony Award for Best Actor in the 2002 play The Man Who Had All The Luck.

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Talk about pressure to succeed. Sam commented on his unique position, “They made me realize what the dedication of a professional was. I’ve often found myself doing a scene and then realizing, ‘Gee, I’m playing my father in this scene.’ My mother is probably a little discouraged with me because I’m not quite as intense about standards as she is.”

Of Bacall’s children, Stephen has definitely been the most forthcoming about growing up a Bogart. He published a memoir in 1995 called In Search of My Father, which largely unraveled the thought process of losing his famous father at just 8 years old, and slowly coming to realize his mammoth legacy.

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“When my father died there were 3,000 people I didn’t know at the funeral,” he said. “I figured there was something different. And there certainly was.” For Stephen, it’s difficult to untangle the unfairness of Humphrey Bogart existing forevermore on the silver screen when his children got so little time to get to know the off-camera version of their father.

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No matter what Stephen accomplishes, he wears, honorably, a “big red-lettered label that hangs from me. It doesn’t say ‘Steve.’ It says, HUMPHREY BOGART’S SON.” It’s a daunting task to walk in the wake of Bogie’s legacy, but Lauren Bacall taught her children to wear their last name with pride.

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In his book, Stephen described the lessons Bacall ingrained in them that their father never could, “She wanted me to remember that he didn’t like to lie,” he said. “He wasn’t a liar. She always used to pound that into me. Don’t lie. Tell the truth. That was a big deal.”

Stephen explained that even though his mother moved on, her heart always belonged to the late Humphrey Bogart, “She would talk about him all the time. It was almost like, ‘What would your father think?’ or ‘Your father believed in treating people correctly.'”

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Bogie notoriously loved sailing, and Stephen recalled a cherished memory on the family yacht Santana. “Eventually, finally, when I learned how to swim, we would go out on the boat,” he said. “I remember going to Catalina Island and swimming back to the Santana. I made it and he was very proud of me at that time…That kind of pride sticks with you.”

Stephen was struck by the example of true love he recognized in his parents despite his young age. After long days on set, the lovebirds would share an intimate dinner, without their children, as a special reprieve just for the two of them.

Call it what you will, but the Bogart Bacall household prioritized date nights. “It was the age in the ’50s when kids were seen, not heard. Parents had dinners — at least my mother and father did — with the adults. But they were in love. And they were good together. They were man and wife.”

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Speaking about what drew his parents together, Stephen acknowledged the obvious, “She was pretty good looking. She was 19, and he was 44. But I think it was her strength. She was a strong woman. She didn’t take crap from anybody. He thought she was very talented as well, but she could also keep up with him.”

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Stephen and his siblings laid their mother to rest in 2014. Bacall died at age 89, after a long, beautiful life. She was buried in the same final resting place as her late husband, and other notable forces of Hollywood, in Forest Lawn Memorial Park in California.

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In the wake of his mother’s passing, Stephen was asked by Fox News about what he missed most about his mother. Growing up with one parent, the loss affected him deeply, “Just the fact that she’s not here anymore,” he said. “Being able to talk to her.”

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He revealed that the end of Lauren Bacall’s life was a challenge. Her outgoing, vibrant personality was restricted to mostly staying in bed. “She was used to getting up and doing things, going out. She had assistants there for her all the time if she needed them. But I think it was a very tough time for her, those last few years.”

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Stephen, now in his seventies, lives in Florida with his wife. They share 3 children and dote on their 1 grandchild. A documentarian, author, and news producer, he never bothered with the family trade. “How do you compete with that?” he mused. “The comparisons would have been obvious. No, never.”

Sheepishly he added, “Plus, I was lousy at it. I was in a couple of plays in high school. I wasn’t very good. I couldn’t do it…It’s not an easy thing to do, to be someone else.” Instead, he honors the family by serving as the co-managing partner of the Humphrey Bogart Estate, he’s vowed to uphold and preserve his father’s legacy.

In 2018, they lent Bogie’s name to a brand of spirits; Humphrey himself loved a well-made drink. “He preferred gin and whiskey,” Stephen said. “Some of his favorite cocktails were martinis — which were made with gin in those days — gin and tonics, Manhattans and Old Fashioneds.”

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Each year, Bogart Film Festival pays tribute to Stephen’s famous father, “We’re trying to do stuff that will reach a lot of people. We try and do things that not only keeps him alive but [also] classic Hollywood alive. There’s a lot of great movies now…but I think there’s still room for classic Hollywood.”

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It’s guaranteed that generations ahead will still fondly celebrate the cigarette-in-hand, smooth-talking Humphery Bogart. Not just for his iconic filmography, but for his once-in-a-lifetime romance with his most beautiful leading lady, Lauren Bacall.

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