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Flynn's Last Fling

Near the end of his life, Hollywood's greatest swashbuckler embarked on one final adventure-the Cuban revolution
Gaspar González
From the Print Edition:
Tom Selleck, Nov/Dec 2007

In the summer of 1956, Errol Flynn traveled to Havana to star in The Big Boodle, a low-grade crime drama about a casino croupier who stumbles across a counterfeiting ring. It was a far cry from the big-budget, high-flying epics that had made Flynn a star 20 years earlier, but, then, the 47-year-old was no longer the dashing swashbuckler. "He was semi-retired," recalls Guillermo Alvarez Guedes, at the time a young Cuban television actor cast in the film. "He was up to something like 300 pounds, from not working. I heard he went to Brazil to get ready for the role."

If he did, the regimen didn't take. When Flynn showed up on the set—the casino interiors were filmed at the famed Hotel Nacional—he was overweight, drinking heavily and had trouble remembering his lines. Nevertheless, Flynn continued to exude a certain aura. "He was the prototype of the Hollywood star," says Alvarez Guedes, who today is a well-known comedian and radio personality in Miami. "He was very adept at causing a commotion and grabbing the headlines."

Since the mid-1930s, Flynn had been one of Hollywood's highest earners, one of its most renowned bons vivants and its most notorious star. But in many ways, his most intriguing role still lay ahead. In Cuba, a couple years after making The Big Boodle, Flynn would become involved in a burgeoning revolution, playing opposite a new kind of international star, one not confined to the screen: Fidel Castro. It would prove to be a most memorable experience, even for a man whose life had been one long series of improbable exploits.

Born in the Australian territory of Tasmania in 1909, the preternaturally handsome Flynn had come to Hollywood almost by chance. After trying his hand at a number of jobs, including plantation overseer, gold prospector and even correspondent for The Sydney Bulletin, he had drifted into acting. When a Warner Bros. talent agent spotted him doing bit parts in its English studio films in 1934 (following a stint with a British repertory company), he signed the 25-year-old to a modest contract of $150 a week.

Once in Hollywood, Flynn didn't have to wait long for his big break. In 1935, he was cast as the lead in Captain Blood, the tale of an eighteenth-century Irish doctor forced to become a pirate. It became one of the year's most popular films and it cemented a partnership between Flynn, director Michael Curtiz and costar Olivia de Havilland that would last for the next five years and produce such classic action films as The Charge of the Light Brigade, The Adventures of Robin Hood and Santa Fe Trail. (The excitement on-screen apparently spilled over onto the studio lot: Flynn and the tyrannical Curtiz clashed violently and often, while Flynn and de Havilland are rumored to have carried on a long-running affair.)

Playing a succession of larger-than-life heroes—not only Robin Hood, but Indian fighter George Custer, nineteenth-century heavyweight boxing champion Jim Corbett and legendary lover Don Juan—Flynn became something of one himself. Blessed with an athlete's natural grace and a rogue's charm, he was a compelling screen presence and, perhaps to a greater degree than any of his contemporaries, the era's cinematic ideal of what a man should be.

It was a status that turned out to be both a blessing and a burden. A well-publicized statutory rape trial in 1942, in which Flynn was charged with having sex with two different underage girls on different occasions, cast a harsh light on his private life. Movie fans discovered what Hollywood insiders had long known: despite his marriage to actress Lili Damita, Flynn essentially lived the life of a bachelor, one with a predilection for young girls. "He liked to teach women and women liked to learn from him," says daughter Rory Flynn, the product of the actor's marriage to second wife Nora Eddington. "He was a man who never had to chase women, and who would never say no. He would never deny himself." Or, as Flynn himself once put it: "If you meet a young lady who, in fact, invites herself for a trip on your yacht...knowing in advance full well what the risks are, who the hell asks her for her birth certificate, especially when she is built like Venus?"

Though Flynn was acquitted of the charges, the trial was a humiliating experience for him. Most regrettable, he believed, was the famous phrase it spawned: "In like Flynn." A pointed reference to the movie star's easy way with the ladies, it remains a familiar expression to this day, even if few people know its origin.

The rape trial, for all the negative press it generated, did little to diminish Flynn's appeal at the box office. More damaging to his career was the postwar shift in Hollywood films, away from costume dramas and toward gritty, contemporary urban storylines with psychologically complex characters. It was a cultural sea change that largely relegated Flynn to second-tier stardom. In 1952, he and Warners parted ways.

For the next few years Flynn produced and starred in European films and even took work in television—at the time, a fledgling medium that few screen stars would deign to grace. "He went around hustling for money," his daughter says, "but he was drinking. Nobody would touch him." With his finances in disarray—to go along with his professional woes and years of reckless spending, he discovered his business manager had been stealing from him—Flynn was probably only too happy to pack his bags for Havana in May 1956.

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